One of my favorite things about Chicago is its skyline. Its architecture feels so different from many other American cities and taking in the architecture from different angles is one of the best things you can do on your visit. Yes, you can wander the through the Chicago Loop and look up, but you can take your sightseeing to the next level by getting out on the water. The Chicago River cuts through the city, eventually emptying out in Lake Michigan, and makes a great spine four touring.
In this guide, I’ll give you several options for how you can explore the Chicago architecture via the river.
Chicago Riverwalk
The first option I’m going to cover is the easiest and cheapest. But in my opinion, it can be worst way to explore the river. A 1.25 mile pedestrian path follows the Chicago River from Lake Street and Wacker Drive, all the way out to Lake Michigan.
Now, I said this is the worst way to explore the river, but I do think it’s worth it in a few scenarios. I typically visit Chicago in December and quite frankly, it’s cold. However, if you visit in summer, I’d actually recommend stopping here. Yes you’ll find the pedestrian path, so you can go for a stroll, but you’ll also find restaurants and bars. When I visited in August with my family, we came down here for pre-dinner drinks and it was a nice experience. If you’re here in winter, all of this is closed because as I mentioned: it’s cold!
Chicago Sightseeing Boats
The second option is the Chicago Sightseeing Boats, which is another easy option, but it does come with a cost. Many tourists who select this option do so via one of the Architecture Boat Tours. These tours are affordable, packed with information, and are the most convenient way to get out on the water.
So what’s the tour like?
I took the Architecture Boat Tour with Wendella on my 2021 trip to Chicago. The tour itself lasted about an hour and a half hours and provided live commentary for most of the duration. The views were fantastic and the information was great—when we could hear it. I don’t know if it was just the day we went, the sound system for the boat we had, or the guide, but I found myself having to give all of my focus to our guide in order to make out what was being said. That said, our guide was super passionate about Chicago history and was a fountain of knowledge. And the views from the boat were just incredible.
The tour started near the DuSable Bridge. We headed west, turned around, then came all the way back (passed our boarding point) and out to Lake Michigan. From Lake Michigan, we turned around and they gave us a few extra minutes here. This is where you’ll get a great view of the Chicago skyline. From Lake Michigan, it was back to our starting point.
If you’re interested in the architecture tour, know that you can do it all year round. Yes, even in winter. I actually took the tour in December. Yes, it was cold, but I still think it was absolutely worth it (although I’d recommend going in a warmer month if you have the option).
Boat Rental
The next option is a boat rental. This allows you to get those magnificent views of the architecture from the Chicago River, but gives you some more privacy. There’s plenty of rental options, from small electric boats to larger yachts and everything in between.
The benefit of a boat rental is you can go where you want (within reason) at your own pace. The sightseeing boats have a designated schedule and tour so you may be limited where you can see.
And for people who are unsure about driving a boat down the river, for an additional fee, you can hire a captain to drive you. While more expensive, with an experienced captain, they’ll take you to all the best places. Plus everyone on your boat can enjoy the scenery (and a drink). The captain takes care of all of the difficult parts so you can enjoy the night.
The additional added benefit of a captain is that they know the area. A captain will know the spots for the best views and where to avoid crowds of boats. My dad would also like to point out that if you have a captain, there’s the another bonus of them having to dodge all of the kayakers, so you don’t have to pay attention to them (because in summer the river is full of kayakers!).
My family and I rented a boat in the summer of 2023 and it was a fabulous experience. We opted to do our tour at night, with the city lights all around us. It was beautiful! Our plan was to make our way out to Lake Michigan to watch the summer fireworks, but due to some crazy winds, we didn’t make it (plus the fireworks weren’t shot off that night). 10/10, we would definitely do it again. Although, Dad, if you’re reading this, next time let’s use Chris’s boat 🙂
Rent a Kayak
My fourth and final option is a kayak rental. This is the only option on this list that I haven’t done, but kayaking is now a very popular way to explore the Chicago River. With a kayak rental, you get the great city views, but also get some exercise.
If you choose to rent a kayak to explore, please be careful. Especially in summer, the Chicago River is full with other boaters, tour groups, and even other kayakers. You need to be aware of your surroundings.
When to Do This
Technically all of these options are available all year round. I’ve been on the Chicago Riverwalk and took the Architecture Boat Tour in winter. Yes it was cold, but it was still gorgeous because of the amazing views. And, if you’re on the water in winter, you have a great excuse to get coffee or hot chocolate after your tour!
However, if you want a better experience, I’d recommend late spring, summer, or early fall. Summers will be the busiest, but that’s when the weather is the best. It can be hot and what better way to beat the heat than on a boat.
As far as a time of day, the choice is yours. I did the Architecture Boat Tour during the day, but I did a private boat rental at night. Both had great views, but I will say, photos are a lot easier to take during the day than at night.
Continue Your Adventure
Chicago: For more in Chicago, check out my list of the Best Things to Do in Chicago.
Indiana Dunes: It’s outside of Chicago (and Illinois), but Indiana Dunes National Park is nearby. There’s even a hike that gives you a view of the Chicago Skyline.
St. Louis: It’s a five hour drive, but you can add St. Louis as a road trip stop.