Chicago’s waterways offer the best possible views of its famous skyline and architectural wonders. The most worthwhile option is the classic 45-minute architecture cruise, which glides past 50+ landmarks while expert guides share fascinating stories about the city’s development. I especially love the late afternoon tours – you’ll get perfect lighting for photos and shorter lines.
For a special treat, book the 1.5-hour sunset cruise with drinks included. The commentary is excellent, and watching the city lights come alive is magical. Small-group tours provide a more intimate experience, though they tend to cost more.
To beat summer crowds, opt for a morning cruise, particularly on weekdays. Booking ahead is essential during peak season (June-August).
Our detailed guide lists the top-rated boat tours that make the most of your time and money in Chicago.
Key Points
- Chicago offers a variety of architecture-focused river cruises, ranging from 45-minute condensed tours to 1.5-hour guided cruises with expert commentary and stunning landmark views.
- Scenic and sunset cruises on Lake Michigan provide opportunities to admire the city skyline and natural beauty, with amenities like climate-controlled lounges and full-service bars.
- High-speed speedboat tours offer a thrilling perspective on Chicago’s architectural history and modern engineering, with routes showcasing landmarks along the lakefront and river.
- Small-group and private tour options provide personalized experiences, with hotel pickup, air-conditioned transport, and flexibility to visit key attractions like the Willis Tower Skydeck.
- Unique thematic cruises, such as the Chicago Fireworks Cruise and Tall Ship experiences, offer distinctive ways to explore the city’s waterways and landmarks.
Chicago Architecture River Cruise
The Chicago Architecture River Cruise offers visitors a scenic and informative tour of the city’s iconic landmarks along the branches of the Chicago River.
With over 14,000 reviews and a 97% recommendation rate, this 60-minute cruise is ideal for first-time visitors and those with limited time.
Guided by expert commentators, the tour highlights the architectural history of Chicago, including the significance of balloon-frame construction and the impact of the Great Fire of 1871.
Passengers can admire notable buildings such as the Wrigley Building, John Hancock Center, and Willis Tower while enjoying onboard amenities like live commentary, restrooms, and a pet-friendly environment.
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Chicago: 45-Minute Family-Friendly Architecture River Cruise
For those seeking a more family-friendly and condensed version of the popular Chicago Architecture River Cruise, the 45-Minute Family-Friendly Architecture River Cruise offers a delightful alternative.
Priced from $28 per person, this 45-minute cruise navigates the Chicago River, providing a unique perspective of the city’s impressive architecture.
With live commentary in English, guests can learn about the history and architects behind the iconic skyline.
Featuring indoor and outdoor deck access, a full-service cash bar, and open-air seating, the cruise offers a relaxing sightseeing experience.
Reviewers praise the knowledgeable guides and the overall enjoyable experience, making this tour a must-do activity for families visiting Chicago.
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Lake Michigan Sunset Cruise in Chicago
Offering a breathtaking perspective of Chicago’s iconic skyline, the Lake Michigan Sunset Cruise invites visitors to experience the city’s stunning architecture and natural beauty from the tranquil waters.
With over 1,200 reviews and a Badge of Excellence, this 1.5-hour cruise showcases landmarks like the Chicago River, Magnificent Mile, and Willis Tower.
Featuring an enclosed climate-controlled lounge, indoor and outdoor seating, and a full-service bar, the cruise provides a relaxed atmosphere for travelers.
Attracting a maximum of 300 guests, the sunset tour earns praise for its beautiful views, excellent sunset, and informative guide, making it an ideal choice for special occasions and photo opportunities.
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Chicago: Architecture Boat Tour With Drinks
Chicago’s architectural heritage comes alive on the Chicago: Architecture Boat Tour With Drinks.
The 1.5-hour guided cruise along the Chicago River offers an immersive experience, sailing past iconic landmarks like the Willis Tower and Wrigley Building. Knowledgeable guides share insights into the city’s architectural styles and history, while guests enjoy complimentary drinks.
With an overall rating of 4.7/5 from 335 reviews, the tour is a hit among travelers, who praise the engaging guides and educational experience.
Accessibility features, including wheelchair access and comfortable seating, make the tour inclusive.
Starting from Kč 927 per person, the tour can be booked with free cancellation or a reserve now, pay later option.
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Chicago River Architecture Tour With Small Boat Upgrade Option
The Chicago River Architecture Tour With Small Boat Upgrade Option provides an immersive exploration of the city’s architectural marvels.
Travelers can opt for a small boat tour, accommodating up to 60 people, offering unobstructed views. The tour includes landmarks like skyscrapers, Navy Pier, and the iconic “Bean” sculpture.
Guides share insights into Chicago’s history and architectural movements, catering to enthusiasts. The tour is wheelchair accessible, making it suitable for various age groups.
With 817 reviews and a 5.0 rating, the experience is highly recommended, though some note limited visibility on larger boats.
Priced at $49 per person, the tour offers a lowest price guarantee and flexible booking options.
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Chicago: Lake Michigan Skyline Cruise
Departing from Navy Pier, the Chicago: Lake Michigan Skyline Cruise provides a 30-45 minute journey showcasing the city’s iconic skyline and landmarks.
Priced at $37.57 per person, this cruise offers stunning panoramic views for photography enthusiasts. Passengers can witness key sites like the Willis Tower, Field Museum, and 360 Chicago while enjoying pre-recorded commentary in English or Spanish.
The cruise experience is further enhanced by the fast entry with a skip-the-line ticket. With an overall rating of 4.6/5 based on 701 reviews, this cruise is a popular choice among travelers, many of whom return for repeat experiences.
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Chicago City Tour With Architecture River Cruise Option
Offering a comprehensive exploration of Chicago, the Chicago City Tour with Architecture River Cruise Option provides visitors with an immersive experience showcasing the city’s iconic landmarks and architectural masterpieces.
With an exceptional 5-star rating and 95% traveler recommendation, this tour combines a guided bus tour and an optional river cruise, allowing guests to explore the city’s history and marvel at its stunning skyscrapers.
Highlights include panoramic views of Lake Michigan, photo stops at renowned landmarks, and an in-depth look at the architectural significance of the Chicago River.
Tailored for small groups, this tour offers a personalized and efficient experience, with complimentary hotel pickup and a flexible cancellation policy.
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Chicago: 1.5-Hour Lake and River Architecture Cruise
Immersing visitors in Chicago’s architectural marvels, the 1.5-Hour Lake and River Architecture Cruise takes passengers on a captivating journey through the city’s iconic waterways.
Priced from £35.32 per person, this 90-minute tour showcases the city’s historic and modern buildings along the Chicago River and Lake Michigan.
Led by expert local guides, the cruise highlights key landmarks like Marina City, Merchandise Mart, and Willis Tower.
Passengers can choose between outdoor deck or indoor climate-controlled seating and enjoy a full-service cash bar.
With an overall rating of 4.7/5 from 1,624 reviews, this tour offers an informative and memorable experience for those seeking to explore Chicago’s renowned architecture.
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Chicago Urban Adventure River and Lake Cruise
The Chicago Urban Adventure River and Lake Cruise provides visitors a captivating 90-minute journey through the city’s renowned waterways.
With a 95% recommendation rate and an impressive 4.5/5 overall rating, this tour offers an engaging exploration of Chicago’s skyline and architecture.
Guests can expect knowledgeable and entertaining guides, stunning views, especially at sunset and nighttime, and informative commentary on the city’s history.
However, some common complaints include long wait times before boarding and limited seating while waiting.
Nonetheless, this cruise is suitable for all age groups and provides excellent photo opportunities from the water.
Discounted parking is available, and the tour is easily accessible via public transportation.
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Chicago: 1.5-Hour Scenic Sunset Lake Cruise
Departing from the Chicago River at Michigan Avenue, the Chicago: 1.5-Hour Scenic Sunset Lake Cruise provides visitors a captivating journey through the city’s renowned waterways.
Priced from $45 per person, this 1.5-hour cruise offers stunning views of the Chicago skyline during sunset, as well as a passage through the Chicago Locks to reach the tranquil waters of Lake Michigan.
With a live tour guide, a full-service cash bar, and options for outdoor or climate-controlled seating, the cruise delivers an enjoyable experience.
Rated 4.6/5 based on over 600 reviews, the tour is praised for its professional crew, great views, and overall atmosphere.
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Best of Chicago Small-Group Tour With Skydeck and River Cruise
This small-group tour offers visitors a comprehensive exploration of Chicago’s iconic landmarks and breathtaking architecture.
With a maximum of 6-7 travelers, the tour provides a personalized experience, including hotel pickup, air-conditioned transportation, and all admission fees.
Highlights include ascending the Willis Tower’s Skydeck, marveling at the Cloud Gate sculpture, and embarking on a 1 hour 15 minute architectural river cruise.
The knowledgeable guide shares insightful commentary, and the flexible itinerary allows for visits to Buckingham Fountain and Adler Planetarium.
While some guests have expressed concerns about pickup logistics and value, the tour’s overall positive reviews suggest it’s an ideal option for first-time Chicago visitors seeking a well-planned introduction to the city’s top attractions.
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Chicago River: 1.5-Hour Guided Architecture Cruise
Visitors can experience a comprehensive tour of all three branches of the Chicago River on the Chicago River: 1.5-Hour Guided Architecture Cruise. Priced from $44 per person, this guided tour provides insights into Chicago’s iconic architecture from expert guides.
Passengers can choose between open-air decks or climate-controlled seating as they pass by landmarks like Marina City, Willis Tower, and Aqua at Lakeshore East. With a full-service cash bar and restroom access, the tour offers a comfortable experience.
Highly rated for knowledgeable guides, transportation, and value, the cruise receives 4.8/5 based on over 5,800 reviews.
Pets, weapons, and alcohol aren’t permitted, and all bags are subject to search for safety.
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Lake Michigan and Chicago River Architecture Cruise by Speedboat
The Lake Michigan and Chicago River Architecture Cruise by Speedboat offers a thrilling and informative tour of Chicago’s renowned waterways.
Lasting 75 minutes, the tour begins with an architectural cruise on the Chicago River, showcasing iconic landmarks like the Willis Tower and Tribune Tower.
Passengers then embark on a high-speed adventure along the shoreline of Lake Michigan, taking in stunning views of the city’s skyline, including Grant Park, the Museum Campus, and Buckingham Fountain.
With unobstructed vistas and knowledgeable tour guides, this cruise provides a unique perspective on Chicago’s rich architectural history and modern engineering feats.
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Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour
For an unforgettable perspective on Chicago’s renowned architecture and skyline, the Tall Ship Windy offers a captivating sailing tour.
This 148-foot traditional schooner takes passengers on a 75-minute cruise, with a live guide providing insightful narration in English. Guests can choose between an architecture and history-focused sail or a sunset sail, both offering breathtaking views of the city’s iconic skyscrapers.
Priced from €47.34 per person, the tour provides flexible booking and free cancellation up to 24 hours in advance.
While the experience has received mixed reviews, many praise the transportation and value for money.
Visitors should note the tour isn’t suitable for wheelchair users and smoking is prohibited.
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Chicago Educational Tour and Sail Aboard a Tall Ship
Chicago’s iconic skyline takes on a new perspective aboard the 148-foot Tall Ship Windy, where passengers embark on an educational tour and sailing adventure.
The 11 AM departure offers a family-friendly experience, with crew engaging travelers in activities like raising sails. Informative talks by the crew provide insights into the city’s architecture and Lake Michigan.
Travelers enjoy scenic views, a relaxing atmosphere, and the opportunity to help with sailing. With a 4.5-rating from 85 reviews, this tour is a must-do for visitors seeking an engaging and memorable way to explore Chicago from the water.
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Chicago: 90-Minute River and Lakefront Cruise at Night
Departing from the Chicago Riverwalk, this 90-minute cruise offers a unique perspective of the city’s iconic skyline and waterways.
Priced at $44 per person, the tour provides an evening tour of both the Chicago River and Lake Michigan, allowing visitors to admire the architectural wonders and twinkling lights of the city’s landmarks.
With a rating of 4.8 based on over 5,800 reviews, this cruise is a popular choice for those seeking a relaxing and visually stunning experience.
The cruise’s duration of 90 minutes ensures ample time to soak in the sights and appreciate Chicago’s stunning urban landscape from the water.
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Lake Michigan Skyline Cruise in Chicago
The Lake Michigan Skyline Cruise offers a 30-minute journey along the iconic waterfront, providing passengers with a unique vantage point to admire Chicago’s architectural marvels.
The pre-recorded commentary highlights the city’s landmarks, including the Willis Tower, John Hancock Center, and Aon Center. Guests can also spot the Gold Coast neighborhood and popular attractions like Navy Pier, Grant Park, and Buckingham Fountain.
While not wheelchair accessible, the cruise features a restroom and allows pets. Priced from $32.50 per person, the tour receives overwhelmingly positive reviews, with passengers praising the relaxing atmosphere and informative commentary.
Sunset cruises and special occasion celebrations are particularly recommended.
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Chicago: Family Fun Urban Adventure River and Lake Cruise
Exploring Chicago’s waterways offers families a captivating urban adventure on the Family Fun Urban Adventure River and Lake Cruise.
This 45-minute cruise showcases the city’s renowned architecture, providing a unique perspective from the water. With a 4.7-star rating from over 1,500 reviews, the cruise is a popular choice for families, delivering an entertaining and educational experience.
Priced at €26.52 per person, the cruise is an affordable way to discover the architectural wonders of Chicago.
Whether admiring the towering skyscrapers or learning about the city’s rich history, this family-friendly tour promises an engaging and memorable journey along the Chicago River and Lake Michigan.
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Chicago Skyline Tall Ship Sightseeing Cruise
Aboard the 148-foot schooner Windy, passengers embark on the Chicago Skyline Tall Ship Sightseeing Cruise, a captivating 75-minute journey that offers unparalleled views of Lake Michigan and the city’s iconic skyline.
Themed tours, including pirate and maritime stories as well as architectural-themed and sunset cruises, provide unique experiences. With a maximum capacity of 140 travelers, the cruise features live narration from expert guides and includes access to a restroom and the option to purchase alcoholic and non-alcoholic drinks and snacks.
While the cruise isn’t wheelchair accessible, guests must navigate a 6-step boarding ladder, making it suitable for those with a moderate level of physical fitness.
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Chicago: 75-Minute Architecture Cruise by Speedboat
For those seeking a faster-paced and up-close experience of Chicago’s renowned architecture, the 75-Minute Architecture Cruise by Speedboat offers an exhilarating alternative to the traditional sightseeing cruises.
This high-speed boat tour allows guests to zip along the Chicago River, offering unobstructed views of the city’s iconic skyscrapers and architectural gems.
With a duration of 75 minutes, the cruise is perfect for those with limited time or seeking an adrenaline-fueled experience.
Priced at $53.00 per person, the Architecture Cruise by Speedboat has earned a stellar 4.8 rating from over 4,000 customers, making it a popular choice among architecture enthusiasts and thrill-seekers alike.
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Chicago Shoreline Adventure Boat Tour
The Chicago Shoreline Adventure Boat Tour offers a thrilling high-speed sightseeing experience of the city’s iconic skyline.
With a maximum of 6 travelers, this small-group tour provides a personal and immersive way to explore Chicago’s waterfront. Highlights include the Museum Campus, Navy Pier, and Millennium Park.
The tour is suitable for adrenaline lovers and outdoor enthusiasts, with convenient departure times and a price starting from $90.00 per person. Guests will meet at the designated meeting point and walk to Dock J in Burnham Harbor to board the boat.
The tour isn’t recommended for those with certain medical conditions, but most travelers can participate. It’s no surprise the tour has earned a 100% recommendation from previous travelers.
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Chicago: Fireworks Cruise With Lake or River Viewing Options
Offering unbeatable views of the iconic Navy Pier fireworks, the Chicago Fireworks Cruise provides visitors with a unique vantage point to enjoy the dazzling display.
Cruising along Lake Michigan or the Chicago River, guests can choose between a 45-minute river tour or a 2-hour lake excursion.
Both options offer a full-service cash bar with locally sourced food and drinks. Passengers can also enjoy a brief architecture tour with light narration.
With an overall rating of 4.3 out of 5 based on 346 reviews, the Chicago Fireworks Cruise is a must-do summer activity in the city.
Prices start at $32 per person, and cruises run every Wednesday and Saturday during the summer.
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Chicago Skyline Sunset Sail Aboard a Tall Ship
Aboard the iconic tall ship Windy, guests can embark on a captivating Chicago Skyline Sunset Sail along the shores of Lake Michigan.
Launching from Navy Pier, this 148-passenger cruise offers breathtaking views of the city’s skyline as the sun dips below the horizon.
Guests can relax on board while enjoying included snacks, alcoholic beverages, and WiFi.
The crew’s professionalism and the relaxing atmosphere consistently earn high praise from reviewers.
While some note minor issues with seating comfort and timing, the majority of guests describe the experience as a must-do activity, praising the stunning scenery and the enjoyable overall experience.
Parking and arrival time are important considerations, as no refunds are provided for late arrivals.
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Chicago: Architecture Center Cruise on Chicagos First Lady
Operated by the Chicago Architecture Center, the Architecture Center Cruise aboard the Chicago’s First Lady river cruiser offers an immersive exploration of the city’s renowned architectural landmarks.
The 75-minute cruise showcases iconic buildings along the Chicago River, with expert commentary from trained docents. Priced at €50.19 per person, the tour is a popular skip-the-ticket-line option that allows visitors to admire the city’s stunning skyline and learn about its architectural history.
With a rating of 4.8 out of 5 from over 4,000 reviews, the Architecture Center Cruise is a must-do experience for anyone seeking to deepen their appreciation of Chicago’s architectural heritage.
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Chicago Private Sunset Sail on Lake Michigan
A private sunset sail on Lake Michigan in Chicago provides a unique opportunity to witness the city’s stunning skyline from a different perspective.
With 24 reviews and a 100% recommendation rate, this experience has earned a Badge of Excellence.
At $483.96 per group (up to 6 people), the 2-hour tour offers flexibility in booking and free cancellation up to 24 hours before.
Guests can enjoy beautiful views and pleasant conversation with the friendly Captain Mike.
However, the tour isn’t wheelchair accessible, and late arrivals may result in a shortened charter without refund.
COVID-19 guidelines include optional face masks and self-diagnosis before boarding.
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Recap
Chicago offers a variety of cruises and boat tours showcasing its stunning architecture and skyline. From family-friendly river cruises to sunset sails on Lake Michigan, there’s something for every interest and budget. Whether you’re looking to admire the city’s skyscrapers or enjoy a romantic evening on the water, these tours provide an unforgettable way to experience the beauty of Chicago from a unique perspective.