Sightseeing Cruises

90-min Chicago River and Lake Michigan Architecture Cruise

Chicago River with skyline view, featuring modern skyscrapers on a 45min architecture cruise.

Chicago skyline with Willis Tower viewed from the river, featuring a raised railway bridge.

Chicago skyline with boats on the river during architecture cruise.

Duration

1 hr 30 min

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Guided tour

Do more than just a standard Chicago River cruise, & sail onto Lake Michigan for a comprehensive exploration of Chicago's skyline. Operator: Wendella

4.7/5

(51)

Connie

Sep 2025

Verified booking

5/5

We had such a wonderful time on the Chicago River architecture Cruise experiencing the city from the water, gave us a whole new perspective, and the views were absolutely stunning. The guide was knowledgeable, engaging, and made the history of the building's came to life with fun facts and stories. It was a perfect outing for family and friends, relaxing, scenic, and full of wow moments as we cruise past Chicago's iconic skyline. The boat was comfortable, clean and easy to move around for taking photos. Everyone in our group from kids to adults really enjoyed it. I'd highly recommend this Cruise to anyone visiting Chicago or even locals who want to see their city in a new light. It's a must do experience.

Traci

Oct 2025

Verified booking

5/5

The tour guide was exceptional - highly knowledgeable, very engaging, and personable for the entire 90 minutes. I wasn't expecting to laugh as much as I did - but he kept the mood light throughout! We did the River/Lake Michigan tour and the additional history and geographical context that was shared was a highlight for me! Highly recommend the 90 minute tour!

Susan

Sep 2025

Verified booking

5/5

I highly recommend this cruise for anyone visiting the city. The crew were very professional and our guide was informative and extremely personable. Ken held our attention for the entire cruise.

Enjoy a 90-min guided boat tour on the Chicago River and one of the five Great Lakes, Lake Michigan, with skip-the-line entry.

Take in the city’s famous skyline and architectural icons from both the river and lake while relaxing indoors or on open-air decks.

Learn how Chicago’s skyline came to life with engaging narration as you cruise past historic buildings and modern skyscrapers.

This extended cruise offers more than standard river tours, covering additional landmarks and panoramic lakefront city views.

Perfect for first-time visitors, architecture buffs, and photography enthusiasts looking to explore Chicago from a different perspective."

90-min architecture cruise

Boat cruise on Chicago River & Lake Michigan

English-speaking tour guide

Food and drinks (Available for purchase on board)

TOTAL DURATION90 minutes
FREQUENCYOnce per day
FIRST DEPARTUREChicago Harbor Lock
LAST DEPARTUREChicago Harbor Lock
1 Boarding point
Wendella's Michigan Avenue Docks
Get direction
Sights covered
Chicago Harbor Lock
Navy Pier
Oak Street Beach
Chicago Lighthouse
Museum Campus
Buckingham Fountain

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

4.7
51 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from France, Germany, United Kingdom and over 6 countries have loved this experience
What our guests say
Suryanarayana
Oct 2025
Verified booking
5/5
I absolutely loved my experience on the Wendella Chicago River Architecture Cruise! The tour was both relaxing and educational, offering an incredible perspective of Chicago’s iconic skyline and its rich architectural history. Cruising through the river gave me a completely different appreciation of the city’s design — from the classic art deco buildings to the stunning modern skyscrapers. What I enjoyed the most was seeing the downtown view open up as we entered Lake Michigan — the panoramic view from the water was breathtaking. The guide was knowledgeable and engaging, making the entire journey both fun and insightful. A truly memorable Chicago experience!
Traci
Oct 2025
Verified booking
5/5
The tour guide was exceptional - highly knowledgeable, very engaging, and personable for the entire 90 minutes. I wasn't expecting to laugh as much as I did - but he kept the mood light throughout! We did the River/Lake Michigan tour and the additional history and geographical context that was shared was a highlight for me! Highly recommend the 90 minute tour!
Tyler
Oct 2025
Verified booking
5/5
Such a great trip and vantage point of the city. We stood at the back of the boat on the bottom deck and had unobstructed views the entire time!
Amanda
Oct 2025
Verified booking
5/5
Highly recommend this experience! Alex was superb learnt so much about this beautiful city in such a short amount of time..
Willie
Oct 2025
Verified booking
5/5
The tour guide host was super funny! The weather was perfect what more could you ask for

Experience Chicago’s iconic skyline

The 90-min Chicago River and Lake Michigan Architecture Cruise offers a unique dual-perspective journey, showcasing the city's most renowned skyscrapers and historic buildings from both the river and the lake. Unlike standard river tours, this extended cruise includes a stretch onto Lake Michigan, delivering panoramic views of the entire skyline and allowing for exceptional photo opportunities. Navigate through the heart of Chicago via the Chicago River, passing beneath iconic bridges and right alongside legendary structures like the Wrigley Building and Willis Tower.

Expert-led architectural insights

Knowledgeable guides provide engaging commentary throughout the cruise, offering fascinating stories and historical context behind Chicago’s architectural evolution—from early 20th-century landmarks to cutting-edge modern designs. This cruise is an ideal introduction to the city’s rich design heritage and urban beauty, blending sightseeing with educational value in a relaxed, scenic setting.

What's not allowed

Alcohol, weapons of any kind, flammables, and explosives are not allowed on this experience.

Smoking cigarettes (including e-cigarettes) is prohibited on board.

Accessibility

This experience is wheelchair and pram/stroller accessible.

Your guide dogs are welcome on board the boat.

Additional information

The Captain may adjust the tour route as needed to ensure the safety and comfort of all passengers.

Safety comes first. All bags are subject to inspection.

The crew reserves the right to deny entry to anyone who appears intoxicated, impaired, or may pose a safety risk.

Your voucher will be emailed to you instantly.

Display the voucher on your mobile phone with a valid photo ID at the meeting point.

Please arrive at the meeting point 15 mins before the scheduled time of your tour to avoid any delays.

Meeting point

Meet your guide at Wendella Tours & Cruises.

Address: 400 N Michigan Ave, Chicago, IL 60611, United States.

Landmark: The dock is located at the northwest corner of the Michigan Avenue Bridge (now called the DuSable Bridge), at the base of the Wrigley Building on the Chicago River.

Get directions to the meeting point