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Best Things to do on The Chicago Riverwalk

Local-approved ways to experience the Chicago River!

Ah the Chicago Riverwalk! There are few better places to be on a bright Chicago afternoon or warm summer evening. I myself am always drawn to water whenever I travel, and my home city is no exception. It’s my favorite place to bring visitors, and an amazing place to spend my lunch breaks or to grab a bite after work. There’s usually a nice breeze coming in off the lake, and the views absolutely cannot be beat.

So, without further ado, here are my local-approved recommendations for the best ways to experience the Chicago River:

#1 - Book a River Cruise

view of the Chicago River from a small boat

Sometimes the top-rated attraction is just a trap set up to get those tourist dollars. Other times, it’s the top attraction because it’s actually the best thing to do in the city. Never has this been more true than of the Architecture Cruises at Wendella Tours.

Chicago is absolutely bursting with unique architecture, and there is no better way to see the highlights than from the water. The boats at Wendella Tours are large and comfortable, with huge sun decks and a climate-controlled lower level. They offer 45-minute and 90-minute architecture cruises, as well as a long list of additional scenic offerings. The architecture cruises are my favorite because of the unique history lessons you get from your tour guide along the route. You don’t have to be an architecture buff to enjoy learning about the city and its buildings. It’s truly an interesting and beautiful experience for everyone. (Though please ask me about the time I chaperoned a group of two dozen drunk architects on one of these tours!)

There are many different companies that offer river cruises, but I can personally vouch for the excellence of the experience with Wendella. Plus, they’re very conveniently located with docks right on Michigan Avenue, and their boats depart dozens of times a day, rain or shine! It’s truly a must-do on any visit to Chicago.

#2 - Go for a Paddle

For the adventurous types who want to get up close and personal with the river, try out some urban kayaking with Wateriders! Waterriders offers a wide array of tours, and also offers rentals if you want to explore the water on your own.

I’ve been on many tours with Wateriders, and I truly cannot recommend them enough. They offer a History and Architecture paddle, where you’ll stop periodically and “raft up” to listen to your guide tell stories about the city before paddling to the next location. For a more eerie experience, you can book a Ghosts and Gangsters tour, where the stories will involve hauntings and mobsters. Or if storytelling isn’t your jam, you can book a scenic paddle and call it a day. Every tour, regardless of genre, starts with a paddling lesson, and you’re never without your experienced guides.

a kayaker on the Chicago River

As an additional note, there are multiple urban kayaking companies that call the Chicago River home, and I have found Wateriders to be the vastly superior company. Kayaking with Wateriders is quite possibly my favorite thing to do on the Chicago River. It’s a one-of-a-kind experience that should not be missed.

#3 - Grab a Bite

Now that you’ve worked up an appetite on your tour (especially if you paddled it yourself!), it’s time for a bite to eat. The south shore of the Chicago River is a smorgasbord of excellent restaurants, all of which have an amazing view of the water. I especially love grabbing a table near the riverside and watching the sun go down. The sight of the sunset against the river and the buildings is truly something else!

the Chicago River and the Wrigley Building at night

There are tons of restaurants to choose from (I’ll give you a full list in a moment), but I want to call out my personal favorite: The Northman on the Riverwalk. The photo here is the view from their patio at night. This establishment is a cider bar with a myriad of drink options (read: not just cider) and creative bohemian food. I love a good hard cider, and the Northman’s house Pub Cider is what

dreams are made of. They also serve what might be the best Chicago-style hot dog in the city, and I’m a huge fan of their flavorful curried chicken salad sandwich. If you’re visiting in the summer, odds are high that there will be live music under their shelter as well!

But if I haven’t sold you on the Northman yet, here’s a few more options for you to check out:

Chicago Brewhouse: A full bar focusing on local drafts, and upscale pub classics

City Winery: A riverside wine bar with sandwiches and small plates

Tiny Tapp: Café with a wide variety of food and a full bar, as well as

specialty coffee drinks and ice cream

#4 - Go Find some Strange Art!

For some wild, one-of-a-kind public art, wander down past the Merchandise Mart building and appreciate the beautiful digital weirdness of Art on the Mart. This attraction is only available after the sun starts to go down and the moving digital projections become visible. The art on display changes regularly, so you’re never quite going to be sure what you’ll see. But as the world’s largest digital art platform, Art on the Mart is truly something you can’t see anywhere else.

#5 - Get a View of the Chicago Riverwalk from Above

A woman and a child enjoying drinks and snacks on a rooftop bar in Chicago
(Sidebar, this is not my kid. This is me being a top-notch role model for my niece)

Last but certainly not least, the one view of the river you haven’t gotten yet is a view from above it. And for that view, there is no place I recommend more highly than the rooftop bar at the LondonHouse hotel.

Located right across from the south bank and just off Michigan Avenue, the LondonHouse has the perfect view of the river and its neighboring buildings. It’s rooftop restaurant and bar have been voted among the best of Chicago on many occasions.

If you want to eat at the restaurant, you absolutely need a reservation. They fill up

quickly, so book as far in advance as you can. If you just want a drink and to soak in the views (which is what I recommend,

tbh), you don’t need a reservation, but you may need to wait in line a bit for the elevator. (Unless you happen to be staying at the LondonHouse, you lucky bastard, in which case you can skip the line!)

And once you’re up there, the view over the river and the exquisite drinks are worth the wait. There’s no better river view in the city.

And there you are! A choose your own adventure guide for the Chicago River. Whether you see the river by boat, kayak, or from the walkways and restaurants on its banks, there’s always going to be a way to enjoy the river that’s just right for you.

Want to know how these highlights might fit into a weekend itinerary for the Windy City? Good I thing I made one for you! You can check it out right HERE!

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Love and Shenanigans,


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