View of the tourists on the Shoreline Sightseeing boat during one of the best Chicago River tours

10 Best Chicago River Tours in 2023 (By a Local)

As a Chicago local of over 5 years, I can’t recommend a Chicago River tour enough. Chicago has one of the world’s most iconic skylines, and it looks astounding from the water.

There are plenty of interesting attractions to see in Chicago. Booking a boat tour gives you a unique view of the city and is a great way to see the sights. From fancy dinner cruises with live entertainment to party boats with tiki bars and even kayaking, there’s a Chicago River boat tour that’s perfect for you.

I’ve compiled a list of Chicago boat tours, any of which could help make your visit unforgettable!

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Best Chicago River Tours

Chicago Line Cruises

A phenomenal way to learn about Chicago architecture while enjoying beautiful views of the landmarks.

View of the tourists and the guide o the boat with the Chicago skyscrapers in the background
Guided river tour through Downtown Chicago (photo: Tepikina Nastya / Shutterstock)
  • ⌚ Length: 1.5 Hours
  • 🌟 Guest Reviews: 4.5/5 Stars
  • 🗺️ Highlights: Historical lesson, Willis Tower, Trump Tower 
  • ✅ Includes: Tour guide, cookies, beverages (coffee/tea, and soft drinks)
  • 👉 Check prices & availability here

Chicago Line Cruises offers several fantastic river tour options for history buffs and music lovers. 

The Architectural Tour will take you down the Chicago River. As you’re sailing, your guide will tell you about the Great Chicago Fire that necessitated a reconstruction of much of the city.

On the Chicago Line Cruises Historical Tour, see exclusive photos from the archives of the Chicago History Museum. Learn the story of the city that lifted itself towards the sky with newer and taller buildings after the Great Chicago Fire.

And the Live Jazz Cruise allows you to enjoy Geordie Kelly and his band’s iconic Chicago jazz style while you sail down the river.

Shoreline Sightseeing

A fun way to learn about Chicago’s architecture is from the Chicago River or Lake Michigan.

View of the tourists on the Shoreline vessel passing under the bridge in Chicago River
A Shoreline vessel on the Chicago River (photo: big joe / Shutterstock)
  • ⌚ Length: 0.5 – 1.25 Hours
  • 🌟 Guest Reviews: 5/5 Stars
  • 🗺️ Highlights: Sailing, John Hancock Center, Chicago Architecture Center 
  • ✅ Includes: Live narration of architectural facts, tour
  • 👉 Check prices & availability here

Shoreline Sightseeing’s Architecture River Tour departs from either Navy Pier or Michigan Avenue. It will show you more than 40 of Chicago’s most famous buildings while cruising down the three branches of the river. See Tribune Tower, the John Hancock Center, and so much more!

The Skyline Lake Tour gives you a relaxing cruise on the waters of the lake. It gives you a bit more distance from the architecture than the river tour. You can take stunning panoramic photos of Chicago’s skyscrapers. 

Shoreline Sightseeing also offers fireworks tours during the summer when Navy Pier has a weekly sparkler show!

Safety measures are taken on these tours, with sanitization procedures in place for high-traffic areas.

Odyssey Dining Cruises

A dining cruise with a panoramic view of city architecture as a backdrop.

  • ⌚ Length: 2 – 3 Hours
  • 🌟 Guest Reviews: 4/5 Stars
  • 🗺️ Highlights: Dining, Chicago landmarks, Chicago River/Lake Michigan 
  • ✅ Includes: Lunch and narration about architecture OR dinner and DJ entertainment
  • 👉 Check prices & availability here

Odyssey Dining Cruises offer excellent Chicago lake and river boat tours for those who want a meal with their sightseeing.

The lunch cruise lasts for two hours and includes a three-course meal (salad, main course, and dessert) in a glass vessel with an incredible view. Take in the narration about surrounding Chicago landmarks. Among these are the Civic Opera House and Merchandise Mart.

The Chicago River dinner cruise takes you along the same route but with DJ entertainment. Enjoy a three-course meal with complimentary tea and coffee, or purchase a cocktail.

Alternatively, enjoy an evening cruise on the lake. Board the luxury yacht at Navy Pier, and dine with breathtaking views of the Chicago skyline. Odyssey also offers fireworks dinner cruises during the summer.

Free cancellation is possible up to 24 hours before most tours.

📚 Related Reading: Want to find a place to stay close to the lake and river cruises? Check out my guide on where to stay in Chicago!

Wendella Tours and Cruises

The quintessential Chicago boat tour, showing you the area from many angles.

View of the Wendella boat sailing along the Chicago river with the cityscape in the background
A Wendella boat sailing along the river (photo: rSnapshotPhotos / Shutterstock)
  • ⌚ Length: 0.75 – 1.5 Hours
  • 🌟 Guest Reviews: 4.5/5 Stars
  • 🗺️ Highlights: Sailing, Chicago River, Lake Michigan 
  • ✅ Includes: Tour guide, live commentary about architecture
  • 👉 Check prices & availability here

Wendella offers a variety of boat tours with options for every interest. 

The 45-minute Chicago River Architecture Tour starts at the Magnificent Mile. It takes you past several Chicago landmarks. These include the Michigan Avenue Bridge, the Chicago Riverwalk, and the twin “corn cobs” of Marina City in River North.

There’s also the 90-minute Chicago Lake and River Architecture Tour. It begins at the Michigan Avenue Dock and gives you views of iconic architecture on the river and lake. The Chicago Sunset Cruise allows you to see the sun set behind the skyline and the lights of nighttime Chicago.

Wendella also offers specialty cruises, featuring events like firework shows and wine tasting. Free cancellation is an option for up to 24 hours before most tours.

Chicago’s First Lady Cruises

The most comprehensive tour of the Chicago waters.

View of the cityscape and the Chicago's First Lady sailing under a bridge on Chicago River
Chicago’s First Lady on the historic Chicago River (photo: Itz Universal Fotos / Shutterstock)
  • ⌚ Length: 0.75 – 1.5 Hours
  • 🌟 Guest Reviews: 5/5 Stars
  • 🗺️ Highlights: Sailing, Chicago River, Chicago Riverwalk
  • ✅ Includes: Detailed narration about buildings, tour
  • 👉 Check prices & availability here

Chicago’s First Lady is in collaboration with the Chicago Architecture Center (CAC). It offers the most complete tour of Chicago’s skyline you can find, as docents must complete 100 hours of training.

The CAC River Cruise is the #1 rated boat tour in the Windy City. The expert guides tell compelling stories about the formation of Chicago. The memorable Evening River Cruise gives you the unique opportunity to view the city’s landmark buildings as the sun goes down.

All First Lady watercraft include climate-controlled interiors, full-service bars, and open-air top decks. These are great options for anyone who wants a private tour or a private yacht event. Chicago’s First Lady is affiliated with multiple caterers who can make your event memorable.

Island Party Boat

A beach party on a boat with great views.

A tiki-themed Island Party Boat sailing on the Chicago River
A tiki-themed Island Party Boat on the Chicago River (photo: Page Light Studios / Shutterstock)
  • ⌚ Length: 1.25 – 1.5 Hours
  • 🌟 Guest Reviews: 4/5 Stars
  • 🗺️ Highlights: Sailing, island-themed party, city buildings
  • ✅ Includes: Island tunes, narration about attractions, tiki bar
  • 👉 Check prices & availability here

You can board this boat at the Island Party Hut at the Chicago Riverwalk or at Monroe Harbor. This gives you the unique experience of a simultaneous tour and island party.

You can do the standard tiki bar river cruise, tiki bar fireworks cruise, or mimosa tiki bar cruise. Cocktails are available for purchase, and you can take in info about everything you’re seeing from the captain.

And perhaps the best part – if you’re traveling with your dog, you can bring them along!

SeaDog Cruises

A thrill ride with fun facts about Chicago thrown in!

A tour guide speaking in front of the tourists o the SeaDog boat with the Chicago Harbor Lighthouse view
Passengers on a SeaDog boat (photo: Rajesh Vijayakumar / Shutterstock)
  • ⌚ Length: 0.5 – 1 Hour
  • 🌟 Guest Reviews: 4.5/5 Stars
  • 🗺️ Highlights: Speedboat ride, Lake Michigan, city buildings
  • ✅ Includes: Thrill ride, narration about buildings
  • 👉 Check prices & availability here

SeaDog Cruises gives you the chance to speed across Lake Michigan. There are all sorts of fun twists and turns, splashes, and crazy speeds. They put a unique spin on the experience as you learn facts about landmarks from your tour guide.

This 30-minute thrill ride starts at Navy Pier and passes iconic attractions. These include Grant Park, the Museum Campus, and Buckingham Fountain. There is also a 60-minute fireworks cruise that allows you to observe the Pier’s sparkler show in all its splendor from the lake.

Chicago Fireboat Tours

A ride along the historic Chicago River in a historical retired fireboat.

A Chicago fireboat docked on Chicago River
A Chicago fireboat (photo: Andy Sutherland / Shutterstock)
  • ⌚ Length: 1.5 – 2 Hours
  • 🌟 Guest Reviews: 5/5 Stars
  • 🗺️ Highlights: Sailing, focus on fireboat, Chicago buildings
  • ✅ Includes: Chance to see museum inside watercraft, narration about buildings and the watercraft
  • 👉 Check prices & availability here

These boat tours are unique in that they involve contact with an actual piece of Chicago’s heritage. This is a retired fireboat, specifically the Fred A. Busse, Engine 41. It served the city between 1937 and 1981. There’s a small museum on the interior with photos of this boat while it was in service, in addition to all sorts of cool firefighting artifacts.

Chicago Fireboat Tours will take you along the river and lake. Here, you’ll learn cool facts about buildings in Chicago in addition to historical gems about the boat. There’s also the Sunset Brew Cruise on Thursdays between May and September at sunset. This adult-only cruise gives you the chance to enjoy local craft beers and great music while seeing the sights.

Urban Kayaks

A chance to paddle your way through the landmarks of Chicago.

Two people kayaking on Chicago River with the skyscrapers in the background
Kayakers on the Chicago River (photo: anderm / Shutterstock)
  • ⌚ Length: 1.5 – 2 Hours
  • 🌟 Guest Reviews: 5/5 Stars
  • 🗺️ Highlights: Kayaking, Chicago River/Lake Michigan, Chicago buildings
  • ✅ Includes: Kayaking lesson, option for a guided tour
  • 👉 Check prices & availability here

Urban Kayaks in River North allows you to explore Chicago’s waters and get some exercise at the same time! You actually get to go kayaking for this one. All experience levels are welcome, as you do get a training session before you start paddling. Once you start, you can go at your own pace.

Rent a kayak at Monroe Harbor (to paddle in the lake) or the Chicago Riverwalk (for the river). You can either paddle the lake or river independently or take part in a guided tour. Options include the historic tour, twilight paddle, fireworks tour, and sunset tour.

Be sure to make online reservations in advance, as you won’t be able to rent a kayak without them.

📚 Related Reading: Want to be sure you have everything you need for these outdoor experiences in Chicago? Our Chicago packing list may be helpful!

Mercury Cruises

A chance to enjoy Chicago cruising in a variety of family-friendly ways.

  • ⌚ Length: 1.5 – 2 Hours
  • 🌟 Guest Reviews: 4.5/5 Stars
  • 🗺️ Highlights: Sailing, Chicago buildings
  • ✅ Includes: Tour guide, varied amenities
  • 👉 Check prices & availability here

The most popular of the many family-friendly options offered by Mercury is the Urban Adventure Cruise on the river and lake. You’ll learn from the fun historical narration of the city as you look at the majestic buildings. These include the Aon Center and John Hancock Building, among others. 

The 3D Fireworks Cruise is an experience like no other. See not only the nighttime skyline of Chicago but also a rare view of the Navy Pier firework show with 3D glasses.

A great option for dog lovers is the Canine Cruise! Bring your dog, where they can enjoy safe outdoor seating and all the water they need. This also includes a narration of the city’s historical landscape but with an emphasis on the dog-friendly parts.

👉 Pro Tip: Want to do a self-guided tour? You can rent an electric boat or take a Chicago water taxi! Free Spirit Yacht Cruises is a good option for those with deep pockets – and you can also hire a tour guide to customize the experience.


Thank you for reading my guide to the best Chicago boat tours! Be sure to check out our list of the best Chicago restaurants before you go! Enjoy the water of the Windy City!

(Featured Image Credit: C.K. Photo / Shutterstock)

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