We used to live in Chicago and went back to show the city to our teenage children. The architectural boat tour was a great start to introduce them to the architectural landscape and history of our beloved city. […] The captain of the boat was a lot of fun and our tour guide was very knowledgeable. I studied the architecture of Chicago in college and she knew her facts.

Close Out Summer with a Chicago Labor Day Cruise on the River
Spend your Labor Day weekend enjoying one of Chicago’s most unforgettable experiences: a scenic Labor Day cruise along the iconic Chicago River. Our guided 90-minute Chicago River architecture cruise explores all three branches of the river, showcasing world-famous landmarks while our knowledgeable guides share the stories, history, and engineering that shaped the city’s remarkable skyline.
Whether you’re planning a holiday outing with family and friends or visiting the city in search of the best things to do over Labor Day weekend, this Labor Day weekend cruise offers the perfect mix of sightseeing, relaxation, and breathtaking views. Celebrate the holiday from the best seat in Chicago as you take in the skyline from the water.

Why a Boat Tour Is the Best Way to Spend Labor Day in Chicago
Labor Day weekend is one of the most exciting times to experience the Chicago River. As boats fill the water and visitors gather along the Riverwalk, a Chicago Labor Day cruise offers a front-row seat to the city’s iconic skyline without the crowds on land. Our 90-minute Chicago River architecture boat tour travels all three branches of the river, giving you more time to admire legendary landmarks, discover the stories behind them, and celebrate the unofficial end of summer from the best vantage point in the city.
With Tours & Boats, you’ll enjoy:
- A full 90 minutes on the river, the longest architecture cruise in Chicago
- Expert narration from guides who know Chicago’s buildings, history, and stories inside and out
- Open-air and enclosed decks so you can soak up the holiday sun or find shade
- A full-service bar on board with drinks and light snacks
- 360° river views with no obstructed sightlines
- A centrally located dock at River City Marina, 900 S Wells St, easy to reach from anywhere in the city
- Convenient nearby parking for those driving in for the holiday
Why Choose Tours & Boats for Your Labor Day Cruise?
Make your Labor Day weekend more memorable with a Chicago River architecture cruise that goes beyond the ordinary.
- The Longest Tour in Chicago. A full 90 minutes covering all three branches of the Chicago River.
- Expert Storytellers. Our guides bring the stories behind Chicago’s famous buildings to life: the architects, the eras, the fires and floods and reinventions that made Chicago what it is today.
- The Summer of George. Our signature vessel has both open-air and climate-controlled enclosed decks, 360° views, restrooms on board, and a full-service bar. Comfort built for a summer day on the water.
- Trusted by Thousands. More than 15,000 five-star reviews from guests who’ve experienced Chicago from the water.
Join us for an unforgettable Chicago Labor Day cruise.
Bring Your Group Together This Labor Day Weekend
Looking for a Labor Day weekend cruise everyone will enjoy? Skip the crowded attractions and spend 90 minutes cruising the Chicago River with expert narration, skyline views, and plenty of room to relax.
Whether you’re organizing a family gathering, a group of friends, or a company celebration, groups of six or more qualify for special discounts. Our centrally located dock at River City Marina is easy to reach by car, rideshare, or charter bus.
Hear from Our Previous Guests
From first-time visitors to lifelong Chicagoans, our guests love seeing the city from the water. Read their reviews and discover why so many recommend Tours & Boats.
We had a great informational time on the tour. So many buildings, so little time! Even at 90 minutes the tour seemed to fly by. Our guide, Sean, did a great job keeping the same pace as the boat describing each building in great detail, builders, architects, year, styles, and revisions.
Absolutely terrific river tour of Chicago’s architecture. When the other architectural tours were full, we defaulted to this one. HOME RUN! Billy was a wonderful guide. Obviously comfortable in front of a crowd, and his spontaneity kept us entertained throughout.
I have wanted to book this boat tour for years! I had family in town from England as well as out of state so I figured this would be perfect for everyone to see as much as possible with such a big group. It was perfect! We had so much fun!
Fun experience! The tour guide and captain of the ship were funny and engaging. The views is spectacular. I was born and raised in Chicago, but seeing it from the river at sunset was just spectacular. The route that was taken was incredibly scenic and I got some awesome shots of the city.
Book Your Chicago Labor Day Boat Cruise Today
Celebrate the unofficial end of summer aboard our 90-minute Chicago River architecture cruise. Secure your spot today!
Frequently Asked Questions
Do you run tours over Labor Day weekend?
Yes, we run our regular 90-minute Chicago architecture boat tours on Labor Day. Check our Eventbrite booking page for the current Labor Day departure schedule and to reserve your spot
What time do tours depart over Labor Day weekend?
Our Chicago Labor Day cruise operates with multiple departures throughout Labor Day weekend, giving you plenty of flexibility when planning your holiday. Visit our booking page for the latest schedule, available departure times, and to reserve your preferred Labor Day weekend cruise before tickets sell out.
How long is the Labor Day boat cruise?
Each cruise runs 90 minutes and covers the Main, North, and South branches of the Chicago River, with expert narration the entire way
What are the best things to do in Chicago over Labor Day weekend?
If you’re looking for memorable Labor Day activities, a Chicago River architecture boat tour should be at the top of your list. After your cruise, spend the rest of the day exploring nearby attractions like the Riverwalk, Navy Pier, Millennium Park, or one of Chicago’s famous baseball stadiums.
Is there food and drink on board?
Yes. The boat has a full-service bar with drinks and light snacks on board available for purchase. Outside food and beverages are not permitted.
Where do I board for the Labor Day cruise?
All tours depart from River City Marina at 900 S Wells St, Chicago, IL 60607. Plan to arrive at least 30 minutes before your departure time. Paid parking is available nearby.
Is the boat handicap accessible?
Unfortunately, the boat is not handicap accessible. There are about 15 to 20 steps that a person needs to climb up and down before entering the boat.
What happens if it rains over Labor Day weekend?
Our tours run rain or shine. The boat has a climate-controlled enclosed deck if the weather turns. Tours are only cancelled in cases of severe weather that affects safety, in which case we will contact you directly with rescheduling options.
Have More Questions? Visit our FAQ Page
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