Updated July 31, 2023
A major highlight of your trip to the Windy City during the spring to fall seasons is certainly a tour of the Chicago River on a cruise boat. Not only will you have the best vantage point to appreciate the Windy City’s spectacular architecture, but you will also get a good perspective of the landscape of the city and their positions relative to the three branches of the waterway.
The term “River North”, which refers to the district of lively dining and nightlife scenes, finally begins to make sense. If you are staying for at least a few days, I recommend you take this cruise on the first or second day to get a good orientation of the city, which might help you find your way around town for the remaining of your trip.
One of the most popular sightseeing excursions is the Chicago Architecture River Cruise by Shoreline Sightseeing. I took this cruise twice and am completely satisfied. I am ready to do it again soon!
The advantages of going with Shoreline are that their boats are large, spacious, comfortable, and equipped with clean bathrooms. There is a full bar that sells ice cold beers, a wide variety of cocktails, as well as soft drinks. Both times that I was there, the bartender was super nice and friendly.
TIP: Once the boat sets sail the bar gets crowded very quickly so you might end up standing in line at the bar instead of enjoying a good part of the journey. If you would like to purchase a drink, my tip for you is to board early and get your drinks right away while the line at the bar is still short.
The company operates many boats and schedules over 20 sailings a day which give you plenty of flexibility to your itinerary. You have a choice of two departure points: Navy Pier or Michigan Avenue. Navy Pier – home to the iconic Centennial Wheel – is a dining, entertainment, and tourist destination by itself, so it is a naturally convenient location. The Michigan Avenue departure point is great if you stay near the area, or plan on visiting the Magnificent Mile before or after the tour.
Once the journey begins, you will find yourself navigating through a maze of stunning skyscrapers. Another reason that I really enjoy the architecture boat tour is that the guides are very knowledgeable, and they deliver an interactive and informative commentary punctuated with humor and funny tidbits.
The guides will give you detailed background on many noteworthy structures including both historical and technological aspects of their design and construction. Nowhere else could you find such a rich and comprehensive presentation of the majestic architecture of Chicago in just a little over an hour while enjoying a river boat tour (and sipping cocktails, too!)
If your starting point is Navy Pier, you will first be heading west. To your right is the area known as River North. You will be sailing under a series of bridges, each of which is a major highway. For example, the DuSable Bridge is the part of Michigan Avenue that crosses over the waterway. The picture above shows the boat going under the bridge that is State Street.
There is no shortage of skyscrapers along the way. The two most famous ones are of course John Hancock Center and Willis Tower (many locals still call it Sears Tower). Your guide will give you the background of the 110-story skyscraper that the then-retail giant Sears Roebuck & Company built as their headquarters. You will learn about the technology that was developed specifically for this structure to enable it to withstand both wind and gravity.
There is also no shortage of unique and bold designs either, such as the 400-foot-tall mural painted on the office building at 300 South Wacker Drive, which portrays a map of Chicago River. The building itself is depicted by a red rectangular box on the map. As you pass by the building, the rectangular box also represents your position in the river at that moment.
There is also no shortage of gigantic buildings. The MART (previously known as the Merchandise Mart) was once the largest building in the World when it was built in the 1930’s. Its Art Deco style was predominant in the 1920’s and 1930’s, and the building graces the Chicago architectural scene with its historical design. The MART is so big that it covers two city blocks and has its own zip code.
One of my favorite scenes of the tour is the Riverwalk. From late spring to early fall, this one and a quarter mile stretch of parks, promenades, restaurants, and bars is always a vibrant but also relaxing place to hang out.
Seeing the Riverwalk from your boat gives you a completely different perspective of the scenery. This also reminded me of the many faces of the city that we passed through during the cruise which could only be seen from the waterway where we sailed along. This is a viewpoint of the city that you cannot see on foot or by car.
Depending on the day and the season, you may also be accompanied by a dozen or two of canoes or kayaks. On a side note, there is actually a kayak rental company in the neighborhood and if you feel like being adventurous on a beautiful summer day, that might be a great thing to do after the excursion.
Overall, I really enjoyed my experience on the Chicago Architecture River Cruise, and I found the boat tour relaxing, entertaining, as well as educational. This excursion includes over 40 signature structures of the Windy City, many of which are famous landmarks. You’ll get to see the city’s stunning skyline from the best vantage point and soak up all the background information on their constructions. I really appreciated the presence of a knowledgeable tour guide and a commentary that is interactive. Maybe it’s just me, but I do not prefer those tours with pre-recorded commentary delivered through earbuds. The cruise is one hour and 15 minutes long, and believe me, you will enjoy every moment of it.