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Chicago’s Best Architecture River Cruise: Perfect for the First-Time Visitor

Traveling has always been one of my passions. It exposes us to new cultures and experiences and makes the world a more tolerant place.


Anyone who has visited the Windy City knows full well that Chicago is home to a fascinating variety of architectural styles. It is what helps make Chicago one of the most interesting and diverse cities in America. And while you can certainly appreciate the vision and workmanship that went into each building while walking the city, there is a unique and much more entertaining way to learn about Chicago’s architectural history.

The Chicago Architecture Center River Cruise, aboard one of Chicago’s First Lady vessels, is the ideal way to see the city and hear the story behind each of these historic landmark buildings.

Chicago’s Fair Lady

Chicago’s Fair Lady

Chicago Architecture Center

The Chicago Architecture Center was formed in 1966 and began offering river cruises in 1983. In 2018 the center moved into its new home located at 111 E. Wacker Drive and continues its mission of promoting and preserving the architectural legacy of Chicago.

In 1993 Chicago’s First Lady fleet was born, and her boats have cruised the Chicago River to the delight of visitors for over 25 years now. Since that time hundreds of thousands of visitors have had the opportunity to experience the magic of Chicago from the comfort of the First Lady fleet. With a spacious open-air upper deck in addition to the enclosed climate-controlled lower deck, the boats can accommodate up to 250 passengers. There is also a full-service bar and restroom facilities to make this a comfortable experience.

Navy Pier

Navy Pier

Docents Make a Difference

What really separates this tour from other similar tours is the expert team of docents that have been assembled to lead the tours. For our cruise, we had the pleasure of having Kathleen educate us on everything that is Chicago. The docents are all volunteers, and they come from a variety of backgrounds and careers. What they all share is a love and passion for Chicago and its unique architecture.

Docents are carefully selected and trained to serve as educators and ambassadors for the city of Chicago. We found our docent, Kathleen, to be an amazing source of information on almost every building in the city, and her tone and pace during the tour were exceptional.

The Merchandise Mart Building

The Merchandise Mart Building

The Sunset Cruise

Cruises depart daily starting at 9:00 am with many departure times throughout the day. The Sunset Cruise departs each evening at 7:30 pm and all cruises last for about an hour and a half. Sunset cruises are only available from May 17th until October 14th.

I highly recommend the Sunset Cruise, as you get to see the city at twilight and then after sunset when the buildings are all lit up. The reflection of the lights on the river combined with the beautiful way that many of the buildings are illuminated at night makes for a stunning setting. Be sure to bring your camera as this tour will provide ample photo opportunities.

The Jewelers Building - 35 East Wacker Drive

The Jewelers Building - 35 East Wacker Drive

As your cruise departs, your docent will begin to tell you the history of the buildings surrounding you. Prominently displayed before you as the tour begins is the historic Wrigley Building. Constructed in 1920 as the headquarters of the Wrigley Chewing Gum Company, this is one of Chicago’s most striking and unique buildings. It was the first office building in Chicago to have air-conditioning and its unique clock tower was designed to resemble the famous Giralda Tower of Seville’s Cathedral in Spain. This was just the beginning of what turned out to be a fascinating 90-minute tour.

Wrigley Building

Wrigley Building

What to Expect

While I won’t get into the details of every building that we saw, I can tell you that you will have the opportunity to see and hear the story behind the most famous buildings that grace the Chicago skyline. The tour will include the Willis Tower (still Chicago’s tallest building), Navy Pier, the Tribune Tower, the Lyric Opera building, Marina City, the huge Merchandise Mart building, and virtually every other building of significance in the city.

It really was fascinating to learn about the many different architectural styles, and by the time your tour ends, you will have been educated on up to 50 of the most important buildings, bridges, and parks in Chicago. From the gravity-defying design of 150 North Riverside to the award-winning Aqua Tower, it was amazing to learn how Chicago has become one of the most innovative and architecturally progressive cities in the world. To be honest, prior to visiting Chicago I had no idea that some of the most famous architects in the world hail from the Windy City.

Willis Tower - Chicago's tallest building

Willis Tower - Chicago's tallest building

150 North Riverside Building

150 North Riverside Building

Of all the buildings that we saw during our river cruise, I think the Wrigley Building was easily my favorite. Between its history, the clock tower, its early 20th-century design, and the terra-cotta exterior, it really appealed to me. It stands out from the gleaming glass and metal exterior of many of the other more modern buildings, and its place right on the Chicago River is the perfect setting.

The Historic Wrigley Building

The Historic Wrigley Building

River Cruise Information

  • Daytime river cruise: $46.29 plus tax
  • Twilight cruise: $51.02 plus tax
  • Duration: 90 minutes
  • Departures start at 9 am and leave every 30 minutes throughout the day.
  • Sunset cruise departs at 7:30 pm.
  • Chicago’s First Lady fleet consists of six boats: the Little Lady, Fair Lady, First Lady, Leading Lady, Classic Lady, and the Lady Grebe.
  • Tours are rain or shine.
  • You can visit the CAC (Chicago Architecture Center) for just an extra $5. This saves $7 off the regular $12 admission price.
  • All seating is general admission, but don’t worry as there is not a bad seat on the upper deck for viewing.
  • Tours sell out often so advanced ticket purchase is highly recommended. You can buy tickets on the CAC website.
  • Snacks and beverages are available on board for purchase. You can also bring your own snacks/food with you.


The departure point for the boat tour is along the River Walk at the Michigan Avenue Bridge (also known as the DuSable Bridge) at Wacker Drive. There is a blue awning that marks the entrance to a stairway that will take you down to the River Walk. You should plan on arriving about 30 minutes before your departure time as they start boarding 15 minutes prior to departing.

Michigan Avenue Bridge also known as the DuSable Bridge

Michigan Avenue Bridge also known as the DuSable Bridge

If you want to learn about the history of Chicago and have an interest in different architectural styles, then this is the perfect way to get an overview of the city. I think that this tour would be ideal for any first-time visitor to Chicago. While we have flown through Chicago numerous times, this was actually our first visit to the Windy City and this Sunset Cruise was definitely the highlight of our visit.

The Apple Store (notice the shape of the roof) with the Chicago Tribune behind

The Apple Store (notice the shape of the roof) with the Chicago Tribune behind

Questions & Answers

Question: Are there any dinner cruises on the Chicago River?

Answer: Yes, there are a number of companies that offer both river and lake dinner cruises. The Chicago Architecture Center only offers architecture cruises, but a quick Google search will show many companies that offer dinner cruises. We noticed a number of them while on our cruise up the Chicago River.

© 2019 Bill De Giulio


Bill De Giulio (author) from Massachusetts on March 29, 2020:

It really was a great way to see the city, especially for first-time visitors. We would definitely go again if we return to Chicago. Have a great day.

Peggy Woods from Houston, Texas on March 29, 2020:

I see from reading your article that these architecture river cruises began in 1983. We used to spend quite a bit of time visiting Chicago when my husband and I lived in central Wisconsin back in the 1970s. We would have liked taking one of these cruises had they been available. Thanks for informing us about them.

Bill De Giulio (author) from Massachusetts on June 05, 2019:

Thank you Mary. We really enjoyed the tour and it definitely was an education. Have a great day.

Mary Norton from Ontario, Canada on June 04, 2019:

What an interesting tour and for that price, what an education!

Bill De Giulio (author) from Massachusetts on June 04, 2019:

Thank you Liz. It was a great way to see the city from a different perspective. Kathleen, the docent who was our guide was excellent, and really gave a great commentary on the history of Chicago.

Liz Westwood from UK on June 04, 2019:

You have definitely sold this cruise to me. It sounds fascinating. We often like to take to the water when sightseeing in a new city. It offers respite to the footsore tourist and the opportunity to view the city from a different perspective. If there's an excellent and informative commentary as well it ticks all the boxes.

Bill De Giulio (author) from Massachusetts on June 03, 2019:

Thank you Flourish. It was fun, and a great way to learn about the history of Chicago. We would even do it again if we return. Have a great day.

FlourishAnyway from USA on June 02, 2019:

I’ve been to Chicago a number of times but never done the tourist thing and really should have. Next time I will! Beautiful photos! Seems like a lot of fun.

Bill De Giulio (author) from Massachusetts on June 02, 2019:

Thank you Gupi. Glad you enjoyed it. Have a great day.

Gupi on June 02, 2019:

Very interesting and well structured article

Bill De Giulio (author) from Massachusetts on June 02, 2019:

Thank you James. It was a great way to see the city and learn the history of Chicago. We really enjoyed it. This was our first visit to Chicago and I can definitely see us going back soon. Have a great day.

James A Watkins from Chicago on June 02, 2019:

Thank you for this very interesting article. I haven't been on this cruise but my wife has and she says it is fun. I enjoyed your fine, crisp writing.

Bill De Giulio (author) from Massachusetts on June 02, 2019:

Thank you Heidi. I must say we really enjoyed Chicago. Great city with so much to see and do. We actually went to the Blommer Chocolate Factory the day after the cruise. We loved the boat tour, great way to see the city. Have a great day.

Heidi Thorne from Chicago Area on June 02, 2019:

Wow, such beautiful photos of my sweet home Chicago! If you came here in May, glad you got to go on the tour on the few non-rain days we had (rainiest May on record).

We went on the Wendella boat tour a year or two ago, that had the architecture tour, going through the locks and then out onto Lake Michigan. I can recommend that one, too.

And, yes, the Blommer Chocolate Factory truly does make it "sweet" home Chicago. I used to work downtown and the bus used to pass right by it. The aroma is incredible.

Thanks for showcasing my beautiful town (even though I'm now in the 'burbs)!

Bill De Giulio (author) from Massachusetts on June 01, 2019:

Thank you Brian. The Aqua Building was one of the more unique buildings we saw on the cruise. Great way to see the city and learn the history behind it. We would definitely do it again also. Have a great day.

Bill De Giulio (author) from Massachusetts on June 01, 2019:

Thank you Linda. We found it to be a great way to see the city and learn the history of Chicago. Our docent did an excellent job. Have a great weekend.

Brian Lokker from Bethesda, Maryland on June 01, 2019:

Very good guide, Bill. I took the tour on the Chicago Lady in August 2017 and thoroughly enjoyed it, both for the architecture and the history lesson. The variety of the buildings is impressive. I'd have to say my favorite is the Aqua with the rippling effect caused by its undulating balconies. Interesting too that it is (or at least was when it opened) the largest American building project headed by a woman (Jeanna Gang). I would take the tour again on another visit to Chicago.

Linda Crampton from British Columbia, Canada on June 01, 2019:

I've never been to Chicago. I like the idea of exploring the city by taking a river cruise very much. Looking at the architecture of the buildings is one of my favorite activities when I visit a city. If I ever go to Chicago, I'll definitely take the cruise that you've described.

Bill De Giulio (author) from Massachusetts on June 01, 2019:

Thanks, Bill. I could never live in a big city, but I do enjoy visiting them for a few days at a time. Chicago really surprised us, very clean, very walkable, and lots of interesting food. A great weekend to you also.

Bill De Giulio (author) from Massachusetts on June 01, 2019:

Thank you Pam. We really enjoyed Chicago and this river cruise was definitely a highlight for us. I’m not sure I would enjoy winter there, but for a nice spring long weekend visit it was wonderful.

Bill Holland from Olympia, WA on June 01, 2019:

Me and big cities, buddy, that's just not workable. That makes your article very valuable to me. I didn't know Chicago had cruises....I learn something new every single day on HP. Thanks, Bill! Have a great weekend.

Pamela Oglesby from Sunny Florida on June 01, 2019:

This cruise not only sounds very informative, but so much fun. I also like various architecture. I have a grandson who recently moved to Chicago, and they love it there. I thought the cold weather would get to them, but not at all. I will tell him about the cruise when we talk again. This is a very interesting article.

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