Chicago is a city best seen from the water. Its impressive skyline, historic buildings, and interesting bridges come alive when viewed from a boat. Whether you’re after a quick overview or a leisurely cruise, Chicago’s waterways offer a unique perspective that blends architecture, history, and fun. We’re particularly fond of the Chicago River: 1.5-Hour Guided Architecture Cruise for its comprehensive coverage and lively guides, or the Chicago: Shoreline Lake Michigan Skyline Cruise for a relaxed lakeside experience. The city’s diverse cruise options mean there’s something for all—from families to architecture buffs to romantic couples.
If you’re wondering which cruise to choose, this guide covers 16 of the best boat tours in Chicago, including architecture-focused cruises, scenic lake rides, speedboat adventures, and evening cruises. Each offers a different way to experience Chicago from the water, so read on for the full rundown.
1. Chicago River: 1.5-Hour Guided Architecture Cruise
This popular architecture cruise is a classic for a reason. For about $45 per person, you get a 1.5-hour journey through all three branches of the Chicago River, with live commentary from a fun, local guide. This tour started the city’s river cruise craze back in 1935, and it still sets the bar for exploring Chicago’s iconic skyline from the water. You can choose between outside deck-top or indoor climate-controlled seating, making it comfortable year-round.
What makes this cruise stand out is the combination of history, humor, and insight. The guide will explain how Chicago’s architecture evolved, highlighting structural milestones like the Willis Tower and historic bridges. The full-service cash bar offers locally sourced food and drinks, adding a relaxed, social vibe. Reviewers love the “skips the line” ticket option for ease and the lively guides who make the stories come alive. Bottom line: a well-rounded introduction to Chicago’s architectural marvels.
2. Chicago: Architecture River Cruise Skip-the-Ticket Line
This 75-minute tour offers a speedier, no-waiting experience at just $48 per person. It covers all three branches of the Chicago River, with a live docent explaining about approximately 40 landmark buildings. It’s ideal if you want a deeper dive into Chicago’s skyline without the longer time commitment.
What makes this tour unique is its focus on in-depth narration and the opportunity to relax with a drink from the cash bar. The boat’s proximity to key sights allows for great photos, and the guide’s insights make it a hit with those who love architecture details. The skip-the-line feature is practical, especially during busy seasons. Perfect for travelers who want a shorter but rich experience of Chicago’s architecture.
3. Chicago: 45-Minute Family-Friendly Architecture River Cruise
For families looking for a shorter, engaging outing, this 45-minute cruise costs $28 per person. It provides a lively, family-friendly commentary on Chicago’s landmarks, making the city’s architecture accessible to kids and adults alike. The full-service cash bar remains available for parents wanting a drink while the kids enjoy the ride.
This tour is ideal if you’re tight on time but still want to experience Chicago from the river. With a focus on fun stories and quick highlights, it appeals to those traveling with children or anyone new to the city’s architecture. Reviewers appreciate the pre-purchased tickets to skip lines and the friendly guides who keep things lively. Bottom line: a quick, family-friendly way to see Chicago’s iconic buildings.
4. Chicago: 1.5-Hour Lake and River Architecture Cruise
This dual-water cruise combines the best of both worlds—Lake Michigan and the Chicago River. For $45, you’ll learn about Chicago’s architecture from expert guides while cruising through the legendary Chicago Lock, connecting the lake to the river. The boat offers both outside deck seating and climate-controlled interiors, depending on weather.
What sets this tour apart is the chance to see Chicago’s skyline from the shoreline and the riverfront in one trip. The inclusion of Garrett’s Popcorn and locally sourced drinks makes the experience special. Reviews rave about the knowledgeable guides and the scenic views. It’s ideal for those wanting an in-depth, panoramic view of the city’s architecture from multiple perspectives.
5. Chicago City Tour with Architecture River Cruise Option
This combined city bus and optional boat tour provides a comprehensive Chicago experience. For about $49, you get a 2-4 hour mini-bus tour with hotel pick-up, visiting landmarks like Millennium Park, The Bean, and Buckingham Fountain. You can upgrade to include a specialized architecture boat cruise on the river.
What makes this a top choice is its flexibility; you see the city from land and water in one package. The small-group setting ensures a tailored experience, praised for its knowledgeable guides. It’s perfect if you want a broad overview with the option to focus on architecture. The tour is especially suited for first-time visitors wanting a detailed, personalized introduction.
6. Chicago by Night River and Lake Cruise
This evening cruise transforms Chicago’s skyline into a glittering spectacle. Costing $45, it lasts 1.5 hours and offers panoramic views of the city lit up at night, including the Buckingham Fountain’s light display. As you glide along the river and Lake Michigan, the lively commentary brings the city’s history to life.
This cruise is perfect for couples or anyone looking to see Chicago’s skyline in a different light. The night views are spectacular, and the atmosphere is relaxed and romantic. It’s a great way to end a day in Chicago, especially if you enjoy city lights and a bit of storytelling.
7. Chicago: Shoreline Lake Michigan Skyline Cruise
This 45-minute lakeside cruise offers a straightforward way to see Chicago’s lakeshore and skyline from Lake Michigan for just $38. The pre-recorded commentary provides insights into Chicago’s major landmarks like Navy Pier, the John Hancock Center, and the Willis Tower.
Ideal for a quick sightseeing stop or a relaxing afternoon, it’s a no-fuss option with fast entry to avoid lines. Photographers will appreciate the panoramic views, making it perfect for capturing Chicago’s iconic buildings from a water-level perspective.
8. Chicago: 1.5-Hour Scenic Sunset Lake Cruise
Watch the sun set over Lake Michigan on this romantic 1.5-hour cruise priced at $45. It’s a tranquil way to end the day, with the city skyline glowing in the background. The cruise includes a full-service cash bar featuring local beer, spirits, and Garrett’s Popcorn.
This experience appeals to couples or those seeking a peaceful, scenic adventure. The sunset views over Chicago’s skyline are particularly stunning, especially during spring and summer. Reviewers love the relaxing atmosphere and the chance to toast the evening with a drink.
9. Chicago Architectural River Cruise
This 1 hour 30-minute tour focuses solely on Chicago’s architecture, highlighting over 50 skyscrapers, bridges, and historic sites. It’s a laid-back cruise with complimentary refreshments and fascinating stories about Chicago’s development. The tour is wheelchair accessible, making it inclusive.
What sets this apart is its deep dive into Chicago’s architectural evolution, from the Great Chicago Fire’s aftermath to modern designs like Aqua by Jeanne Gang. Reviewers praise the knowledgeable guides and the engaging storytelling. It’s perfect for architecture enthusiasts wanting a detailed, relaxed experience.
10. Chicago: Architecture Boat Tour with Drinks
This 1.5-hour guided boat cruise offers a relaxing way to see the city’s skyline, with a full-service cash bar serving drinks from local breweries and spirits. Passing by Willis Tower, Wrigley Building, and Tribune Tower, it combines scenic views with informative commentary.
Ideal for those who like to sip while sightseeing, this tour earns praise for its comfort and relaxed vibe. It’s a good mid-range option for a casual, informative cruise with a socially convivial atmosphere.
11. Lake Michigan Skyline Cruise in Chicago
This 45-minute lakeside cruise costs just $32.50 and is perfect for a quick, scenic water ride. It offers panoramic views of Chicago’s skyline and major landmarks like Navy Pier and the Willis Tower, with pre-recorded commentary.
A great pick for budget-conscious travelers or those short on time, it’s straightforward but provides a solid water-level perspective of Chicago’s architecture. It’s especially recommended in good weather for the best views.
12. Chicago: Architecture Center Cruise on Chicago’s First Lady
This 1.5-hour cruise pairs with the Chicago Architecture Center and features live narration by certified docents. You’ll view over 50 buildings and 13 bascule bridges, gaining a detailed understanding of the city’s architectural story.
This tour is ideal for those wanting an educational experience with unobstructed 360-degree views from open decks. The option to add entrance to the Architecture Center makes it a deep dive into Chicago’s design history. Highly recommended for architecture buffs.
13. Chicago Sightseeing River and Lake Cruise
This 1 hour 30-minute cruise combines river and lake exploration for $45. It offers stories about Chicago’s landmarks like Navy Pier, Wrigley Building, and Soldier Field, along with impressive skyline views from Lake Michigan.
Perfect for those who want a mix of river and lakeshore sights, with fun commentary and photo opportunities. It’s a versatile choice for families or anyone wanting a comprehensive water-based tour of Chicago.
14. Chicago: Narrated Sightseeing River and Lake Cruise
This 90-minute fully narrated tour is ideal for family groups. It covers Chicago’s skyline, historic buildings, and Lake Michigan scenery—complete with lively commentary that makes history accessible and engaging.
Reviewers appreciate the detailed narratives and the chance to see Navy Pier, Chicago Harbor Lighthouse, and Museum Campus. It’s a lively, educational cruise suited for all ages.
15. City Cruises Chicago: 75-min Speedboat Architecture Cruise
For an adrenaline rush, this speedboat tour departs from Navy Pier, combining speed, scenery, and architecture. It’s a 75-minute ride costing about $44, with a high-speed splash on Lake Michigan at the end.
It’s perfect for thrill-seekers who want a fast-paced, up-close view of Chicago’s iconic buildings like Tribune Tower and Merchandise Mart. Reviewers highlight the exhilarating ride and the panoramic water views—an adrenaline-packed way to see the city.
16. Chicago: City Minibus Tour with Optional Architecture Cruise
This flexible tour combines a land-based minibus tour of downtown and nearby neighborhoods with the option to add a 75-minute architecture cruise. For about $49, you get a 2-4 hour overview with photo stops at iconic spots like The Bean and Buckingham Fountain.
Ideal for those who want to see Chicago from both land and water, it offers a practical, customizable experience. The small-group format and expert guides make it especially appealing for first-time visitors or those wanting a well-rounded day.
How to Choose the Best Boat Tour in Chicago
When deciding which cruise suits your style, consider your budget, time, and interests. If architecture is your focus, the Chicago River: 1.5-Hour Guided Architecture Cruise or the Chicago: Architecture Center Cruise on Chicago’s First Lady provide deep dives. For a quick snapshot, the Lake Michigan Skyline Cruise or Shoreline Lake Michigan Skyline Cruise are perfect.
Families might prefer the 45-minute Family-Friendly Architecture River Cruise, while couples seeking romance may love the Sunset Lake Cruise or the By Night River and Lake Cruise. Adventure seekers should try the Speedboat Architecture Cruise, which combines scenery and thrills. Booking early is recommended during peak seasons, especially for popular tours like the Lake and River combination or the architecture-focused cruises.
In summary, Chicago offers a rich variety of boat tours tailored to different tastes—whether you’re after stunning skyline views, architectural insights, or lakeside relaxation. For a comprehensive experience, the Chicago River: 1.5-Hour Guided Architecture Cruise and the Chicago: Shoreline Lake Michigan Skyline Cruise stand out as top choices. Families and casual visitors will appreciate shorter, family-friendly options, while architecture enthusiasts can indulge in detailed guided tours.
No matter what you pick, booking ahead ensures a smooth trip—Chicago’s waterways are bustling, and these tours often sell out. Get ready to see the Windy City from a whole new angle—on deck, on the water, and with plenty of stories to tell.