The 3 Best Things To Do On The Chicago Waterfront

What’s an outdoorsy girl to do on a sunny summer day in a new city? Take to the water, of course!

The Chicago waterfront is both scenic and accessible, offering myriad activities and attractions on the water. My trip was MADE by the 3 B’s: bikes, beaches, and boats – aka the best things to do on the Chicago waterfront, according to Lindsay.

Lake Michigan in Chicago 

Biking Around Lake Michigan

In the past year, I’ve rented bikes while visiting Montreal, Washington DC, and San Francisco – so how could I not take to the pedals on my recent trip to Chicago?

I hired a Divvy Bike one day and immediately hit the waterfront. My first thought? Lake Michigan is absolutely ENORMOUS. With water as far as the eyes can see, it might as well have been an ocean in my mind.

My second thought? Man, biking around the waterfront is THE PERFECT late afternoon summer activity in Chicago. The Lakefront Trail winds for 18.5 miles through parks, beaches, tennis courts, picnic areas, and museums. Views of the water alternate with jaunts through the trees, the late day sun toasting your skin on one side. Absolutely glorious!

Chicago Waterfront
Lake Michigan in Chicago
Biking Around Lake Michigan in Chicago 

To Divvy or Not to Divvy?

With the temptation to make constant stops, I found the 30-minute ride limit of the Divvy Bike to be too short. There are plenty of stations along the way to swap out your bike and reset your 30 minutes, but you likely wouldn’t notice them unless you consulted a map because many are off the trail. I was constantly checking the time to see how close I was to the 30 minutes being up and was late at least once – definitely not ideal when embarking on a long, carefree ride.

If I were to bike Chicago’s Lakefront Trail again, I’d look into renting a bike by the hour or day instead. However, for shorter trips around the city – Divvy is clutch!

Biking Around Lake Michigan in Chicago 

Beaches in Chicago

For a city so notorious for its cold winter and, well, windy tendencies, you likely wouldn’t equate Chicago with beaches. But come June, Chicagoans flock to the lakefront for some quality time in the sand and sun. At some beaches on the Chicago waterfront you can even play volleyball or rent boats.

I thought the coolest thing was being able to walk up the landmark-studded Magnificent Mile and end up right on Oak Street Beach. It’s literally city skyline meets sand, something you don’t see too often.

Chicago Waterfront
Chicago Beach
Chicago Beach 

Boat Trip on the Chicago River

BlogHouse hooked me and my fellow bloggers up with a ride up the Chicago River with Chicago Electric Boat Company and it was easily one of, if not THE highlight of our time in the city. Captaining our own boats, we explored the Chicago River at a leisurely pace – taking in the glowing buildings up close and passing by bridge after bridge. And you KNOW how I feel about bridges!

Chicago E-Boats is great for groups that want to charter their own boat and have the freedom to roam around wherever they please, but for smaller parties and those who want to learn a bit about the buildings they’re passing by, one of Chicago’s famed architecture boat tours might be a better option.

Chicago River Boat Trip
Chicago River
Chicago River Boat Trip
Chicago River Boat Trip
Chicago River Boat Trip 

Which would you rather do on the Chicago waterfront: bike, beach, or boat?

Lindsay Buckley is the photographer and travel blogger behind Frugal Frolicker. She's a New Yorker currently based in Sydney, Australia, documenting outdoor travel experiences Down Under and beyond. Follow along with Lindsay's travel photography on Facebook and Instagram, and be sure to sign up for the monthly Frugal Frolicker newsletter!

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  • Beautiful Lindsay. I too loved the waterfront during the visit to Chicago! I also agree that the Divvy time limit was not so fun and I always had to find a way to quickly return the bike to make sure I didn’t get charged.

    • lindsaypunk

      Thanks, Chanel! We were so lucky with the weather there, too. And agreed – I’ve run into the time limit problem in different cities now. These commuter bikes are best when you want to get from A to B, no funny business. Doesn’t really jive w/ my frolicking style, ya know?

  • To Divvy or not to Divvy….SO GLAD you raised this question. My mom and I took Divvy bikes along the lakefront, and while the actual lakefront ride was a real highlight of the trip, the initial process of getting the bikes made me want to tear my hair out (several of the stations were broken, there were no slots to return them in the busiest area near Grant park, we needed two credit cards, etc.) Then, once on the lakefront, we were constantly consulting an iphone to find the next return station. If we did it again, we’d for sure rent all-day bikes from somewhere! That said, I think it’s a great service for locals who need it more for short commutes.

    • lindsaypunk

      OMG YES!! There were multiple stations that wouldn’t accept my card and it was a royal pain having to look up a nearby station on my phone and then hop over there and try it again. No idea why that kept happening. I actually didn’t have the full station issue in Chicago, but did when I used the commuter bike in DC earlier this year. It’s comforting to know it wasn’t just ME that Divvy was making life difficult for!

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