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Architecture Tour

TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour.

There’s one sure recipe to make your business or social event even more memorable – just add water and Chicago’s First Lady!

Recalling the handsome elegance of 20th century luxury yachts, our vessels are sure to make an impression. Choose from seven perfectly sized ships for your private event.

Your wedding is the start of your lifelong journey together, so begin that journey in a truly memorable way - a wedding cruise down the Chicago River.

Evening River Cruise

Experience our renowned daytime CAC River Cruise in the glow of the setting sun. Take in the city’s magnificent architecture bathed in golden light as it begins its transition from day to night.

chicago skyline yacht cruise

“The very best city tour I have been on in my life! We were in America for a month and this was our best morning.” - JurassicBill TripAdvisor, Dorset UK

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A Memorable Mother's Day in Chicago

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"What an amazing experience, this tour brings all the beautiful architecture and history to life.” - Rachel M Yelp, Arizona, USA

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Tall Ship Windy

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Chicago Skyline Sail Aboard 148' Tall Ship Windy

Quick Details

  • Hour Glass Duration: 75 Minutes
  • User Ages: All Ages
  • Calendar Availability: Daily
  • Sailboat Sail: Skyline Cruise Chicago
  • Map Marker Departure: Chicago's Navy Pier

Experience breathtaking views of Chicago from the waters of Lake Michigan! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores and skyline with a leisurely trip around Lake Michigan.

There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship! Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.

Experience The Beautiful Chicago Lakefront With Three Sailing Options

Tall Ship Windy offers three exciting ways to enjoy the Chicago lakefront and skyline. Learn more about our Skyline sails and book today!

1pm. Pirates and Maritime Stories

Join us on our main deck for “True Stories of Piracy” on the Great Lakes and the Caribbean! From epic battles to trickery and treasure, experience the incredible tales of real pirate adventure that happened right here on these magnificent inland seas. This Chicago sail is both educational and entertaining!

On this unforgettable sail, you will also enjoy awe-inspiring views of the world-famous skyline of the Windy City while sailing the gentle waters of Lake Michigan. There’s something for everyone on this fun tour.

Participants and guides on an educational sailing tour in Chicago

3pm & 5pm. Architecture and Skyline Sails

Experience breathtaking views of Chicago from the water! Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. The 3pm and 5pm tours feature the history of Chicago and its world-famous architecture. To learn about the people, plans and persistence that shaped Chicago’s most famous sights join us on the main deck and enjoy the lively and educational narration.

5PM: Happy Arr-our Chicago Skyline Sail

Enjoy onboard happy hour drink specials every night at 5pm! All ages welcome. Happy hour specials for guests 21+, with valid ID.

  • Chevron down Beginning September 3: Enjoy a Sunset Skyline Sail at 5pm and a Late Summer Twilight Sail at 7pm

Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.

chicago skyline yacht cruise

7pm. Sunset and Skyline Sail

Head out on our traditional tall ship and explore the majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world-famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline. A perfect Sunset Skyline Sail for individuals, family and friends.

On our Twilight Sail, enjoy the beautiful colors splashed across the post-sunset sky. You’ll enjoy an evening sail on Lake Michigan aboard Tall Ship Windy and take in the world-famous Chicago skyline as day transitions to night.

Chicago skyline at sunset

  • Chevron down Board First with VIP Captains Boarding - Limited Tickets Available!

All seating on board Tall Ship Windy is first come, first served. Guests with  VIP Captains Boarding  tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.

All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

  • Chevron down Add-on Trip Insurance

$8.00 Per Guest | Add to your ticket at checkout

Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.

General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

  • Chevron down Cancellation Policy
  • RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
  • No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
  • The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
  • Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.

Become a Skyline Sails Member!

Related sails.

  • 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.

  • 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.

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chicago skyline yacht cruise

Chicago Boat Charters

Live Your Best Boat Life in Chitown

The perfect day on the water is always on a luxurious yacht or boat. Explore them all and find the best option for your upcoming boat rental. We promise it'll be an unforgettable experience on the water.

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chicago skyline yacht cruise

Chitown Boating

Chicago’s Newest Marketplace for boat rentals, skyline cruises, river cruises, yacht charters, and playpen charters! Miami, San Diego, Cancun, Puerto Vallarta, and Cabo boat rentals also available.

chicago skyline yacht cruise

Rent a Luxurious Yacht or Boat

We promise it'll be an unforgettable experience on the water.

Boating Experiences

We offer several unique and memorable experiences on the lake whether you want to enjoy the beautiful Chicago skyline, or party in the playpen.

chicago skyline yacht cruise

Monroe Harbor

Anchor at Monroe Harbor with a great 360 view of High-Rise buildings, Buckingham Fountain, Grant Park, Navy Pier, and Lake Michigan.

chicago skyline yacht cruise

Hang out at the Chicago Playpen where all the boats anchor and party it up.

chicago skyline yacht cruise

River Cruise

See some of the greatest architecture with the High-Rise buildings in Downtown Chicago with a River Cruise.

chicago skyline yacht cruise

Night Cruise

See a beautiful Chicago Skyline with the amazing High-Rise buildings lit up at night.

chicago skyline yacht cruise

Sunset Cruise

See an amazing sunset overlooking the Chicago Skyline from Lake Michigan.

chicago skyline yacht cruise

Skyline Cruise

See the beautiful Chicago Skyline from Lake Michigan with a Skyline Cruise.

chicago skyline yacht cruise

Fireworks Cruise

See the Fireworks on Lake Michigan on a Wednesday or Saturday night. 

The skyline views were breathtaking and the music was perfect for the occasion. The party on the boat was even better than I expected. I highly recommend Chitown Boating for your next yacht rental!

chicago skyline yacht cruise

The views were amazing and it was the perfect setting for a dinner with friends. It was so relaxing and we all had a great time. I would highly recommend Chitown Boating for anyone looking for a memorable experience on the water.

chicago skyline yacht cruise

Special Events

Are you looking for a unique venue to celebrate something special? If so, we have the right boat for you. We have some phenomenal boats for any occasion.

chicago skyline yacht cruise

Engagements

chicago skyline yacht cruise

Bachelorette Parties

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Corporate Events

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Anniversaries

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I Just Want To Party On A Boat

Our boating partners.

Chitown Boating has partnerships with yacht owners in vacation destinations like Cancun, Cabo San Lucas, Miami, Puerto Vallarta, and San Diego.

chicago skyline yacht cruise

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chicago skyline yacht cruise

Chicago’s Newest Marketplace for boat rentals! Cancun, Cabo San Lucas, Miami, Puerto Vallarta, and San Diego boat rentals also available.

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Mercury, Chicago's Skyline Cruiseline

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Chicago Urban Adventure River and Lake Cruise

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Chicago 3D Fireworks Cruise

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Chicago by Night: 90 Minute River and Lakefront Cruise

chicago skyline yacht cruise

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

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Mercury, Chicago's Skyline Cruiseline - All You Need to Know BEFORE You Go (2024)

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Get the perfect introduction to Chicago and its history on this 40-minute panoramic Lake Michigan tour!

  • Hop on board and see Chicago's striking skyline from Lake Michigan.
  • The 40-minute tour will take you past Chicago’s world-famous landmarks.
  • Enjoy close-up views of iconic buildings and make use of the photo ops.
  • Listen to the commentary on board and discover why Chicago is considered to be the home of modern American architecture.
  • Cruise ticket
  • Live commentary
  • Food and drinks

Cancellation policy

These tickets can't be cancelled or rescheduled.

Ratings & Reviews

Your experience.

Without a doubt, Chicago's skyline is beautiful from every angle - whether you're in a cab, on a sidewalk, or traveling through the train. But one of the best ways to soak in all of the amazing architecture in the city is through a boat tour on the river. Hop aboard this cruise and get a peek at the city's stunning skyline in just 40 minutes. You will be departing from Navy Pier and cruising along the coastline of one of the Great Lakes. Simply sit back, enjoy the commentary on board, and take in views of the skyline from Lake Michigan. This tour is ideal for both locals as well as first-time Chicago visitors.

Know Before You Go

Discounted tickets.

Infants aged 0-2yrs can go for free. Children aged 3-12yrs enjoy reduced ticket pricing (carry a valid photo ID).

  • Your voucher will be emailed to you shortly.
  • Please display your mobile voucher along with a valid photo ID at the boarding point.
  • If you have purchased reduced-price tickets, please carry your valid photo ID proof for verification.
  • Kindly ensure that you arrive 10-15 minutes before the start time of your tour to avoid any delays.

Boarding Point

  • Redeem your ticket at Shoreline Boat Tours.
  • Address: 600 E Grand Ave, Chicago, IL 60611, United States. Get Directions to the Boarding Point

This ticket is valid for the date and time selected during checkout.

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Tour the Windy City from the water

See the skyscrapers, hear the history, and take a tour of the incredible city of chicago with shoreline sightseeing., take a tour.

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Architecture River Tour

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Michigan Avenue

401 N. Michigan Ave

Please select Navy Pier. (Skyline Lake Tours are unavailable from Michigan Avenue.)

Navy Pier

600 E. Grand Ave

124 N. Streeter Drive

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Photo of Shoreline Sightseeing boat on the Chicago River

Architecture River Tour

View over 40 Chicago landmarks on our Architecture Tour as you listen to our expert guides tell you how Chicago’s buildings and engineering made the city famous.

Overhead view of Navy Pier

Skyline Lake Cruise

See the city of Chicago as you’ve never seen it before on our classic Lake Michigan boat tour that leaves from Navy Pier and offers majestic skyline views.

Navy Pier Fireworks show, with Navy Pier at night in the foreground

Fireworks Cruise

Throughout the summer months, enjoy the Navy Pier’s spectacular Firework’s show from the water with Shoreline. Tours depart every Wednesday and Saturday evening from Memorial Day to Labor Day.

chicago skyline yacht cruise

Sightseeing in Chicago? Chicago CityPass saves 48% on premier admission tickets  to Chicago’s top 5 attractions, including the Architecture River Tour.

The reviews are in

Now in its 83rd season, Shoreline Sightseeing operates Chicago's largest and most diverse fleet of cruise boats and water taxis with 11 major tour vessels and 7 water taxis.

(312) 222-9328 ext. 1 [email protected]

  • Architecture River Tour
  • Skyline Tour
  • Fireworks Tour
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Free Spirit Yacht Cruises

Free Spirit Private Yacht Charters

Experience all-inclusive luxury and set sail across the crystal blue waters of lake michigan., lake michigan, chicago, il, welcome aboard, whether celebrating a birthday or entertaining corporate clients, we personalize every detail of your event to provide an extraordinary experience you’ll never forget. soak in the magic of the chicago skyline. sip on refreshing cocktails and indulge in an array of delicious food. we’re thrilled to have you on board.

  • Free Spirit

Our spacious Free Spirit luxury yacht accommodates up to 120 people and is custom-designed for your relaxation and comfort, inside and out. Free Spirit is perfect for larger groups for business meetings, company outings, networking events, family celebrations, weddings or parties. Whatever the occasion, it’s more memorable when it’s a boat!

  • Gypsy Spirit

Our Gypsy Spirit luxury charter yacht is perfect for an intimate gathering or a small company outing. The Gypsy accommodates up to 49 passengers, offering multi-level entertaining with a salon, galley, and aft deck lounge area. Sit back, relax and cruise Chicago River or Lake Michigan.

WHAT WE Offer

chicago skyline yacht cruise

We make special occasions memorable!

At Free Spirit Yacht Cruise, we go above and beyond to guarantee your occasion is truly special. You can delight out-of-state visitors with breathtaking views of Chicago’s world-famous skyline. Host a casual breakfast cruise with sparkling mimosas.

Need to impress new business clients? Break out of the ordinary and stun clients with an elegant dinner on a cruise along Lake Michigan.

From our attentive staff to the luxurious ambiance, our gorgeous yachts offer the perfect venue for you to host your next event.

chicago skyline yacht cruise

Ready to Start Planning Your Event?

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Free Spirit Yacht Cruises

708-361-2220

[email protected]

Burnham Harbor, Chicago, IL

Interested in chartering a yacht with us? Contact Free Spirit Cruises at 708-361-2220 or complete our online form. Let’s see how we can help you today!

Have A Question? Contact Us Today!

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Cruise the Skyline with Spirit of Chicago

Spirit of Chicago

Skyline views, delicious menus, and celebration awaits.

Spirit of Chicago is ready to show you the city.

Eat, drink, dance and take in the incredible skyline with a lunch, dinner or specialty cruise. You’ll love the Spirit menu featuring a variety of culturally-inspired recipes incorporating fresh, organic ingredients. From dinners for two to corporate outings, Spirit is fun for all. Let’s celebrate!

Nothing on land compares:

  • A rooftop lounge on the top deck
  • Three climate-controlled interior decks with panoramic windows
  • New menus with vegetarian and gluten-free options
  • Live DJ, spacious dance floors and full service bars

Call 1-888-957-2634 or visit Spirit of Chicago on the web at www.spiritcruises.com/chicago .

Facebook.com/SpiritofChicago | @SpiritNavyPier | #SpiritofChicago

Receive a 15% discount on Spirit of Chicago Lunch and Dinner Cruises.* Use promo code: NPCRUISES15 . Click here to book. *Sunday – Friday only. Does not include specialty, holiday or firework cruises. Only one discount valid per order. Offer valid on groups under 20 guests.

Spirit of Chicago Cruises

City Cruises – Spirit of Chicago Brunch Cruises

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 – Spirit of Chicago Group Cruises

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 – Spirit of Chicago Dinner Cruise

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...

chicago skyline yacht cruise

ON A BOAT SAILING

Private sailboat charters in chicago, what makes  on a boat sailing different, we're a one boat, one captain operation sharing our passion for sailing with our customers. our chicago sailboat charters & cruises have been enjoyed by thousands of guests since our first private charter in 2018. as we enter our 6th season, we pride ourselves on offering a safe & unforgettable way to experience lake michigan..

chicago skyline yacht cruise

Captain Greg & 1st Mate Cait

Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. sit back & relax as you take in the sights & sounds of chicago's famous lakefront., 2003 jeanneau sun odyssey 37, s/v dragonfly was built for day cruises & entertaining. our 37' luxury sailboat is a fantastic venue for any special occasion. we are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the us coast guard..

chicago skyline yacht cruise

Learn more about the crew & S/V Dragonfly here .

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Offering unmatched Chicago sailing charters & cruises designed to provide an adventurous escape from summer days in the city.

Our focus is on curated experiences for small groups up to 10 passengers that prefer the flexibility of a private sailboat rental. open bookings are wednesday, friday, saturday & sunday from memorial day weekend to mid-october with multiple departures daily from monroe harbor. please visit our all charters page to learn more about our special sailing adventures. chicago is the best place to combine the thrill of sailing with views of a world class skyline. simply s it back & relax as you take in the sights & sounds of chicago's famous lakefront. cheers captain greg & first mate cait.

chicago skyline yacht cruise

OVER 400 PRIVATE CHARTERS IN CHICAGO SINCE 2018

Chicago lakefront cruise.

USCG Captain 

Up to 10 Guests

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience Chicago - this is the cruise for you.

Starting at $899 for 6 guests

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Skyline Sunset Cruise

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.

Starting at $899 for 6 guests 

Sail & Swim Half-Day Charter

USCG Captain

Chicago's famous lakefront party is back. This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

Starting at $1,099 for 6 guests 

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Navy Pier Fireworks Cruise

This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.

Starting at $799 for 6 guests 

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“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!

Dyna, Chicago, IL

PLAN YOUR CHICAGO SAILING ADVENTURE TODAY!

Enjoy world-class sailing, Great Lakes swimming & luxury amenities while you're with us.

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STEP ABOARD Be first for private sailing offers & special event  happenings on Chicago's famous Lakefront.  

Welcome to the crew!

Mercury Skyline Cruise Line

Mercury Skyline Cruise Line

Best Chicago Sightseeing By Boat

Cruise your way through the turgid waters to explore the range of features of nature around us.

Tall ship windy.

The exciting boat tours have creative, inspiring, and educational elements to keep the people entertained.

River Cruise

Calm waters set you afloat on an incredible experience to take you for the best journey to nature’s nest.

Speedboat Tour

The classic speedboat journey through the waters takes you through blissful elements of a quick view of the magnificence.

Classic Lake Tour

Every mystic experience is worth savoring for the beauty and elegance the world holds in all corners.

Boat Boasts Climate-Controlled Seating Areas

Choose the seat that gives you the optimal view of the skyline that encompasses every soul on the boat.

chicago skyline yacht cruise

City Experiences

Capture every moment in the city as you take a tour by the coastline and the docks of the exotic locations.

chicago skyline yacht cruise

Shoreline Sightseeing

Choose the package that serves well for your tastes, providing you with the right escape from real-life stresses.

chicago skyline yacht cruise

Architecture Tours

If you are a lover of architecture, select a variety of options to explore the beauty of the city while floating in paradise.

Best Boat Tours To Try

Some of the highest quality luxury services in the world are available as you ride towards the horizon for a divine experience.

Seadog Lakefront Speedboat

River dinner cruise, lunch cruise, watching the sunset against the skyline.

Keep an eye on the sun to see it go up and down to mark the day’s adventures for every visitor in the city.

Cruises & Boat Tours In Chicago

chicago skyline yacht cruise

Ultimate Chicago Experience

We provide you with an extensive range of packages and features to choose from for your ultimate boating through tranquility.

chicago skyline yacht cruise

Chicago Boat Tours

Explore the city’s beauty as you take a relaxed tour in the waterways that run through every beautiful street.

Latest From Our Blog

The top 10 chicago boat cruises, sailing & water tours.

The Top 10 Chicago Boat Cruises, Sailing & Water Tours

Chicago is a popular tourist destination for a reason. It has beautiful architecture, amazing food, and great museums filled with sophisticated artworks. If you are planning on visiting Chicago as…

Five Top River Sightseeing Tour in Chicago

Five Top River Sightseeing Tour in Chicago

Chicago’s boat tours are as famous as the city itself. Tourists can enjoy seeing skyline view from few spots at the river and Lake Michigan. These tours come with guides…

Explore Chicago’s Landmarks by Boat Tours

Explore Chicago’s Landmarks by Boat Tours

The City of Chicago is the third-largest city in the United States of America. It was recognised as a city in the year 1837. The city was rebuilt after the…

Bask in the Sun in Chicago’s Boat Tour

Bask in the Sun in Chicago’s Boat Tour

Chicago is one of the vibrant cities that sits on the banks of Lake Michigan in Illinois, USA. The city is always found on the list of people looking for…

14 Best Chicago Boat Tours to Try in 2021

14 Best Chicago Boat Tours to Try in 2021

Chicago is famous for its architectural marvels, wonderful culture, food and its love for art. It is a very historically rich city with plenty of tourist attractions. Most tourists enjoy…

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THE MOST LUXURIOUS

Yachting experience.

reserve your yacht charter today

We are taking reservations for this summer and are looking forward to hosting your party! Before each charter, the yacht is thoroughly cleaned and disinfected including all surfaces, doorknobs, railings, handles, counters, tables, seating, sinks, toilets, etc. We’ve always taken safety very seriously and will continue to do so. 

In order to fulfill dreams, we strive to create the best yacht charter experience. Experience breathtaking views of the Chicago Skyline while aboard our opulent yacht. You are more than welcome to bring your own food, beverages, and anything else you may need! 

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Our larger vessel Eclipse offers four spacious entertainment areas that are available to guests onboard, perfect for celebrations, corporate outings, and more. A complimentary cooler is provided to store your ice and beverages. The vessel comes equipped with a roll-out lake pad for water activities.

Our vessel Escape is the perfect yacht to enjoy a day on the lake with friends and families. If you are looking for a more scenic experience, we can cruise down the Chicago River. A complimentary cooler is provided to store your ice and beverages. The vessel comes equipped with a roll-out lake pad for water activities.

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Searching for elite yacht charters in Chicago? Look no further because Exclusive Charter Yacht provides the greatest rental experience for a variety of occasions, including birthdays, bachelorette/bachelor parties, social gatherings, proposals, and business events. Fuel, tax, cleaning, safety instruction, and all other amenities are included in our price. We also offer a list of qualified captains who have experience with our boats. Our commitment lies in offering safe, fun, and full-service yacht charters.

There are two distinct boat options available from Exclusive Charter Yacht, each tailored to suit various preferences and price ranges. 

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Corporate Event

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Fireworks Cruise

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Birthday Party

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If you are looking for a luxury yacht that is sure to impress for corporate event, then book a business cruise on the Eclipse! Show your employees and clients that you care about their efforts and business.

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Host your Bachelor & Bachelorette parties aboard our luxurious fleet. Make this an experience you’ll never forget!

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Exclusive Charter Yacht is perfect for celebrations of all kinds. Whether you are celebrating a birthday, anniversary, or any special occasion, contact us for more information.

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Visiting Chicago? Tour the Chicago skyline over the lake day or night and experience the beauty of Chicago during the summer. 

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Have you opened a new location, redesigned your shop, or added a new product or service? Don’t keep it to yourself, let folks know.

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Experience amazing sunset cruises and firework cruises on Lake Michigan. There are numerous dates available for your own private fireworks cruise, with fireworks displays happening every Wednesday & Saturday night!

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chicago skyline yacht cruise

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

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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.

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“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

Julie G.,

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, Chicago By Night! and 3D Fireworks 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.

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.

chicago skyline yacht cruise

Youngest captain with Chicago’s First Lady Cruises is anchored by her love of the job

T he last time we saw Diamond Gibbs , then a mother of one and a senior deckhand on the Mercury Skyline Queen, she was keeping an eye on the water to make sure her passengers and other boaters on the Chicago River were safe while enjoying themselves. That was in the fall of 2019.

These days, the West Garfield Park native is at the helm of the boats that are part of Chicago’s First Lady Cruises fleet as the company’s youngest boat captain at age 26.

Gibbs, now a mother of two boys, Kameron, 9, and Zion, 2, has been rocking the four bars on her epaulets, signifying her role as captain, since August 2023. The CFL family welcomed her promotion and growth by inviting her onto one of their vessels and, as Gibbs recalls, 10 people were standing in a circle in the salon waiting for her.

“I’m thinking: What did I do? As I walked up on the boat, I was going to back on out, but I saw the owner, Captain Tim Agra standing there. I was like I can’t back out now,” she says laughing, thinking back to the day.

The group was there to congratulate Gibbs on passing the captain’s course. She said she almost teared up, but kept it together.

“I still wake up every day saying, ‘Yeah, I’m a captain!’,” she said. “Officially having the keys to the vessel, it’s nice. Being a part of the captains meeting is like, ‘I’m there! I finally made it!”

Gibbs navigates the official Chicago Architecture Center River Cruise down all three branches of the Chicago River. Five years ago, her eyes were on the prize of being a captain. Now that she has her captain’s license, she’s working toward getting the keys to all of the cruise company’s vessels, five more to be exact.

And while she’s working toward that, she’s also trying to bring more people of color and more women into the world of boating — people like Attia Gray, a Hammond resident who was serving aboard the vessel with Gibbs as first mate on a sunny April afternoon.

“I actually never did a river cruise before applying here,” Gray said. “But I just feel like the way that these boats look, the care they take, it looked like the best company to choose.”

Gray started on the recreational side of boating before transitioning to the commercial side. She already has her captain’s license, which according to Gibbs, requires the holder to have hundreds of hours and days working on the water. And that’s aside from going to school. The schools have varying requirements to get a license.

Once a captain’s license is obtained, one joins a commercial boating company, which has its own program that pairs potential captains with current captains to train them on how to run a particular ship. Both women agree it’s a process that takes time, and Gray is waiting for a spot to open up in the cruise line’s program. Gibbs said she is one of two female captains, out of 18 total captains, with Chicago’s First Lady Cruises. Gibbs can hardly wait to welcome Gray into the fold to make it a trio.

“Another female Black captain … I’ve been trying to help her get to the same level I’m on,” Gibbs said.

As members of the Ship Masters’ Association, Gibbs and Gray are doing community outreach to get more diversity on the water. Gibbs said she’s reaching out to high schools, clubs and youth groups to recruit more people.

Maritime life found Gibbs when, after a year at Malcolm X College, she was studying to be an emergency medical technician. She needed a job that allowed her flexibility with her young son. When she applied for a job with the cruise line, company officials saw on her resume that she was CPR certified and said, “Instead of working on the docks, how about giving it a try on the boat?” The rest is history. Gibbs has been with the company since 2017.

Gibbs still can’t swim, but she can stay afloat and tread water. She’s contemplating taking swim lessons with her sons. Days before Mother’s Day, Gibbs said juggling motherhood with her full-time job is a bit tough, but she said she wouldn’t have been able to do it without the assistance of her mother and the understanding and support of her colleagues in the company.

“They understand my situation. … I’m still a mom, so I have to be able to take care of the boys and help the company as much as I can,” she said. “Working here is pretty much like my second home. When I’m not at home, I prefer to be at work. I don’t even want to go anywhere else.”

Ninety-minute cruises explore both the lake and the river, and passengers hear information about Chicago’s buildings and history from tour guides. Official architecture tours, on the river only, with volunteer docents from the Chicago Architecture Center are also 90 minutes.

“As the senior female in our fourth-generation family-owned business, I am so proud of the hard work and dedication Diamond invested to become a U.S. Coast Guard licensed captain aboard our ships,” said Holly Agra, executive chairman of Chicago’s First Lady Cruises. “Her commitment to safety first, coupled with her ability to work together with fellow crew members, docents and passengers, demonstrate qualities we celebrate as a company.”

Chicago’s First Lady’s season begins in early spring and ends in November. The year-round, full-time job also entails maintaining the boats in the Dolton shipyard during the offseason. Gibbs is on the team that ensures the wood on the boats is maintained.

Gibbs has made a home for herself on the water, so much so that she’s had offers from other companies enticing her to leave CFL. But Gibbs stands firm.

“I’m very happy where I’m at,” she said.

©2024 Chicago Tribune. Visit chicagotribune.com. Distributed by Tribune Content Agency, LLC.

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Youngest captain with Chicago’s First Lady Cruises is anchored by her love of the job

chicago skyline yacht cruise

The last time we saw Diamond Gibbs, then a mother of one and a senior deckhand on the Mercury Skyline Queen, she was keeping an eye on the water to make sure her passengers and other boaters on the Chicago River were safe while enjoying themselves. That was in the fall of 2019. These days, the West Garfield Park native is at the helm of the boats that are part of Chicago’s First Lady Cruises fleet as the company’s youngest boat captain at age 26. Gibbs, now a mother of...

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  19. Youngest captain with Chicago's First Lady Cruises is anchored ...

    Diamond Gibbs, the youngest boat captain for Chicago's First Lady Cruises, pilots the Chicago Architecture Center River Cruise down the Chicago River on April 30, 2024.

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    That was in the fall of 2019. These days, the West Garfield Park native is at the helm of the boats that are part of Chicago's First Lady Cruises fleet as the company's youngest boat captain at age 26. Gibbs, now a mother of...