Chicago’s water tours offer the city’s best sightseeing value, combining stunning views with rich history. The 90-minute architecture cruise stands out as the most worthwhile option, featuring expert commentary about the city’s world-famous skyline. We especially love Mercury Cruises’ sunset tours on Lake Michigan, which provide spectacular photo opportunities and a relaxed atmosphere. For families seeking excitement, Seadog’s speedboat tours deliver thrills while covering major landmarks. History buffs will appreciate the evening gangster-themed cruises, though they can be crowded in peak season. Looking for a special evening? The dinner cruises by Odyssey showcase excellent views paired with good food. Ready to explore Chicago from the water? Check out our recommended tours below.
Key Points
- Chicago offers a variety of architecturally and scenically focused boat tours, including 90-minute architectural tours, 30-minute skyline cruises, and high-speed sightseeing tours.
- Unique thematic cruises such as Lake Michigan sunset cruises, historic gangsters and ghosts cruises, and fireworks and dinner cruises provide memorable experiences.
- Combination tours and educational experiences, like the First Lady River Cruise Combo and the Chicago History & Architecture Walking Tour with Boat Cruise, offer comprehensive city exploration.
- Private and customizable experiences, including private catamaran sailing and speedboat tours, cater to personalized preferences and group needs.
- Tours generally offer knowledgeable guides, wheelchair accessibility, and high customer satisfaction, with a 95% recommendation rate.
Chicago City Tour With Architecture River Cruise Option
If you’re looking to dive into Chicago’s rich architectural heritage and iconic cityscapes, the Chicago City Tour with Architecture River Cruise is a must-do experience.
Aboard a comfortable, large-windowed minibus, you’ll explore the city’s top attractions, from the Museum Campus to the famous Buckingham Fountain. The small-group size ensures a personalized touch, and you can upgrade to include a Chicago River architecture boat tour for an immersive look at the city’s architectural history.
Knowledgeable and entertaining guides provide insightful commentary, and the flexible cancellation policy allows you to adjust your plans with ease.
With high satisfaction and a 95% recommendation rate, this tour offers an unbeatable way to discover the best of Chicago.
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Chicago River: 90-Min Architecture Boat Tour
For an unparalleled glimpse into Chicago’s renowned architectural heritage, embark on the Chicago River: 90-Minute Architecture Boat Tour. Priced at $44.00, this popular 1.5-hour cruise offers breathtaking views of the city’s iconic skyline and its groundbreaking buildings.
With a 4.8-star rating from over 5,800 reviews, this tour provides an engaging and informative experience. Cruise along the Chicago River, as a knowledgeable guide shares insights into the city’s architectural marvels.
From modern skyscrapers to historic landmarks, this tour showcases the diverse design that has defined Chicago’s landscape. Whether you’re an architecture enthusiast or a first-time visitor, this boat tour offers an unparalleled way to explore the Windy City.
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Lake Michigan Sunset Cruise in Chicago
Embark on the captivating Lake Michigan Sunset Cruise in Chicago, offering a 1.5-hour journey along the city’s iconic waterfront.
Departing from 400 N Michigan Ave, you’ll cruise past notable landmarks like the Magnificent Mile, John Hancock Building, and Willis Tower, all while enjoying scenic views of the Chicago skyline and Lake Michigan at sunset.
This cruise features indoor and outdoor seating, a climate-controlled lounge, and a full-service bar.
With over 1,200 reviews and a Badge of Excellence, this cruise is perfect for special occasions or anyone seeking a unique perspective of Chicago.
Arrive 30 minutes early, and don’t forget to book parking in advance.
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Chicago: Historic Gangsters & Ghosts Night Cruise
On the Chicago: Historic Gangsters & Ghosts Night Cruise, you’ll uncover the city’s dark underbelly and chilling tales from the past.
Embark on this 1.5-hour tour and explore the haunts of notorious mobsters like Al Capone. You’ll hear spine-tingling stories of the gangsters and ghosts that once roamed the streets.
The 4.7-rated tour provides a unique perspective on Chicago’s seedy history, immersing you in the city’s shadowy past.
Whether you’re a true crime buff or simply seeking an eerie adventure, this nighttime cruise promises an unforgettable experience.
Don’t miss the chance to explore Chicago’s haunted heritage on this highly-rated tour.
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Chicago Architecture River Cruise
Discover Chicago’s iconic skyline on the renowned Chicago Architecture River Cruise.
With 14,019 reviews and a 97% traveler recommendation, this 1-hour tour offers a unique and informative experience for first-time and time-pressed visitors.
Depart from Navy Pier or Michigan Avenue and enjoy live expert commentary on the city’s architectural milestones and notable buildings, including the Wrigley Building and John Hancock Center.
The cruise covers multiple branches of the Chicago River, showcasing designs by renowned architects like Mies van der Rohe and Helmut Jahn.
Onboard amenities include restrooms, drinks, and WiFi, making this a family-friendly and accessible option to explore Chicago’s rich architectural heritage.
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Chicago: First Lady River Cruise & Architecture Center Combo
For those looking to explore Chicago’s architectural wonders in depth, the Chicago: First Lady River Cruise & Architecture Center Combo offers an unparalleled experience.
The 1.5-hour guided architecture cruise along the Chicago River provides an up-close look at the city’s iconic skyscrapers and historic buildings, with an expert commentary on their design and significance.
Afterward, you can visit the Chicago Architecture Center, an interactive museum that delves deeper into the city’s rich architectural history.
This combo package, which starts at $44 per person, is a must for architecture enthusiasts seeking a comprehensive and immersive Chicago experience.
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Chicago River Architecture Tour With Small Boat Upgrade Option
Explore the architectural dynamism of Chicago on the Chicago River Architecture Tour with a small boat upgrade option.
Enjoy a scenic cruise along the river, taking in iconic landmarks like soaring skyscrapers, Navy Pier, and the “Bean” sculpture. With a knowledgeable local guide, you’ll learn about the architectural movements that have shaped the city.
For a more intimate experience, opt for the small boat upgrade, which accommodates a maximum of 60 people. Complimentary bottled water, coffee/tea, and snacks are provided, and alcoholic beverages are available for purchase.
The tour is wheelchair accessible and conveniently located near public transportation, making it a must-do activity for most travelers.
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Chicago: Historic Architecture Chicago River Small Boat Tour
Enjoy Chicago’s architectural splendor on the intimate Chicago: Historic Architecture Chicago River Small Boat Tour.
At just €55.87 per person, this 1.5-hour cruise showcases the city’s iconic skyline from the unique perspective of a small historic riverboat.
Enjoy complimentary Starbucks, sodas, and snacks as you listen to a live guide’s informative and engaging commentary on the architectural designs and innovations that have shaped the cityscape.
With a capacity of around 30 people, you’ll appreciate the smaller and more personalized experience over a large ship tour.
Positive reviews highlight the tour’s educational value and enjoyable atmosphere, making it a must for architecture enthusiasts visiting Chicago.
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Lake Michigan and Chicago River Architecture Cruise by Speedboat
Take a thrilling architectural tour of Chicago by speedboat on the Lake Michigan and Chicago River Architecture Cruise.
You’ll board a riverboat and cruise up the Chicago River, passing iconic landmarks like the Tribune Tower and Willis Tower. Learn about the city’s architectural history and engineering marvels as you ride through historic locks separating the river from Lake Michigan.
Then, switch to a speedboat for stunning views of the Chicago skyline, Museum Campus, Grant Park, and Buckingham Fountain.
The 75-minute tour is wheelchair accessible, though not recommended for those with certain health conditions.
With 229 positive reviews, it’s a must-do for architecture and boat enthusiasts.
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Chicago: Architecture River Cruise & Hop-on Hop-off Bus Tour
Combine the architecture river cruise and hop-on hop-off bus tour to see Chicago’s most iconic sights.
The 75-minute river cruise provides guided commentary and views of landmarks like Willis Tower, Navy Pier, and the Magnificent Mile.
The open-top bus tour offers panoramic vistas of Millennium Park, Grant Park, and the Art Institute.
Flexibility to hop on and off at leisure lets you explore must-see destinations.
While the river cruise isn’t wheelchair accessible, the tour overall earns a solid 4.4/5 rating.
Some users note scheduling issues during events, but overall find the experience interesting and entertaining.
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Lake Michigan Skyline Cruise in Chicago
The Lake Michigan Skyline Cruise offers a captivating 30-minute journey on the waters of Lake Michigan, showcasing Chicago’s iconic architecture and landmarks.
With pre-recorded commentary, you’ll learn about the city’s history and see notable buildings like the Willis Tower and Aon Center.
The cruise’s maximum capacity of 200 travelers ensures an intimate experience, and you can bring your own food and drinks or purchase them on board.
While some guests prefer live tour guides, the relaxing atmosphere and unique perspective on Chicago’s famous skyline have earned the cruise 761 reviews with an average rating of 4.5 stars.
With free cancellation up to 24 hours in advance, it’s a flexible and affordable way to explore the city by water.
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Chicago: History & Architecture Walking Tour W/ Boat Cruise
Enjoy the rich history and captivating architecture of Chicago during this 2.5-hour guided tour.
Explore iconic landmarks like the Cloud Gate, the Chicago Riverwalk, and the Magnificent Mile, stopping for optional photos along the way.
Discover the city’s unique Pedway system and savor local street food.
Culminate your experience with a 75-minute Shoreline Architecture Boat Cruise, offering breathtaking views of the city’s skyline.
With a small group size and an English-speaking guide, you’ll enjoy a personalized and convenient tour, complete with skip-the-line access.
Priced at $104 per person, this tour provides an excellent value for your money and a memorable way to experience the best of Chicago.
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Best of Chicago Small-Group Tour With Skydeck and River Cruise
Take in the best of Chicago’s iconic landmarks and architectural gems on this comprehensive small-group tour.
Explore the stunning vistas from the Willis Tower Skydeck, marvel at the iconic Bean sculpture, and stroll through Millennium Park.
Then, embark on a 1-hour 15-minute architectural river cruise showcasing over 40 landmarks.
Admire the city’s skyline from the Adler Planetarium and take in the grandeur of Buckingham Fountain.
With hotel pickup, a professional guide, and all admission fees included, this tour provides an effortless way to experience Chicago’s top highlights, especially for first-time visitors.
Just be sure to communicate clearly about the meeting point to avoid any confusion.
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Chicago: Private Catamaran Sailing for up to 12 People
Explore Chicago’s picturesque skyline from the comfort of a private catamaran. This 2-4 hour experience accommodates up to 12 people, with prices starting from $1,500.
Aboard the city’s largest chartered catamaran, you’ll enjoy a full kitchen, Yeti cooler, and Bluetooth radio. Customize your adventure with lessons, tours, or a laidback party cruise.
Groups over six must hire a qualified operator, costing $10-$11 per person per hour. Restrictions apply, so check if you or your group members are suitable.
With breathtaking views and a yacht concierge, this is the perfect way to experience Chicago from the water.
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Chicago Educational Tour and Sail Aboard a Tall Ship
Climb aboard the impressive tall ship and embark on a captivating educational tour of Chicago’s iconic waterfront.
With a maximum capacity of 148 passengers, this 4.5-star rated experience offers a family-friendly and engaging environment.
You’ll assist the crew in raising the sails while enjoying live commentary and breathtaking views of the Chicago skyline and Lake Michigan.
Though alcoholic drinks and food are available for purchase, gratuities aren’t included.
While the tour isn’t wheelchair accessible, children are welcome with adult supervision.
With a Badge of Excellence, this is a highlight of any visit to the Windy City.
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Chicago: Private Yacht Charter
For a more exclusive Chicago experience, consider chartering a private yacht.
Get a taste of the high life as you cruise along the Chicago River and take in panoramic views of the city skyline.
With a private yacht, you can customize your itinerary, whether you want to host a corporate event, enjoy a romantic dinner, or celebrate a special occasion with family and friends.
Private yacht charters typically range from 1.5 to 3 hours and can accommodate up to 6 guests.
Prices start around $500, making it an unforgettable way to experience Chicago from the water.
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Chicago Urban Adventure River and Lake Cruise
The Chicago Urban Adventure River and Lake Cruise provides an unforgettable sightseeing experience along the waterways of Chicago.
This tour showcases the city’s iconic skyscrapers and historic buildings, with live commentary offering insights into its rich history and culture.
Suitable for all ages, the cruise delivers excellent value as a great introduction for first-time visitors.
Admire the stunning skyline from unique perspectives, particularly beautiful at sunset or night.
While not wheelchair accessible, the tour is stroller friendly.
Discounted parking is available, and the maximum capacity is 115 travelers.
Reviewers praise the knowledgeable guides and recommend the evening cruises for their breathtaking views of the Chicago cityscape.
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Chicago Skyline Tall Ship Sightseeing Cruise
Experience the Chicago Skyline Tall Ship Sightseeing Cruise aboard the Windy, a 148-foot schooner that offers a unique perspective of the city’s iconic architecture and waterfront.
This 75-minute tour features live narration, restrooms, and refreshments for purchase. Choose from themed tours highlighting pirates, architecture, or sunsets, and participate in hands-on activities.
Confirmation is provided upon booking, and you’ll want to arrive 30 minutes early. While not wheelchair accessible, the experience is designed for travelers seeking a memorable view of Chicago from the water.
Dress for the weather, as sailing may be limited in high winds. Bring the family, but children under 16 must be accompanied by an adult.
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Chicago: Fireworks Cruise With Lake or River Viewing Options
Take in the dazzling fireworks display over the Chicago skyline with the Chicago: Fireworks Cruise With Lake or River Viewing Options.
Choose between a 45-minute family-friendly cruise on the Chicago River or a 2-hour cruise that takes you through the Chicago Lock System to Lake Michigan. Both offer spectacular views of Navy Pier’s fireworks, along with the city’s iconic architecture and glittering skyline.
Enjoy the cruise’s full-service cash bar and locally sourced food and drinks. Children under 4 go free.
Though reviews are mixed on the cruise length and firework views, it’s a unique way to experience Chicago’s famous Fourth of July celebrations.
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Chicago Private Sunset Sail on Lake Michigan
Set out on a private sunset sail on Lake Michigan with the Chicago Private Sunset Sail, a 2-hour charter that showcases the city’s magnificent skyline.
Led by a US Coast Guard-certified captain, you’ll enjoy a customizable experience – choose your music, route, and bring up to five guests.
Admire the stunning views of the Chicago skyline and Lake Michigan while sipping your favorite beverages.
The tour includes Bluetooth speakers, all taxes and gratuities, and the option to bring your own food and drinks.
With 24 reviews and a 100% traveler recommendation, this is a must-try experience for any visitor to Chicago.
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Chicago: Fireworks Buffet Dinner Cruise on Lake Michigan
Enjoy a captivating evening of food, entertainment, and breathtaking views on the Chicago Fireworks Buffet Dinner Cruise on Lake Michigan.
This 3-hour cruise offers a multi-course dinner buffet, live DJ entertainment, and unbeatable views of the Navy Pier fireworks display. Enjoy scenic views of Chicago’s iconic skyline as you dine on a variety of salads, entrees, and desserts.
Dress in dressy-casual attire and explore the open-air rooftop decks. While the fireworks display is weather-dependent, this cruise promises a memorable experience celebrating special occasions.
Depart from Navy Pier and prepare for an evening of lakefront wonder.
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Chicago Fireworks Dinner Cruise With Buffet
The Chicago Fireworks Dinner Cruise with Buffet offers a unique and captivating evening on the waters of Lake Michigan. Departing from Navy Pier, you’ll enjoy stunning views of the Chicago skyline at sunset.
The buffet dinner, drinks, and live entertainment create a celebratory atmosphere, perfect for birthdays, anniversaries, or any special occasion. While the food quality has received mixed reviews, the fireworks display and overall ambiance are highlights.
Keep in mind that the cruise has a maximum of 15 travelers and may not be wheelchair accessible. With its lively music, breathtaking vistas, and the chance to witness a fireworks show, this cruise provides a memorable night out on the water.
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Chicago: 1.5-Hour Scenic Sunset Lake Cruise
Hop aboard the Chicago: 1.5-Hour Scenic Sunset Lake Cruise and witness the city’s skyline bathed in the warm glow of the setting sun.
You’ll cruise through the Chicago River and Lake Michigan, taking in the views from the outdoor deck or indoor climate-controlled seating.
Enjoy live commentary from a local guide and indulge in local beer, spirits, and Garrett’s Popcorn from the full-service cash bar.
With free cancellation up to 24 hours in advance and the option to reserve now and pay later, it’s the perfect way to experience Chicago’s waterfront.
Don’t miss the chance to capture the breathtaking sunset over the city.
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Chicago Shoreline Adventure Boat Tour
For a high-speed sightseeing adventure along Chicago’s iconic skyline, consider the Chicago Shoreline Adventure Boat Tour. This 36-reviewed, 100% recommended tour offers an adrenaline-filled experience showcasing the city’s top landmarks, including Museum Campus, Navy Pier, and Millennium Park.
Operated in a small-group setting with a maximum of 6 travelers, the tour provides exceptional views from the water. With various departure times, it’s convenient to fit into your schedule.
However, it’s not recommended for those with back problems, pregnant travelers, or those with serious medical conditions.
At ₹7,810.13 per person, this tour is covered by a lowest price guarantee, making it an excellent value for your Chicago sightseeing experience.
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Chicago: Lake Michigan Skyline Cruise
On Navy Pier, embark on the Chicago: Lake Michigan Skyline Cruise to enjoy a 30-minute journey along the iconic lakefront.
This budget-friendly cruise costs just $37.57 per person and offers panoramic views of the Chicago skyline and landmarks like the Willis Tower.
You’ll sail north and south on Lake Michigan while listening to engaging commentary. Snap photos at the photo stop, and don’t miss the boarding photo available for purchase.
With a 4.6/5 rating from over 700 reviews, this cruise delivers excellent value.
Avoid bringing food, drinks, or electric wheelchairs. If you need to change your booking, expect a $10 fee per ticket.
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The Sum Up
Whether you’re interested in architecture, history, or simply taking in the stunning skyline, Chicago’s boat tours and cruises offer something for all. With a variety of options to choose from, you’re sure to find the perfect way to explore the city’s waterways and create lasting memories. Don’t miss the chance to experience the Windy City from a unique perspective.