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Things To Do | Get yourself on a boat: The best booze cruises…

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Things to do | get yourself on a boat: the best booze cruises in chicago.

For three months, Chicago’s weather permits us to spend prolonged periods of time outdoors, and we always make the best of it. That includes pretending like we’re living in an island paradise and drinking memories of winter away. On a boat.

Grab your life-jackets and your goggles (beer or otherwise) and head to these 14 booze cruises to work on your sea legs while getting raucously drunk.

Island Party Boat Monroe Harbor, 312-600-8454 If you’re OK with bordering on tacky, take an Island Party Boat booze cruise along the Chicago River. For $30, you can spend an hour drinking to excess against a soundtrack of ukulele tunes and pretending the water below you isn’t an unnatural color. Dogs are allowed to join you so long as they aren’t scared of drunk strangers. Tickets: islandpartyboat.com .

Mystic Blue Craft Brew Cruises Navy Pier, 866-391-8439 If your drinking preferences are on the refined end of the spectrum, Mystic Blue’s craft brew events are perfect for you. Throughout the summer, the boat will play host to a few select events featuring only the best of Midwest beer and ciders—and one day that’s all about Belgiums brews. Prices range from $39.90 to $49.90 per person. Tickets: mysticbluecruises.com

After Work Cruises aboard Anita Dee II Navy Pier, 866-261-9330 Every summer night is a night for drinking, right? On Monday and Tuesday nights, hop aboard the Anita Dee II at Navy Pier for three hours of sailing and boozing with other professionals drinking off the two hardest days of the week. These two cruises run from 6-9 p.m. with tickets starting at $25 per person. Tickets: afterworkcruises.com

Chicago Cocktail Cruises at Navy Pier Navy Pier, 866-273-2469 Up your boat drinking game with these craft cocktails on offer aboard this skyline cocktail excursion. Starting at $44.90 a person, you’ll have from 3:30-6 p.m. to eat hors d’oeuvres, shake your groove thang on a DJ’d dance floor and mingle with other Chicagoans (and probably some tourists) just trying to live their best lives. Tickets: spiritcruises.com

Eat, Drink & B. Mary Brunch Cruise Navy Pier, 866-273-2469 Why not take your usual Sunday brunch out on the water? This two-hour cruise on Lake Michigan will serve up not only your brunch favorites buffet-style, but also bloodies and mimosas for you to sip to your heart’s content. Tickets start at $57.90. Tickets: spiritcruises.com

Friday and Saturday Night Booze Cruises with Chicago Party Boat DuSable Harbor If you’re OK with being surrounded by a bunch of drunk 20-somethings trying to cling to their college days, this cruise is the place to be. Ranging $20-$50 depending on the date and the occasion, these cruises feature a live DJ. Tickets: chicagopartyboat.com

Beer and BBQ Cruise with Wendella Boats 400 N. Michigan Ave. 312-337-1446 Make Ron Swanson proud on this two-hour cruise down the Chicago River to Lake Michigan. Sip craft beer while you nosh on barbecue offerings courtesy of Sweet Baby Ray’s. Tickets start at $53.75 and tours run from 5:45-7:45 p.m. every Thursday. And if the weather doesn’t hold up, no sweat. Each boat includes climate-controlled lounges so your money won’t go to waste. Tickets: wendellaboats.com

Wine and Cheese Cruise with Wendella Boats 400 N. Michigan Ave. 312-337-1446 The finer things in life await you on the high seas—er, lake—of Chicago with this wine and cheese-devoted event taking off every Thursday at 5:45 p.m. along the Chicago River. Wine and cheese pairings from Pastoral make this the highest-class trip you’ll find on the Great Lakes. Tickets: wendellaboats.com

Summer Brew Cruises with Revolution Brewing Navy Pier, 312-222-9328 Celebrate Chicago’s craft beer connoisseurs at Revolution on this brew cruise featuring seasonal craft beer tasting, appetizer pairings and views of the Chicago skyline. For $49 per person, take in the sights and sounds of the city for 90 minutes while you sip on your favorite Revolution beer to the soundtrack of live music and hipsters discussing the different flavor profiles. Tickets: shorelinesightseeing.com

Illinois Made Cruise Navy Pier, 312-222-9328 All things Illinois will take center stage on this 90-minute ride around the shoreline. For $49 per person, dabble with different food and drink vendors from across the state, all while appreciating the Windy City we call home. Tickets: shorelinesightseeing.com

Hard Cider Tasting Cruise Navy Pier, 312-222-9328 Beer isn’t for everybody—or so we’ve heard—but cider is a good substitute. This $49 per person cruise features a lineup of different grown up apple juices, both local and from across the country. For the uninitiated, the tasting cruise will begin with a lesson in how to properly sip a cider … or you can say “screw it” and throw it back. Tickets: shorelinesightseeing.com

Wine Tasting Cruises with Lynfred Winery Navy Pier, 312-222-9328 Keep it classy with this wine tasting (read: not chugging) along the Chicago skyline. Hosted by Illinois’ oldest family-owned winery, this cruise will kick off with a wine course and “generous” tastings of Lynfred’s most popular selections. A fancy summer night awaits you. Tickets: shorelinesightseeing.com

City Winery Wine Flight River Cruises 11 Chicago Riverwalk, 888-636-7737 Leave your three buck chuck at home and hop aboard this Seadog cruise by City Winery. Spend 75 minutes admiring Chicago’s architecture with a guided tour of the city as you sip on select City Winery favorites. Tickets range $41.95-$53.95, depending on how much wine you’re looking to throw back in an hour and a half. Tickets: seadogcruises.com

Chicago Line Architecture Cocktail Cruise 465 N. McClurg Court 312-527-1977 Sponsored in part by the Chicago History Museum, this architecture cruise is equal parts boozy and informative. For $21 on top of your admission, you’ll have access to unlimited wine, beer and mixed drinks during your 90 minutes aboard the boat. Regular admission starts at $43. Tickets: chicagoline.com

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8 Best Chicago Booze Cruise Events Happening This Weekend

Take a trip down the Chicago river and on Lake Michigan, all while enjoying some cocktails, music, and a memorizing view!

Is there a better way to spend a summer afternoon than cruising around the Chicago River with some boozy drinks ? We think not! Now that summer humidity is upon us, it’s time to grab your crew and hit Lake Michigan for all-around blissful entertainment. This is the perfect time to set sail on a Chicago booze cruise if you enjoy sipping on tasty cocktails , dancing the evening awa y, and taking in Chicago’s majestic skyline.

1. Swiftie Booze Cruise 

Attention all Swifites—have you ever just wanted to shake it off on the Chicago River? While Taylor Swift takes her tour internationally, you can pretend you left Chicago for a few hours as you listen to all your favorite T-swift songs to Lake Michigan. Enjoy music, drinks, and great company as you take in breathtaking city views through the river and into the lake.

📍 Location : 900 S Wells St, Chicago

👤 Age requirement : 21+ with valid ID

🎫: Purchase tickets to the Swiftie Booze Cruise here

2. Labor Day Sunday Funday Sunset Booze Cruise

Celebrate Labor Day the right way with a fun party cruise on the Chicago River. On this booze cruise, you’ll sail all along the river until you reach Lake Michigan, where you’ll dance the night away to your favorite tunes. With some of Chicago’s best house music artists and two fully-stocked bars, you’ve got everything you need to make a memorable Labor Day weekend.

📍 Location : 900 S. Wells St., Chicago

🎫 Purchase tickets to Labor Day Booze cruise here

3. Boozy Brunch Cruise

Prepared to be enthralled with the Chicago aroma—the city and the delectable scents of a morning brunch—all while becoming slightly tipsy from the endless mimosas. If that doesn’t convince you, the Dj’s electrifying beats just might. Think about it—as you soar down the river, the wind in your hair, you’ll be frocking with dazzling skyline views and delightful music. This Chicago booze cruise will have your taste buds in overdrive while catering to your rumbling stomach. 

📍 Location : TBD

👤 Age requirement : None

♿ Accessibility : Wheelchair Accessible

🎫 Get your tickets to Chicago Signature Brunch Cruise here

4. The Lake House Day

Save the trip to Michigan, Wisconsin, or another small town near Chicago for another day because, believe it or not, your party lake day awaits you on the Chicago River. This Chicago booze cruise will have intoxicating house music reverberating on the boat. As you admire breathtaking views , you’ll be swinging and turning with delicious drinks in your hands. It will probably be hard to get off this Chicago booze cruise.

📍 Location : 900 South Wells Chicago, Illinois, 60607

🎫 Get your tickets to “The Lake House” Day Cruise here

 5. Sunday Funday Booze Cruise

Have you ever stayed up until sunrise, still slightly inebriated, and thought to yourself, “How do I keep the party going?” Your wishes have been answered—set sail and experience the ultimate party at the Sunday Funday Booze Cruise . Once stepping aboard, the music will blare, and you’ll be dancing to a DJ’s mix of songs you can’t get out of your head—all of this and multiple cocktails in hand. There is no slowing down on this Chicago booze cruise as you speed through the river and watch Lake Michigan glimmer.

📍 Location : 9 00 South Wells Chicago, Illinois, 60607

🎫 Get your tickets to Sunday Funday Booze Cruise

6. Sights & Sips 

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If house music isn’t your thing, and you want to experience a more decadent booze cruise, Sights & Sips is the place to go. This cocktail cruise has creative cocktails, wine, beer, and a full list of scrumptious Hors D’oeuvers, including bruschetta, skewers, a Mediterranean station, and more. For a few hours, you can cosplay guests from Below Deck and enjoy being catered to as revel in Chicago’s views.

📍 Location : River Esplanade 455 N Cityfront Plaza Drive Chicago, IL

👤 Age requirement : none

🎫 Get your tickets to Sights & Sips here

7. Chicago River Architecture

Boozy history is one of our favorite activities—is there anything better than spending the day sailing down the river, learning about the architecture with a drink in hand? The Chicago Lake and River Architecture Tour  happens to have all that and is one of our favorite tours.

📍 Location : 400 N Michigan Ave Suite C100, Chicago, IL , 60611

🎫 Get your tickets to Chicago Lake and River Architecture Tour here

8. Floating Tiki Bar Cruise

In Chicago, we’re one of the few cities where we can dig our toes beneath the sand and jump into the waves to cool off; even with humidity at an all-time high, we’re still far from a tropical paradise with palm trees and coconut-sippy cups.

However, one way is to head to a tiki oasis without spending hundreds on a plane ticket. At this floating tiki bar, you can cruise down the Chicago River while soaking in tropical tunes and the city’s stunning architecture.

This is a unique tiki Chicago booze cruise experience, from bascule bridges to the Tower buildings. 

📍 Location : 355 Chicago Riverwalk, 60601

👤 Age requirement : 21+ with valid ID to consume alcohol

♿ Accessibility : Not Wheelchair Accessible

🎫 Get your tickets to the Floating Tiki Bar Cruise here

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River Cocktail Cruises – Odyssey Chicago River

• 455 N Cityfront Plaza Dr Chicago 60611
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Take a late afternoon detour during a two-hour cocktail cruise on the Chicago River. This experience is ideal for anyone seeking lighter fare and a slightly shorter cruise time, while still enjoying stunning views and exceptional service.

What's Included

• A 2-hour cruise on the Chicago River aboard our new, all-glass vessel

• Incredible views of Chicago's iconic architecture (see route)

• Passed hors-d'oeuvres and light bites from our Cocktail Cruise Menu

• Cocktails, beer & wine available for purchase from our onboard bar 

• Odyssey Chicago River is docked at 455 N. Cityfront Plaza Dr

• Board: 3:30pm | Cruise: 4 - 6pm | Price: starting from $64.90*

• Mon-Fri Closed
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The 15 best boat tours in Chicago

See the skyline from dazzling new vantage points aboard one of the best boat tours in Chicago

Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights – but the best way to see downtown Chicago is from the water. Both the Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline , with many of the tours providing unique insights into the city’s culture and history.

From architecture tours and history lessons to  straightforward sightseeing affairs , romantic excursions and pirate-themed family fun, there's a Chicago cruise for every groove. Below we’ve got the essential list of the city’s finest waterborne tours, including tall-mast ships and glitzy speed boats. Bon voyage!  

RECOMMENDED: Find more to explore with the best things to do in Chicago Plan your trip with the  best hotels in Chicago

How do we determine the cream of the crop? Our staff picks combine the top, most recent reviews with some of our personal favorites to make sure you get the best deal on the web. Throughout this article, you may notice some affiliate links – these have no influence on our editorial content – we pinky swear. For more information, see our  affiliate guidelines .

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Best Chicago boat tours

1.  1.5-Hour Guided Architecture River Cruise

Departing from Navy Pier's Polk Bros Park or the northeast corner of the Michigan Avenue Bridge, this 60-minute trip packs in all of the architectural sights that visitors want to see. Tour guides highlight more than 40 towering Chicago landmarks, including the Tribune Tower, the Wrigley Building, and Marina City (a.k.a. "The Corncobs" or " The Wilco Building "). 

Don't miss:  Locally sourced food and drink from the boat bar.  

2.  Seadog River and Lake Architectural Tour

There are few more iconic Chicago sights than seeing the bright yellow Seadog speeding around town. Combining speed and sightseeing, Seadog’s architecture tour whizzes guests past the likes of the Willis Tower and Lyric Opera, all while arming you with an impressive load of facts about the Windy City. And after this blustery 75-minute tour has finished traversing the Chicago River, it ends with a thrilling whizz across Lake Michigan, past Museum Campus, and Grant Park. This one departs from Seadog’s dock at Navy Pier throughout the summer months.

Don't miss:  Local beer, spirits and Garrett's Popcorn at the boat bar.

3.  Wendella: Chicago's Original Family-Friendly Architecture Tour

If you're weighing your options, Wendella's architecture tour (which it claims is Chicago's original ) is another way to explore all of the beautiful structures that line the river. Over the course of the 90-minute tour, you'll navigate all three branches of the Chicago River, while your guide fills you in on the stories behind some of the skyline's most prominent edifices. This tour departs from the Wendella Dock, located at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building.

Don't miss: Live commentary from the tour guide, with material to entertain the whole family. 

4.  1.5-Hour Romantic Sunset Cruise

How do you end the perfect day of sightseeing? With the perfect sunset, obvs. Setting off from Wendella Dock (at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building), this 90-minute cruise will breeze along Lake Michigan as the glint of the sun on Chicago's skyscrapers is replaced by twinkling city lights. 

Don't miss: Toasting to the end of the day with wine, local beer and hand-crafted cocktails.

5.  Tall Ship Windy Architecture & Skyline Sailing Tour

Let the wind carry you to stunning views of the city from aboard the Tall Ship Windy, a four-masted, 148-foot topsail schooner. The 75-minute trip cruise brings guests on a scenic route running along the Lake Michigan shoreline, where you can take in lovely skyline vistas and glimpses of the sunset. Head to the onboard bar to find snacks and drinks for sale. 

Don't miss:  Bring the kids for the special pirate-themed cruise, featuring  tales of swashbuckling  on the Great Lakes.  

6.  Seadog Speedboat Tour

If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park, and more.

Don't miss: Upgrade to the Extreme Thrill Ride, which includes full 360° spins and more. 

7.  Lake Michigan Skyline Sightseeing Cruise

Want to see Chicago from the water but don't have much time to spare? You can peep the skyline in just 30 minutes on Shoreline's Classic Lake Tour, which departs from Navy Pier and boasts some of the best views you'll find on Lake Michigan. The commentary on the city's architecture and history is pre-recorded, so you won't miss out on any information because your guide ran out of time (and if you've heard it before, you can sit back and enjoy those sweet, sweet sights).

Don't miss: Proceeding straight to the boarding line with a barcode that lets you skip the ticket office. 

8.  Lake Michigan Gourmet Dinner Cruise

Enjoy a three-course gourmet dinner on the water in the Odyssey Chicago, where you can enjoy breathtaking views of the skyline surrounding you. Departing from Navy Pier, this cruise includes a dinner with freshly prepared entrées, mains, and desserts. The 2.5 or 3-hour ride takes you around Lake Michigan, with a cash bar to keep the drinks flowing throughout your meal.

Don't miss: The live DJ set and unlimited tea and coffee.

9.  Chicago's Lake Michigan Kayak Tour

If you want to couple a workout with your sightseeing, consider touring Lake Michigan by kayak. The rental lasts one hour and if you've never kayaked before, don't worry – tandem kayaks are available for less experienced guests. The meeting point is at Ohio Street Beach and you'll be provided with a life jacket on arrival before paddling out onto Chicago's most incredible river view.

Don't miss: Take a break along the urban beachfront, with the chance to also rent stand-up paddle boards.  

10.  Lake Michigan Buffet Brunch Cruise

If you're looking for dinner with a view, you could do worse than watching the sunset against the skyline aboard this 2.5 or 3-hour Lake Michigan brunch, lunch, or dinner cruise. Grab a group of friends and book a table – ideally one with a window-facing view—for a buffet-style meal before making your way to the dancefloor for an evening of DJ-curated music. Unlimited coffee, tea, and water will be on hand.

Don't miss: Creative signature cocktails at the bar. 

11.  Lake Michigan Odyssey Gourmet Lunch Cruise

Why settle for lunch at a land-bound restaurant when you could eat your meal on Lake Michigan? The Odyssey's lunch cruise includes a three-course meal and all the coffee, hot tea, iced tea and water you can drink. Visit the cash bar to buy wine, beer and cocktails and enjoy the views on this two-hour tour.

Don't miss: Dance on the top deck to tunes played out by the onboard DJ. 

12.  Chicago Fireboat Tours Historical and Architectural Cruise

Hosted on the bright red Fred A. Busse Fireboat – which served the Chicago Fire Department until 1981 – this architectural tour of the Chicago River lasts anywhere from 90 minutes to two hours. A docent will fill you in on the history of buildings lining the river as well as the story of the boat you've boarded, which formerly traveled the city's waterways to fight fires. 

Don't miss: Check out the vintage firefighting artifacts and photos on board. 

13.  Lady Grebe Chicago River Experience

Want to feel extra posh? Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for two-hour trips along the Chicago River. The reservation comes with a premium drinks package and you can also opt to kick things up a notch with picnic baskets full of food or full-service catering. 

Don't miss:  Book a Chicago Architecture Center docent to give a guided tour for an educational twist.

14.  Chicago Electric Boat Company Tour

Go your own way. Be your own captain. That’s what’s on offer with this Chicago River tour. The Chicago Electric Boat Company lets passengers steer the ship themselves (if they’ve got a valid driver’s license and watched a 10-minute tutorial, that is), allowing total freedom on the Windy City’s waterways. If you’re looking to still have some kind of tour, you can hire a personal tour guide—and we haven’t even gotten to the best bit. These boats are all electric, so they’re a little bit more environmentally friendly, too.

Don't miss: Hot tub boat rentals are also available.

15.  Chicago Architecture Center River Cruise Aboard Chicago’s First Lady

There's a reason the Chicago Architecture Foundation's beloved tour has been named the Best Boat Tour in the U.S.  The center’s official tour goes into detail on more than 50 buildings both on the riverfront and beyond. In doing so, they give a fascinating history of the city and those that built it—plus you can easily upgrade your ticket to include entry to just Chicago Architecture Center itself. It’s a proper design enthusiast’s dream. This one leaves from the Chicago First Lady Cruises dock and lasts around 90 minutes. 

Don't miss:  Gather friends for the serene evening cruise for just a few dollars more.

GYG Chicago TTD

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Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

Our Cruises & Tours

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

Our Cruise Partners

Discover our partners: Spirit Of Chicago, Shoreline Sightseeing, Seadog Cruises, Odyssey Lake Michigan, Mystic Blue, Chicago Elite Private Yacht, & Tall Ship Windy

Cruise & Tour Types

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

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City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise. Departing from Navy...

City Cruises – Seadog River and Lake Architecture Tour

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way...

City Cruises – Seadog Lakefront Speedboat Tour

Our Lakefront Speedboat Tour is the best way to view Chicago from the lake, combining an exciting speedboat ride along the shoreline with informative and...

City Cruises – Seadog Extreme Thrill Rides

With exhilarating high speeds and full 360° spins, this jet-propelled ride blasts off to start and splashes down to stop. Experience full throttle slalom runs,...

City Cruises – Odyssey Lake Michigan Brunch Cruise

This two-hour brunch cruise on Odyssey Lake Michigan, departing from Navy Pier, is ideal for capping off an incredible weekend. Enjoy a delicious menu stocked...

City Cruises – Odyssey Lake Michigan Groups

Host a truly unforgettable event on Lake Michigan. Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event...

Shoreline Sightseeing Group Tours

Adventures are meant to be shared. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. We offer special...

City Cruises – Chicago Elite Private Events

It's your yacht. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. With two fully enClosed ,...

City Cruises – Seadog Groups

Planning a special outing for your group? Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,...

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing’s water taxis are a great way to get around town. Starting in May and running through September, our water taxi service offers fast...

City Cruises – Spirit of Chicago Group Cruises

Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or...

City Cruises – Premier Brunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all...

City Cruises – Signature Brunch Cruise on Lake Michigan

Shoreline Skyline Lake Tours

Shoreline’s 40-minute Skyline Lake Tour offers a relaxing way to experience the panoramic of the city’s famed skyline as seen from majestic Lake Michigan. The...

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy is closed for the season and will reopen in May 2024. Visit the Tall Ship Windy website to stay up to date...

Tall Ship Windy Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy...

Chicago River Architecture Tour

Chicago's Original Architecture Tour®

Experience the city’s legendary architecture from the best seat in the house—the river. Our experienced tour guides detail the 130 year long history behind the skyline, while our bartenders and staff keep you comfortable and entertained. This comprehensive tour navigates through the heart of the city on all three branches of the Chicago River. It’s the one thing everyone tells you to do in Chicago, done right.

Schedule & Tickets

• Adult: $44.00
• Child (4-12): $20.00
• Under 4: Free (ticket required)

TICKETS ARE NON REFUNDABLE BUT ARE TRANSFERABLE.

• Parking & Directions
• More Information
• COVID-19 Safety
• Boarding begins 15-30 minutes prior to scheduled departure time.
• All bags are subject to inspection.
• Prohibited Items: Outside Alcohol, Weapons of any kind (Firearms, Knives, etc.), Flammables, Explosives.

Your boat includes:

Drinks & Snacks

Full-service bar with wine, local beer, and craft cocktails, as well as an assortment of snacks, all for purchase. Pinkies up!

Expert Tour Guide

Never boring, always entertaining.

Accessibility

Everyone should be able to enjoy our tours. We make sure you can.

No need to hold it. We have changing tables for the little ones who don’t know what holding it is.

Climate-Controlled Lounge

Keeping you cool when it's warm and warm when it's cool (or freezing).

*Not all amenities are available on every vessel.

BOOK YOUR EXPERIENCE NOW

Your guide to Chicago lake and river cruises

One of the best ways to see Chicago is from the water. The city is home to two stunning waterfronts — the Chicago River and Lake Michigan — and each offers plenty of cruise options. Admire the skyline on a lakefront cruise, learn about the city’s iconic architecture on a Chicago River cruise, enjoy dinner and dancing aboard an all-glass vessel, sip cocktails on a tiki-themed boat, paddle your own kayak — the options are truly endless. Here’s your guide to Chicago lake and river cruises, boat tours, dinner cruises, and beyond.

See it all with Shoreline Sightseeing

One of Chicago’s classic cruise options, Shoreline Sightseeing covers all the bases. Their ultra-popular Architecture River Tour takes you on all three branches of the historic Chicago River takes you past dozens of landmark buildings.

They also offer skyline lake tours, plus specialty cruises and holiday events. Hop on a boat at Navy Pier or on Michigan Avenue.

Dine on the water with City Experiences

City Experiences dining cruises are the perfect way to create a memorable moment in Chicago. Choose from a river or lake dining cruise, complete with delicious cuisine, cocktails, and entertainment.

Their glass-enclosed river vessel is particularly stunning. It offers passengers panoramic views of the city’s most iconic buildings as you glide along the Chicago River. They also offer lakefront brunch and dinner cruise options that depart from Navy Pier.

Entertain the family with Wendella Boats

For three generations, Wendella Tours and Cruises has been cruising the Chicago waterways. With its variety of tour options, cruise times and lengths, and a heated, enclosed cabin, Wendella is a great choice for families looking for flexibility. Choose from lake & river architecture, sunset cruises, and more.

Admire architecture with Chicago’s First Lady

Around the world, Chicago is known for its outstanding architecture, and it’s easiest to admire the city’s legacy from the water. By partnering with the Chicago Architecture Center , Chicago’s First Lady offers the most comprehensive tour of the skyline — docents must train 100 hours before they can lead tours.

Speed across Lake Michigan on Seadog Boat Tours

Are you up for a thrill? Race across Lake Michigan on SeaDog Cruises, featuring 30 minutes of high speeds and exhilarating twists and turns. Come prepared to get splashed.

SeaDog also offers lakefront speedboat tours and a river/lake architecture tour, featuring views of Chicago’s iconic Buckingham Fountain, Grant Park, Museum Campus, and more.

Live it up on an Island Party Boat

Looking for a party? These tiki-themed boats are always a good time, offering drink packages, stellar views, and fun vibes. You can hop on an Island Party Boat at Monroe Harbor or the Chicago Riverwalk, which is also where you’ll find their beach-inspired bar Island Party Hut. Choose from a river cruise, lake cruise, tacky tour guide cruise, or even a dueling pianos cruise.

Go back in time with Chicago Fireboat Tours

Step onto a real, historic fireboat and get ready for a unique experience with Chicago Fireboat Tours . The river tours are given aboard a real piece of Chicago history — a retired fireboat that patrolled the Chicago from 1937 to 1981. Tours are led by expert docents and include historic and sunset options.

Splurge on a Free Spirit Yacht Cruises

Looking to splurge a little? These private yacht charters are the way to go. The spacious yachts comfortably fit up to 49 or 120 people, making them the perfect option for a large celebration or an intimate gathering. Premium bar and catering packages round out the experience.

Explore the Chicago River with Urban Kayaks

If you’re ready to ditch the captain and explore the water on your own, then it’s time to grab a paddle at Urban Kayaks . You’ll go through a brief training session before you hit the water, but you’re free to paddle the river or lake at your own pace. Or join in a guided tour to catch the sunset, fireworks, or historic highlights. Rentals are available at the Chicago Riverwalk or Monroe Harbor.

Rent an electric boat

Chicago Electric Boat Company offers fun and unique ways to get out on the water, including donut boats, retro boats, and even a bike boat that your group can pedal down the Chicago River. Rental locations include Marina City, the Chicago Riverwalk, and Rockwell on the River in Avondale.

See the skyline aboard Mercury Cruises

While Chicago’s summer fireworks are already fun to watch, it’s an entirely new experience when you’re on a 3D tour. Before the show, you’ll cruise around the lake and see some of Chicago’s famous landmarks.

Mercury Cruises also offer Urban Adventure, Canine Cruises, and Chicago by Night tours.

Check out Chinatown via Chicago Water Taxi

Hop on! The Chicago Water Taxi is a fun and cheap way to get around Chicago. The Water Taxi stops at Ogilvie Transportation Center, Chinatown, Goose Island, the Chicago Riverwalk, Michigan Avenue, and River North. Get a one-way ticket for $6 or an all-day pass for $10. Check their daily routes and schedules for more details. Cruises.

From this article

Tours & Attractions

Chicago architecture center.

Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing Company

Streeterville

Special Event Venues

Free spirit yacht cruises.

Urban Kayaks

River North

Wendella Tours & Cruises

The Magnificent Mile

Chicago’s First Lady Cruises

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CHICAGO BY NIGHT! Cruise

See Chicago's skyline sparkle and glow as you glide along the Chicago River and Lakefront under the dazzling glow of the city by night. 

THANKS FOR A GREAT 2023 CRUISING SEASON

2024 tickets on sale now!

See Chicago Twinkle and Glow

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night. Hear lively commentary as you feel the night breezes and see Chicago’s dramatic skyline transformed into a glittering jewel. Family-friendly boat tours are our specialty!

Priority boarding now available!

• Includes exclusive early boarding period • Skip the queue during general boarding

Ticket Price

• Adults (Priority Boarding) $47
• Adults (General Boarding) $42
• Kids 5-15 (Priority Boarding) $24
• Kids 5-15 (General Boarding) $19
• Under 5 Free

Call us for group reservations at 312-332-1368 or contact us at [email protected] (group rates available Sunday - Friday).

Ticket Pricing

Full schedule.

May 24 - October 14 Departing Monday, Thursday, Friday & Sunday at 8:15pm

Located on Chicago’s Riverwalk

On the Chicago Riverwalk just off The Magnificent Mile

We love groups!

A fun, relaxing, informative boat tour along Chicago's beautiful waterways is the ultimate way to experience the city and leave a lasting impression on your group.

“The city lit up at night was beautiful, and our guide was both entertaining and informative. We highly recommend this tour. Also, you get foam light-up sticks, which is fun!”

Julie G., Facebook

Frequently Asked Questions

No. Reservations are not necessary for daytime tours, though you are welcome to purchase tickets in advance online . We also encourage advance purchase online or dockside if you desire to cruise a particular date and time and want to guarantee your seats aboard.

We do advise that you buy CHICAGO BY NIGHT! and 3D Fireworks Cruise tickets in advance – online or at the box office – as these tickets are extremely popular.

Online we accept Visa and MasterCard. At our dockside ticket office, we accept cash, Visa and MasterCard.

Beverages – including water, soda, canned cocktails, beer, and wine – are available for purchase on board. Please note, no outside alcoholic beverages are allowed.

Snacks - including small items such as chips, cookies, and nuts - are also available for purchase.

Please note that all ticket sales are final.

All of our Urban Adventure Cruise and Chicago By Night! tours pass through the Chicago River Lock System. Our guide/narrator gives a full explanation of the operation of the lock. You’ll feel the boat rise as you enter Lake Michigan and lower as you return to the River. Saturday departures for our 3D Fireworks Cruise also go through the Chicago River Lock.

Yes. Our cruises depart rain or shine. We have open and covered seating on board.

Yes, of course! There are "Heads" located on board as well as one lined with newspapers for your dog(s) during the Canine Cruises.

The safety of our guests and crew is our number one priority. After more than 80 years providing memorable cruises of the Chicago River and Lake Michigan for millions of guests, we are proud to say we have a perfect safety record.

All of our vessels are regulated, licensed and inspected by the United States Coast Guard (USCG) every year, and have undergone stability testing to ensure our guests are safe on their waterway experience. Our captains and deckhands go through an extensive training and drilling program that goes above and beyond the standards set by the USCG. Because we are committed to continuing education, we provide extra training every day to our crew.

If you have any questions about our safety training protocols or other concerns, please contact our Company Security Office Captain Tom Hacker at [email protected].

No. Luggage is not allowed aboard the Mercury vessels. Please leave your luggage at your hotel or check your bags in at a hotel near the dock (be sure to confirm in advance the ability for the hotel to accommodate you). Also, please be aware that all bags (purses, backpacks, etc.) are checked before boarding.

Yes, strollers may be brought aboard and will be folded and stored in the indoor salon for the duration of the cruise. They are not allowed on the deck. Please note, children must be removed from strollers before boarding.

In accordance with ADA guidelines, we welcome service dogs onboard. The service animal must be harnessed, leashed, or tethered while in public places unless these devices interfere with the service animal's work or the person's disability prevents use of these devices. Emotional support animals, pets and other animals not covered by the ADA are not permitted. All dogs are welcome on  Mercury's Canine Cruise ! Please visit the ADA's FAQ on service animals for further details. 

We love groups and would be happy to offer you a group discount if you would wish to reserve in advance! Please call 312-332-1368 or [email protected] for more information! 

Please note that we do not offer group discounts for our 3D Fireworks Cruise, but are happy to make a group reservation for full price! 

Boarding begins 15 minutes prior to scheduled departure time. Choose any seat - all offer a great view!

Children under 5 are always welcome free of charge, but do still require a ticket. Folded strollers may be brought on board. Children’s rates available for kids 5-15 years old.

At this time the Riverwalk does not offer any elevators. For those who need ADA ramps, you may access the Riverwalk via the ADA ramp at State Street and Wacker Drive within the Vietnam Memorial Park. Then just follow the Riverwalk to the East under the Michigan Avenue Bridge. Our Ticket Office is marked with a blue awning. Our stairway offers handrails, and shade from the sun. For guests needing special vehicle drop-off assistance, click here for Mobility Assistance directions.

For safety reasons, motorized scooters and electric wheelchairs cannot be accommodated aboard the ship. Guests who can transfer may use the company's manual wheelchair, based upon availability. Please note guests using manual wheelchairs must be accompanied by individuals who are capable of assisting/lifting the wheelchair over the boat’s threshold. Under Federal law and due to special marine safety construction guidelines, USCG-regulated small vessels are not subject to land-based architectural configuration requirements. Although we do our best to accommodate passengers with limited mobility consistent with our vessel capabilities, staffing and the docking space which is publicly owned and controlled, we can do a better job with advance notice .

LAZ Parking Garage at 111 E. Wacker Drive. This garage is across the street from our street-level dock entrance. Make a self-parking reservation online .

Discount rates available for Mercury customers with validation: $14 for 1-3 hours or $15 for 3-4 hours of parking. After 4 hours, standard rates apply. IMPORTANT: You must have your parking ticket stamped at our ticket window or on your boat in order to receive the discounted rate. Stamped tickets must be further validated at the parking garage office before departing the garage. Note: LAZ Parking Services at 111 E. Wacker is not owned or affiliated with Chicago’s First Lady Cruises. The parking information posted here is merely for the convenience of our guests and is not to be construed as a recommendation or endorsement.

We are located on Michigan Avenue just 3 blocks north of Millennium Park. Visit TheMagnificentMile.com or MillenniumPark.org for activities, events and special offers.

Opening for the Chicago Sailing Season: May 17th! Click to view all sails aboard Tall Ship Windy.

Tall Ship Windy

The official flagship of the city of chicago chicago skyline tours & boat excursions sailing on lake michigan from navy pier, the official flagship of the city of chicago chicago skyline sails & tours.

Initial Public Offering Announcement

AMDI plans to conduct its initial public offering (IPO) through the New York Stock Exchange American with the symbol ‘AMDI’ through its underwriter, Kingswood Investments, a division of Kingswood Capital Partners, LLC (or Kingswood), which is acting as the sole representative of the underwriters. AMDI anticipates a public offering price between $3.50 to $4.50.

AMDI is a maritime tour activity and attractions operator with the following wholly-owned operating units: Seas the Day Charters in the U.S. Virgin Islands, Tall Ship Windy in Chicago, Illinois and Paradise Adventures in Panama City Beach, Florida. The Company plans to use the proceeds of its IPO to acquire Paradise Yacht Management and Charter Smarter in the U.S. and British Virgin Islands and the Bahamas.

Interested parties may subscribe to the IPO or obtain a prospectus and more information at  Webull .

You may also obtain the Company’s prospectus and other information at the  SEC website .

Join us for Opening Weekend May 17 – May 19, 2024!

Tall Ship Windy offers an unforgettable sailing experience. Explore Chicago’s Skyline and choose from Sunset Sails, Skyline Sails and Educational Sails.

Sail in Florida and the Virgin Islands!

Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.

If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.

Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.

No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.

Paradise Adventures Catamarans and Watersports

Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!

• Experience inflatable fun on a Privateer Adventure Tour
• Snorkel and explore Shell Island
• Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
• Book a private charter on a catamaran, sailboat, powerboat or pontoon boat

Learn more about Paradise Adventures

Charter Smarter

Explore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!

• Each week-long adventure includes a professional captain, a skilled chef and all meals and drinks
• Take advantage of all your catamaran’s amenities, water toys and land-based activities in paradise
• Bring your family or friends and create memories that will last a lifetime

Learn more about Charter Smarter

Seas the Day Charters USVI

Enjoy a full or a half-day adventure with Seas the Day Charters USVI!

• Luxury sailing excursions & fast powerboat adventures
• Private & semi-private charters available
• Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
• Explore the US Virgin Islands or the British Virgin Islands

Learn more about Seas the Day Charters USVI

Chicago Skyline Sail

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

Hour Glass 75 Minutes | Starting at $39

• Hour Glass 2 Hours

Monday Night Blues Summer Concert Series

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago at sunset from the waters of Lake Michigan, accompanied by the sweet sounds of the blues.

• Hour Glass 90 Minutes

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy!

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

• Frequently Sells Out
• Hour Glass 75 Minutes

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

Chicago’s Famous Friday Night Pirates Pub Sail

Sail into the night and embark on a two-hour party sail from Navy Pier; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This popular Chicago event is one you will not want to miss; it is unlike all other boat excursions in Chicago. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights on Lake Michigan.

• Great for Children!

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.

• Every night at 5pm!

Happy Arr-our Chicago Architecture and Skyline Sail

Enjoy happy hour drink specials onboard this Navy Pier Boat Tour every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration and an Architectural Tour of Chicago from the water.

Explore Chicago Sailing Special Events

Chicago fireworks cruises, special event sails, welcome aboard tall ship windy.

Tall Ship Windy, sailing from Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative and inspiring. From our daily storytelling adventures and field trips for students to our concert sails to lively Chicago Architectural Tours, there is something for everyone. Enjoy the Chicago skyline as you sail on our tall ship!

For group boat excursions and private sailing charters, email us at [email protected] or call us at (312) 451-2700 .

Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer.

Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan.

Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy.

There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy.

Choose Tall Ship Windy For Your Special Event

Tall ship windy chicago sailing reviews.

We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!

We went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.

I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.

If you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!

Had a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!

Best view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.

The most fun tour we’ve had of Chicago. The crew is fantastic and the tour guide is hilarious. His sense of humor really sets this tour apart from the rest, while still offering interesting insights on the city’s unique skyline. Loved it.

Loved our sail! I love sunsets and this in my opinion was the best way to experience the Chicago skyline. When I return I’d love to do another tour!

Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later.

The Tall Ship Windy is a must thing to do at Navy Pier. Very friendly and funny staff and always a good time, with beautiful views of the city of Chicago.

My husband and I just did the "Pirate and Maritime Stories" tour with Tall Ship Windy and it was fabulous. A lovely cruise around the Navy Pier, while hearing some fascinating pirate history about Chicago. We highly recommend this experience for any age!

I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it! It was a gorgeous summer late afternoon and the city was just sparkling. I loved having a new view of the city. Crew excellent. My nephew helped hoist a sail. Narrator very entertaining and informative. I thought the price was great for the experience.

What a great experience! Beautiful and ever-changing views of the night skyline from the lake. When they hoisted the sails and turned off the motor, it was so peaceful. The incredible fireworks were the perfect ending to this cruise. Highly suggest!!

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Cocktail Cruise on Chicago River | City Cruises™

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The Top Romantic Things to Do in Chicago

GettyI mages-Sachin Saraswat / EyeEm

America’s third coast, home to 2.7 million people, is one of the most romantic destinations in the world. Twosomes, or singles open to chance encounters, can visit a planetarium and sip cocktails after hours, ride in a Ferris Wheel at a pier, learn how to ballroom dance, view the city lights from a twilight cruise and so much more. Colossus of the Midwest, Chicago has all the urban pleasures a couple could want. Here are the top romantic things to do in Chicago.

Flirt Above the City in a Helicopter

 Chicago Helicopter Experience

Book a Private Date Night Experience with Chicago Helicopter Experience , one of Chicago's best tours, and see the Windy City from new heights. You’ll spend time in the lounge, playing games and relaxing, while you wait for your flight to take off. Once in the air, you’ll view the Chicago skyline and lakefront while your pilot points out Willis Tower, Navy Pier, Buckingham Fountain and the Magnificent Mile. Seeing Chicago’s architecture, lit up in the night sky, is truly a romantic way to spend the evening with your partner. The Date Night Experience also includes a $100 gift certificate to be used at the stylish The Duck Inn or the newly opened Monnie Burke’s , both located in Chicago’s Pilsen neighborhood. 

Learn About Space, with a Cocktail in Hand

GettyImages- Franz-Marc Frei 

One of Chicago’s top museums, Adler Planetarium , caters to all ages and has special programming at night just for adults. The long-running Adler After Dark welcomes the 21-and-over set through its doors for evening access to shows, live entertainment and thematic events. You and your date will stroll hand-in-hand through the museum’s exhibits and galleries, watch award-winning sky shows, learn from the experts during space-themed lectures and scope out stars and planets in the Doane Observatory . Enjoy a cocktail or two, available at Café Galileo’s, and peek at Chicago’s glimmering skyline. 

Cruise the Chicago River at Twilight

TripSavvy / Anna Haines

Perfect for couples, Chicago Architecture Center’s Twilight River Cruise is both enlightening and dreamy. Board Chicago’s First Lady just as the sun sets, where you’ll meet a trained volunteer docent who will relay stories of Chicago’s past. You’ll learn about the different architecture as you float by more than 50 buildings along the Chicago River. Enjoy a snack or adult beverage from the bar and toast the night away. 

Explore a Romantic Neighborhood

 Getty Images- James Andrews

Any Chicagoan will tell you that the true heart of the city exists in the neighborhoods. Take your loved one to historic Andersonville, a lovely neighborhood on the north side with Swedish roots, a thriving network of independent businesses, some of the top restaurants and bars, and one of the city’s largest LGBTQ+ population.

Shop at Alley Cat Comics, sample one of the beers on tap at Hopleaf or Simon’s Tavern, see an other-worldly show at the Neo-Futurist Theater , be entertained at Chicago Magic Lounge and learn about gin and whiskey at KOVAL through a tour or workshop. 

Ride the Ferris Wheel at Navy Pier

 Getty Images- Michael Lee

Navy Pier’s Centennial Wheel is a fun way to see the city’s skyline and lakefront from a new viewpoint. Experience this top Chicago attraction with your loved one, sheltered from the wind inside of a gondola. Purchase a Centennial Wheel VIP Gondola Buy-Out, a luxury experience that includes a ride in a posher cabin, with nicer seating and a glass bottom, for up to four guests. If you ride at night, you can see an LED light show, blinking from the wheel’s spokes. 

Indulge in a Couples Massage

 Ritz-Carlton Chicago

One of the perks of a big city is access to luxury hotels that offer special services like couples’ massages and sedative body treatments. The Chuan Spa at The Langham Chicago, the Waldorf Astoria Spa and Health Club , the Spa at Four Seasons Hotel Chicago and the Ritz-Carlton Chicago Spa all offer extravagant treatments meant to help you relax, detox and breathe a sigh of relief. 

Watch the Sunset from a Skyscraper

 Wendy Altschuler

View the Windy City’s skyline and Lake Michigan from 360 CHICAGO in the iconic John Hancock building. Home to TILT , a moving platform that slides you out over Michigan Avenue, 360 CHICAGO is the perfect date night. Arrive at night—the last admission is at 10:30 p.m., and plan on enjoying a beer from Revolution Brewing, served at Bar 94, Chicago’s highest bar. 

Dance with a Date

 Getty Images/JackF

Connect with your partner and learn how to dance at Ballroom Dance Chicago . This 30-minute introductory private lesson is meant to be fun. You’ll work on basic movements with an instructor and then, if you’re interested in more, move on to hour-long lessons. Bring along your favorite wine, beer or beverage to make a proper date out of the experience. Group dance lessons are also offered and, if you don’t have a partner, you can still join in on the fun and meet someone new as a solo dancer. 

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Chicago River Boat Architecture Tours

Chicago River Tours | Fireworks Tours | Jazz/Cocktail Tours

River Boat Tours

Book your tour now, book by phone: (708) 488-6343, about the tours, chicago river boat architecture tours .

Welcome to Chicago River Boat Architecture Tours!  We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago.

About The Chicago River Boat Architecture Tours

Chicago is known around the world for its architectural feats, both inside and outside of the buildings. From the 100-year-old Art Deco, Neo-Classical, and Gothic Towers, to some of the tallest modern-day skyscrapers, Chicago is where old meets futuristic architectural endeavors. It has something for everyone in a way that no other city replicates today.

Why Tour Chicago’s Architecture with Us?

We are born-and-raised Chicagoans ourselves, passionate about the community that we know and love. That passion and desire spills into all of our tours, drawing on personal experiences for curating a tour that just can’t be duplicated by a book or a movie. We want you to experience everything firsthand. Why tour with us?

• Expertise: All of our tour guides are either architects, architecture students, or architecture historians, making for an in-depth and personally rooted kind of touring experience that covers all of the discreet details.
• Variety: We offer a variety of uniquely different tours that cover everyone’s individual taste. We offer the Chicago River Boat Architecture Tour that takes you down the famous Chicago River; there are several different options such as Architecture, History, Cocktail Cruises and Firework Viewing Tours
• Flexibility : We want you to enjoy your Chicago River Boat touring experience, which is why we’re happy to talk with you and learn more about how our tours can accommodate you, your party, or your corporate outing. Our tours run daily, with availability always posted on our website here.

Our Tours  

• Chicago River Boat Architecture Tour : When in Chicago, cruising down the Chicago River is  a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river.
• Chicago River Boat Cocktail Tour : Join us for this great Architecture Tour while sipping craft cocktails, beer or wine available for purchase at our bar on board!
• Lake Michigan Navy Pier Fireworks Cruise :  Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued a proclamation approving the use of fireworks to celebrate the World’s Colombian Exposition and to celebrate the nation’s 117th Independence Day. This fascination with fireworks, noise, and color continues today. The City of Chicago offers a fireworks show at Navy Pier on Saturday nights at 10:15 p.m. The Fireworks Cruise sails on both the Chicago River and Lake Michigan each Saturday at 8:30 pm.

Our Commitment to Your Touring Experience

We believe that tours should be entertaining, enlightening, informational, and perfectly organized, every single time. A tour shouldn’t feel laborious in any way; you should feel an effortless inclination to learn more about what we present at your fingertips. With our Chicago architectural tours, that’s exactly what we strive to provide, basing each tour from the perspective of an expert with the real-life example in the background.

If you’re thinking about booking a tour with us, know that our commitment to flexibility and accessible makes our Chicago Architecture Tours easy and convenient:

• 3 pm *Not Available Friday thru Sunday Summer Months*
• 6:30 pm (Jazz Band, Cocktail w/bar) *Sunday Only*
• 8 pm (Wednesdays)
• 8:30 pm (Saturdays)
• Seniors $48
• Youths $30 (7-12 years old)
• Children 6 and under Free

BOOK YOUR TOUR TODAY

Click Here to Purchase a Gift Certificate

Chicago river boat cocktail tour.

Join us in the evening to sip cocktails while cruising the historic Chicago River! Get the same tour just with a cocktail in your hand! Premium bar on board with craft cocktails, wine and beer available for purchase. Drinks may be purchased individually with a credit card on the boat. Tour Information Pricing Adults $49… Continue reading Chicago River Boat Cocktail Tour

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Chicago river boat architectural tour.

Forming a length of 156 miles when combined, the Chicago River is a system of rivers and canals the characterize the infamous skyline of Chicago today. The river, running through the city, including the city center Chicago Loop, is evident of man made design and infrastructure when completed craftily. In 1887, the river was reversed… Continue reading Chicago River Boat Architectural Tour

Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)

Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with fabulous light show, at Navy Pier. Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued… Continue reading Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)