The 14 Best Cruises And Boat Tours in Chicago
Chicago’s skyline, sitting majestically beside Lake Michigan, is one of the most iconic cityscapes in the world. Its architecture is a showstopper, and seeing it from the water offers a whole new perspective. Whether you’re after a quick glimpse, a leisurely sunset cruise, or an in-depth exploration of the city’s architectural marvels, Chicago has a boat tour to match. From speedy speedboats zipping past skyscrapers to peaceful lake cruises at twilight, the options are plentiful.
In this guide, we’ll walk you through the best boat tours and cruises in Chicago, highlighting what makes each one special. We’ll cover everything from family-friendly adventures to small-group architectural explorations, helping you decide which fits your schedule, budget, and interests. Expect detailed insights on each tour’s itinerary, costs, and unique features — so you can book with confidence and make the most of your time on the water.
Quick Overview
This list features 14 top Chicago boat tours. You’ll find guided architecture cruises covering all three branches of the Chicago River, including skip-the-line options and small-group experiences. For lake lovers, there are scenic cruises on Lake Michigan, sunset rides, and even high-speed speedboat tours for thrill-seekers. There are family-friendly options with fun commentary, narrated daytime adventures, and night cruises showcasing the city’s glittering skyline.
Whether you want a relaxed sightseeing cruise, an adventure on a speedboat, or an educational exploration of Chicago’s architectural history, this guide has a lot to offer. Each tour offers a different flavor, so read on to find your perfect water-bound experience.
1. Chicago River: 1.5-Hour Guided Architecture Cruise
Starting with perhaps Chicago’s most renowned experience, this guided architecture cruise on the Chicago River is a classic. The $45 per person tour lasts 1.5 hours and features a live guide explaining the city’s architectural evolution. You’ll pass all three branches of the river, with options for outdoor or climate-controlled seating, making it comfortable year-round.
This tour is great for history buffs and architecture geeks alike. The expert guides share stories about legendary buildings like the Wrigley Building and the John Hancock Center, making it both educational and entertaining. Locally sourced food and drinks at a full-service bar add a convivial touch. Reviewers praise the guide’s enthusiasm and knowledge, with many noting it’s an experience that “started it all” in 1935.
Bottom Line: A well-rounded, engaging tour offering a deep dive into Chicago’s architectural legacy, ideal for first-timers or those wanting a comprehensive introduction.
2. Chicago: Architecture River Cruise Skip-the-Ticket Line
This popular skip-the-line cruise costs $49 per person and lasts 75 minutes. It’s perfect if you want to avoid long waits and get right on the water. The tour covers all three river branches, with a live docent pointing out 40 landmark buildings and explaining the nuances of Chicago’s architectural styles.
The expert narration and relaxed onboard atmosphere make it ideal for casual sightseeing. A cash bar provides drinks for those looking to toast the city’s impressive skyline. Reviewers consistently praise the guide’s knowledge, calling it “very interesting” and “highly recommendable.”
Bottom Line: Great for travelers who want a quick, efficient overview with expert commentary, especially if you’re on a tight schedule or want to skip the lines.
3. Chicago River Architecture Tour with Small Boat Upgrade Option
At $49, this 1.5-hour tour stands out for its in-depth approach and the option to upgrade to a small boat or a land-and-sea combo. The main focus is Chicago’s diverse architecture, from historic Art Deco buildings to soaring modern skyscrapers. The small boat upgrade allows for a more intimate experience, ideal for those who want a closer look and more personalized commentary.
This tour departs from Lake Shore Drive, giving great views of the city’s skyline. The guides are highly knowledgeable, offering insights into Chicago’s architectural movements and history. The small group size—capped at eight—means you’ll get plenty of attention and a less crowded experience.
Review quote: “The crew was very accommodating, and the tour was interesting and informative.”
Bottom Line: Perfect for architecture enthusiasts craving a more personal, detailed exploration of Chicago’s landmarks.
4. Chicago: 45-Minute Family-Friendly Architecture River Cruise
For families or those wanting a shorter, lively overview, this $28 tour lasts 45 minutes and features kid-friendly commentary. It’s designed to keep children engaged while still showcasing the city’s most spectacular buildings.
The tour is led by expert guides who make learning about Chicago’s architecture fun. It includes a full-service bar, and pre-purchased tickets help you skip long lines. Many reviews highlight the “amazing” guide and perfect length for younger audiences, with kids ranking it among their top Chicago experiences.
Bottom Line: A compact, engaging introduction for families wanting a quick yet informative water tour that keeps kids entertained.
5. Chicago: 1.5-Hour Lake and River Architecture Cruise
This $45 tour offers a 1.5-hour journey through both Lake Michigan and the Chicago River, combining city views with lakeside scenery. The tour begins at the Brainlab Training Center and takes you through the Chicago Lock, connecting the lake with the river.
The expert guides provide detailed commentary on Chicago’s iconic architecture, from historic towers to modern glass giants. The full bar with local beers and Garrett’s Popcorn makes it a true Chicago experience. Many reviewers say it’s “fun and informative,” especially appreciating the mix of water and skyline views.
Bottom Line: Best suited for those wanting a comprehensive experience, combining city architecture with lakeside vistas in one trip.
6. Chicago City Tour with Architecture River Cruise Option
For those who want a broad view of Chicago’s highlights, this $48.95 city tour lasts between 2 to 4 hours with an optional river cruise added. The tour uses a large-window minibus to explore downtown and North Side neighborhoods, with hotel pickup included.
Upgrade to include the river cruise and get a detailed look at Chicago’s architecture from the water. The small-group setting ensures a personalized experience. Past guests report the guide is “very knowledgeable and friendly,” and the tour is “very interesting,” making it ideal for first visits.
Bottom Line: A flexible option for those who want a mix of land and water sightseeing, with the convenience of hotel pickup.
7. Chicago: 1.5-Hour Scenic Sunset Lake Cruise
This $45 per person cruise captures Chicago’s magic at sunset. It lasts 1.5 hours, floating on Lake Michigan as the skyline turns golden. You can enjoy a glass of wine or craft cocktail as you soak in the view.
The cruise also passes through the Chicago Lock, linking the lake to the river. Reviewers call it “spectacular” and “romantic,” especially with the sunset backdrop. It’s a peaceful way to end a day in Chicago with the city’s lights gradually coming on.
Bottom Line: Ideal for a romantic outing or a relaxing evening, with a focus on scenic beauty and sunset views.
8. Chicago: Lake Michigan Skyline Cruise
For a quick but scenic look at Chicago from the water, this 45-minute cruise at $33 offers panoramic views of the skyline from Lake Michigan. Departing from Navy Pier, it’s perfect if you’re short on time but want a taste of lakeside beauty.
Audio commentary highlights major landmarks like Navy Pier and the Willis Tower. The relaxed pace makes it easy to take photos and enjoy the scenery. Many reviews praise its “enjoyable and informative” nature.
Bottom Line: A good choice for a brief lakeside experience, especially if combined with other city activities.
9. Lake Michigan Skyline Cruise in Chicago
This $32.50 45-minute cruise on Lake Michigan focuses on the skyline, offering fantastic views of Chicago’s high-rises. Passengers enjoy narrated sights of the city’s major buildings and famous landmarks like the Willis Tower.
Guests can bring lunch or drinks onboard, making it flexible for a midday break. Many reviewers describe it as “great views” with “wonderful staff.” It’s especially suitable for those wanting a laid-back cruise with good photo opportunities.
Bottom Line: Perfect for a quick, scenic lake outing with commentary and relaxed pacing.
10. Chicago: Narrated River and Lake Cruise by Night
For a magical view of Chicago’s glow, this $45 night cruise lasts 1.5 hours. You’ll glide along the Chicago River and Lake Michigan, witnessing the shimmering skyline and Buckingham Fountain’s lights.
The lively commentary shares stories behind the city’s landmarks, making it engaging and lively. Many reviewers call it “the highlight of our trip” and praise the “knowledgeable and funny” guide. It’s a memorable way to experience Chicago after sunset.
Bottom Line: Best for those wanting an evening escape with dazzling city views and storytelling.
11. Chicago: Architecture Boat Tour with Drinks
This $42 1.5-hour cruise offers a relaxed exploration of Chicago’s architecture with onboard drinks. You’ll pass by major sights like the Willis Tower, Wrigley Building, and Tribune Tower, enjoying commentary from guides.
Guests value the soothing atmosphere and the chance to sip a drink while learning about the buildings’ stories. Many reviewers say, “Incredibly knowledgeable guides and beautiful views.” It’s a top pick for anyone wanting a leisurely, informative experience with a drink in hand.
Bottom Line: Suited for those who want a laid-back sightseeing experience with the added comfort of drinks and commentary.
12. Chicago: Narrated Sightseeing River and Lake Cruise
This $45 1.5-hour cruise is perfect for families. It combines daytime river and lake views with lively narration about Chicago’s architecture and history. Kids and adults alike enjoy seeing Navy Pier, the Chicago Harbor Lighthouse, and the Museum Campus from the water.
Guests note the “very good” commentary and fun atmosphere. It’s a great way to introduce kids to Chicago’s skyline while enjoying a relaxed cruise.
Bottom Line: Ideal for families seeking a fun, engaging, and educational water tour.
13. City Cruises Chicago: 75-min Speedboat Architecture Cruise
For thrill-seekers, this $44 speedboat tour from Navy Pier offers an exhilarating ride. It combines the thrill of a speedboat with a comprehensive architecture tour on the Chicago River.
The live narration highlights key landmarks as you zip past skyscrapers. Many reviewers laud the guide’s humor and knowledge, calling it “stunning” even when cloudy. It’s a high-energy option for those who want an adrenaline rush with their architecture fix.
Bottom Line: Perfect for adventure lovers who want a fast-paced, energetic tour with memorable views.
14. Small-Group Sightseeing Boat Tour in Chicago
Finally, this $85 small-group tour is a 1 hour 30-minute exclusive experience aboard a US Navy-built RIB. Limited to 6 travelers, it offers a very intimate view of Chicago’s waterfront sights, including Navy Pier, Soldier Field, and the Shedd Aquarium.
Guests appreciate the personalized approach and safety, with life jackets provided. Many call it “a unique experience,” praising the ability to take photos and enjoy a relaxed atmosphere away from crowds.
Bottom Line: Best suited for those wanting a private, up-close perspective on Chicago’s landmarks with a maximum of six travelers.
How to Choose the Right Boat Tour in Chicago
When selecting a boat tour, consider your budget, interests, available time, and group size. If architecture is your main focus, the guided river cruises offer detailed insights, especially the small boat options for a more personal experience. For a family outing, look at shorter cruises like the 45-minute family-friendly tour, or the daytime river-lake combo for a broader perspective.
For romantic evenings, the sunset lakeside cruise or the nighttime skyline tour provides stunning views. If adrenaline is your thing, the speedboat architecture tour delivers excitement alongside great architecture commentary. Remember to book early during peak season, especially for popular tours like the Chicago River or Lake Michigan cruises.
Final Thoughts
Chicago’s boat tours offer a wide range of ways to see the city from the water, whether you’re after a relaxing sightseeing cruise, an educational architecture tour, or an adrenaline-pumping speedboat ride. For most travelers, the 1.5-hour guided architecture cruise provides a solid, informative experience, while the sunset lake cruise offers a romantic escape. Families and small groups might prefer the family-friendly or small-group options for a more tailored adventure.
If you want to see the city’s architectural marvels and enjoy the lakeside scenery, booking early and choosing a tour that matches your pace and interests can make all the difference. Now, grab your camera and get ready to see Chicago in a whole new light—on the water.