The 16 Best Cruises And Boat Tours in Chicago
Chicago’s famous skyline isn’t just best viewed from land — it’s best seen from the water, especially when you’re floating past soaring skyscrapers, iconic landmarks, and shimmering waves on Lake Michigan. The city’s waterfront is a treasure trove for boat lovers, with options that range from short sightseeing trips to in-depth architectural explorations, and even romantic sunset cruises. Whether you want a family-friendly outing, a speedy speedboat adventure, or an insider’s look with a knowledgeable guide, Chicago’s water-based tours deliver a different perspective on the Windy City. Planning ahead helps, as many tours fill quickly, especially in peak seasons.
In this guide, we’ve listed the best cruises and boat tours in Chicago based on variety, reviews, and what makes each stand out. From historic architecture to stunning lake views, our list covers options for every interest and schedule. Dive into detailed descriptions to find the one that best matches your trip style.
1. Chicago River: 1.5-Hour Guided Architecture Cruise
At number 1, this classic architecture tour is the original Chicago river cruise, dating back to 1935. It’s a popular choice, rated 4.8/5 from over 6,400 reviews, and offers an immersive experience with a live, fun guide pointing out Chicago’s iconic architectural marvels. The 1.5-hour trip covers all three branches of the river, with options for outside deck seating or indoor climate-controlled comfort. The tour includes detailed commentary about Chicago’s skyline development, complemented by locally sourced food and drinks at a full-service cash bar.
Guests praise the engaging guides, especially noting how the architecture stories bring the buildings to life. The tour starts at the Brainlab Training Center and passes landmarks like Marina City, Willis Tower, and Tribune Tower. Visitors often comment on its value, given the skip-the-line ticket option and the rich knowledge shared. This tour suits those who love architecture, city history, and a lively, social atmosphere.
Bottom Line: An iconic, well-reviewed option perfect for architecture enthusiasts and first-time visitors who want to get a comprehensive look at Chicago’s skyline from the river.
2. Chicago: Architecture River Cruise Skip-the-Ticket Line
Also rated 4.8/5 with over 4,100 reviews, this skip-the-line architecture cruise offers a slightly shorter 75-minute experience that dives into Chicago’s most famous buildings. It features a live narration about 40 landmark structures and a cash bar to relax during the trip. This tour’s streamlined access means less waiting, making it easier to fit into a busy day.
Guests often comment on the diversity of architecture and the engaging guide, who makes the city’s landmarks come alive. The tour covers all three river branches, with highlights like the Merchandise Mart, Willis Tower, and NBC Tower. It’s particularly suited for travelers who value efficiency but still want a thorough story behind Chicago’s architectural feats.
Bottom Line: A well-rated, efficient choice for travelers eager to combine architecture insight with quick access to a popular tour.
3. Chicago River Architecture Tour with Small Boat Upgrade Option
Rated 5.0/5 from 818 reviews, this small boat tour is perfect for architecture lovers wanting a more intimate experience. Starting at Lake Shore Drive, the 1.5-hour tour explores highlights like the Chicago skyline, Navy Pier, and the famous “Bean.” The tour shares insights into the architectural movements that shaped the city, with an option to upgrade to a smaller vessel or land-sea combo for a broader exploration.
Guests rave about the personalized attention and the passionate guides who share personal stories. The tour is ideal for travelers who enjoy a relaxed, in-depth look at Chicago’s buildings and prefer a less crowded boat. The detailed narration and the chance to see the city from a new perspective makes this a standout choice.
Bottom Line: An excellent option for architecture fans who want a deeper, more personal experience with expert guides.
4. Chicago: 45-Minute Family-Friendly Architecture River Cruise
Rated 4.7/5 from over 1,700 reviews, this family-oriented cruise offers a shorter, 45-minute trip with lively, family-friendly commentary. It navigates the downtown riverfront, passing major landmarks like the Willis Tower and the Tribune Tower. The full-service cash bar allows parents to relax while kids stay engaged with fun facts about Chicago’s architecture.
Reviewers highlight how well the guide kept children entertained, with many citing it as a highlight of their trip. It’s perfect for families with young children or those with limited time but still wanting a taste of the city’s skyline. The shorter length makes it easier for kids to stay attentive, and the accessible boarding process simplifies logistics.
Bottom Line: A fun, quick introduction to Chicago’s architecture for families or travelers short on time.
5. Chicago: 1.5-Hour Lake and River Architecture Cruise
Rated 4.7/5 from 1,697 reviews, this cruise combines both Lake Michigan and Chicago River sights in one trip. It’s the only tour that links these two iconic waterways, offering a comprehensive view of Chicago’s skyline. The trip includes a skip-the-line ticket, expert guides, and a full-service cash bar featuring local products.
Highlights include passing through the Chicago Lock, with views of buildings like the Lake Point Tower, Tribune Tower, and Willis Tower. Guests love the insider stories and the way the tour bridges the city’s lakeside and downtown architecture. The 1.5-hour duration makes it manageable for most travelers seeking a thorough overview.
Bottom Line: A top choice for those wanting to see both lakefront and riverfront architecture in one trip.
6. Chicago City Tour with Architecture River Cruise Option
Rated 5.0/5 from 654 reviews, this combination city and river tour offers a land-and-water perspective with hotel pickup. You explore downtown and North Side neighborhoods on a minibus, with join-in or optional architecture cruise. The tour highlights popular sites like the Bean, Buckingham Fountain, and Museum Campus, with a short river cruise upgrade.
Guests appreciate the personalized experience of the small group and the flexibility to see Chicago’s landmark buildings from different angles. It’s suited for travelers who want a broad overview with the option to add a river cruise for architecture buffs.
Bottom Line: Ideal for those who want a flexible, comprehensive Chicago experience, combining land and water.
7. Chicago: 1.5-Hour Scenic Sunset Lake Cruise
Rated 4.7/5 from nearly 660 reviews, this sunset cruise is perfect for a romantic or peaceful end to the day. It offers stunning sunset views against the Chicago skyline, with a relaxed 1.5-hour ride on Lake Michigan. You can toast with a drink from the cash bar while watching the city’s lights come alive.
Guests mention how beautiful the sunset is over the city, creating memorable photographs. It’s best suited for travelers seeking a serene, picturesque experience rather than a detailed tour. The cruise also offers a skip-the-line option, so arriving early is still recommended.
Bottom Line: A tranquil, romantic trip ideal for sunset lovers and those wanting a quiet moment with city views.
8. Chicago: Lake Michigan Skyline Cruise
Rated 4.6/5 from over 700 reviews, this short sightseeing cruise along Lake Michigan focuses on panoramic views of the skyline. It’s a 45-minute trip with pre-recorded commentary about the city’s architecture and history. The cruise features stops at Navy Pier, the Willis Tower, and the Field Museum for ideal photo opportunities.
Guests find this a great value at just $33, especially for those with limited time or looking for a quick, scenic overview. The fast entry tickets make boarding smooth, and the views of the city from the water are memorable.
Bottom Line: Best for travelers seeking a quick, affordable lakefront view with good commentary.
9. Lake Michigan Skyline Cruise in Chicago
Rated 4.5/5 from 767 reviews, this laidback lake cruise offers 45 minutes of cityscape views with engaging audio narration. It’s a relaxed way to see major landmarks such as Navy Pier, the John Hancock Center, and Buckingham Fountain, with the option to bring your own lunch or buy drinks onboard.
Guests love the panoramic vistas and the flexibility to enjoy the scenery at their own pace. It’s perfect for families, couples, or solo travelers wanting a peaceful experience without too much walking or standing.
Bottom Line: An easygoing option for scenic lakefront sightseeing with the convenience of bringing your own food.
10. Chicago: Narrated River and Lake Cruise by Night
Rated 4.6/5 from 561 reviews, this evening cruise offers a dazzling view of Chicago’s nighttime skyline. It combines the river and lake routes in a 1.5-hour trip, with lively commentary about the city’s architectural highlights and amazing light displays like Buckingham Fountain.
Reviews mention how the night views make the city sparkle, and the guides keep the atmosphere lively and engaging. It’s perfect for a special night out or those who want to see the city’s lights reflected on the waters.
Bottom Line: A memorable, illuminated experience suited for romantic evenings or night photography.
11. Chicago: Architecture Boat Tour with Drinks
Rated 4.7/5 from 376 reviews, this architecture cruise includes a full bar onboard, perfect for relaxing while learning about Chicago’s iconic buildings. It’s a 1.5-hour trip passing by landmarks like the Wrigley Building and Tribune Tower with commentary explaining the architecture.
Guests say the guides’ stories make the buildings come alive, and the drinks add to the relaxed vibe. It’s a great pick for those who want a casual yet informative experience.
Bottom Line: An enjoyable, drink-inclusive cruise ideal for relaxed sightseeing.
12. Chicago: Narrated Sightseeing River and Lake Cruise
Rated 4.7/5 from 231 reviews, this 90-minute fully narrated tour covers both the river and lake, offering families a lively, informative experience. It offers views of Navy Pier, Museum Campus, and the Chicago Harbor Lighthouse, with stories about the city’s architecture and development.
Guests appreciate the engaging guides and the opportunity to see Chicago from both water routes. It’s suited for those who want a comprehensive, fun overview of the city’s highlights.
Bottom Line: A family-friendly, detailed tour providing a broad look at Chicago’s skyline and landmarks.
13. City Cruises Chicago: 75-min Speedboat Architecture Cruise
Rated 4.6/5 from 247 reviews, this speedboat adventure combines a fast-paced 75-minute cruise with Lake Michigan thrill rides. Boarding at Navy Pier, you’ll see city landmarks like the Tribune Tower, Wrigley Building, and Merchandise Mart, then zoom across Lake Michigan for a high-energy ride.
Guests love the exciting speedboat ride combined with informative narration about Chicago’s architecture. The adrenaline factor makes it ideal for travelers seeking a fun, active experience with a city tour twist.
Bottom Line: Perfect for thrill-seekers who want to combine sightseeing with a high-speed boat ride.
14. Small-Group Sightseeing Boat Tour in Chicago
Rated 5.0/5 from only 72 reviews, this exclusive small-group RIB boat tour offers a more personal experience. With just six travelers, you explore Navy Pier, Soldier Field, and the Chicago River, with commentary on local landmarks and architecture.
Reviews highlight how knowledgeable and personable the guide is, making this a perfect choice for travelers who want an intimate, tailored experience. Safety is prioritized with provided life jackets, and the small group size encourages questions and close-up views.
Bottom Line: An excellent pick for those wanting an exclusive, small-group boat experience with expert narration.
15. Chicago: City Minibus Tour with Optional Architecture Cruise
Rated 4.8/5 from 123 reviews, this combination minibus and boat tour lets you explore Chicago’s main sights on land, with the option to add a 75-minute architectural cruise. Highlights include Buckingham Fountain and views of the downtown skyline.
Guests appreciate the flexibility of the tour, and the hotel pickup makes logistics easier. It’s perfect for travelers who want a broad overview plus a water perspective without booking separate tours.
Bottom Line: Versatile and convenient, suited for those who want a comprehensive Chicago experience with optional water sightseeing.
16. Chicago Seadog River & Lake Architectural Tour
Rated 4.5/5 from 235 reviews, this dual experience combines a river cruise with a speedboat ride on Lake Michigan. It covers landmarks like Willis Tower on the river and offers a thrilling ride on the lake, with lively commentary throughout.
Reviewers mention how fun and exciting the speedboat segment is, with many noting the spectacular views and the engaging guide. It’s best for travelers seeking an active, high-energy way to see Chicago from the water.
Bottom Line: A dynamic tour for those who want a mix of sightseeing and adrenaline on Lake Michigan.
How to Choose the Best Boat Tour in Chicago
When selecting a cruise, consider your interests: architecture buffs may prefer the detailed architecture cruises, while families might go for the family-friendly river tour. Budget-conscious travelers can find excellent options at around $30-$45, like the Lake Michigan Skyline Cruise, whereas thrill-seekers should look at the high-energy speedboat tours.
Also, think about timing: a sunset cruise offers romantic views, and the night tour is perfect for evening sightseeing. Booking early during peak months is advisable, especially for popular skip-the-line options.
Wrapping Up
Chicago’s water tours cover a wide spectrum — from detailed architecture stories to lively speedboat rides and tranquil lake sunsets. For a comprehensive architectural overview, the Chicago River: 1.5-Hour Guided Architecture Cruise is a top choice, while families or those on a budget might prefer the family-friendly 45-minute cruise. For thrill-seekers, the speedboat architecture tour offers a fun, fast-paced experience.
No matter your preference, early booking helps ensure you get a spot on the tour that best fits your style. With so many options, your water adventure in Chicago promises to be memorable and full of stunning views.