One Of The Best Beaches In The Midwest Is This One-Of-A-Kind Urban Gem

One of the things people underestimate about Chicago is its incredible shoreline — not just Lake Michigan itself, but the gorgeous beaches that also line the city. One such beach was recognized in 2024 by Travel & Leisure as one of the best in the country: Oak Street Beach. Nestled against the Gold Coast and Streeterville neighborhoods, Oak Street is one of the most popular beaches in Chicago. Considering that there are 26 beaches in the city, that's no small feat. 

Even though this beach is hopping all summer long, it's even popular in the frigid Midwestern cold. That's because the Chicago Polar Bear Club holds their annual Polar Plunge from Oak Street each January to help Chicago families in need. There is even talk of making the beach bigger to help protect the nearby bike paths and Lake Shore Drive from water damage as the city's beaches erode.  

Though it's far from making any best undiscovered beaches lists, Oak Street is still a hidden gem in its own right. Anyone who hasn't been to a Chicago beach might not understand how such a Midwestern, urban setting could have a picturesque beach. It's hard to imagine Lake Michigan resembling any ocean view without seeing it firsthand. But once you set eyes on the dreamy blue waters from the soft sand, you'll get it. 

Complete with volleyball, biking, an ADA accessible beach walk, bathrooms, a café, and even Wi-Fi, Oak Street Beach is an oasis for Chicagoans and suburbanites alike. If you're driving down Lake Shore Drive, you'll see throngs of beachgoers having the time of their life. Under the watchful gaze of downtown, with one of the best views around from the sand, you never forget that you're in the heart of a city. 

Even out of towners are astounded by how clean and incredible the beach is. One visitor wrote on Tripadvisor: "This beach is surprisingly clean for being located in the middle of a large metropolitan area. The large city buildings make for some awesome background for your pictures. Nice hotels and restaurants surround the beach so even if the weather is not ideal you can have a nice day. Great activity for families as well as couples." 

That's part of the charm of this Chicago beach. If there is a temporary swim ban or the weather isn't warm enough, you can still enjoy a day here. I can tell you from my own personal experience, even an impending storm doesn't stop Chicagoans from having a good time at a beach. We're the Third Coast, after all, and Lake Michigan lives up to that hype. 

The popularity of Oak Street Beach is not a new phenomenon. Dating back to the 1890s, when the city was shoring up the lakefront from potential shoreline damage, Oak Street Beach was born. It quickly became a popular beach locale and is part of the reason the city expanded Ohio Street Beach — because Oak Street proved a bit too popular. Even in the 1920s, it was estimated that 55,000 beachgoers were enjoying Oak Street Beach during the steamy Chicago summers. 

Clearly, the passing of a whole century hasn't diminished Oak Street's immense popularity. Since Chicago's beaches are free, they remain a huge part of life in the city. Don't be surprised if the beachfront is chock full of people on any given weekend from Memorial Day to Labor Day. Your best bet for a more enjoyable experience with fewer crowds is to stop by on a weekday. But even then you'll see a lot of folks enjoying the blissful summertime sunshine, just as they did over a 130 years ago. And when you're done at the beach, if you're in the mood for a summer road trip, look no further than the most stunning and storied routes, some of which start in Chicago.