Oak Street Beach, an oval of golden sand snuggled between vast Lake Michigan and hectic Lake Shore Drive, is the closest beach to the best shopping, dining and outdoor recreation the Windy City has to offer.
But this little piece of beach heaven, which sits south of Division Street and north of Oak Street, didn't always exist – it emerged in the late 1800s as a build-up of sand after a shipping pier was built nearby.
And what a lucky coincidence for city-dwellers: By the 1920s, it was already a top spot to cool off and enjoy the summer sun.
Midwest Beach Appeal
Oak Street Beach has a lot going for it. First, there are the incredible skyline views, including those of famous buildings like the imposing Hancock Tower and the classic Drake Hotel. A steady stream of active types - some on bikes, some on skates and others walking or jogging - flows through the 18-mile-long multi-use trail bordering this beach and others along the lakefront.
As for the water, it's pretty chilly most of the time, but the temperature is tolerable in the late summer months and excellent for a quick dip or some impromptu wading.
Check out our video of a day at Oak Street Beach and get a taste of what this beach has to offer.
Stay for a Bite, Stay the Night
Believe or not, there are some affordable hotels within walking distance of the beach. Late summer rates at the Thompson Hotel are hovering around $170; rates at the Raffaello Hotel drop to $146 a night in early September, when the humidity and long summer daylight hours haven't yet let up. For the same date range, you'll only pay $130 a night at the Millennium Knickerbocker Hotel. For select dates in August and September, the Residence Inn Chicago Downtown has rooms for $189 a night.
Put dining on your Chicago to-do list – this is a major food city, after all. The Capital Grille and Volare get high marks, but Chicago residents flock to everyday favorites like Emilio's Tapas and Giordano's.
Though Chicago's summer beach season is winding down, there are still a few weeks to make it to the city before the autumn winds start blowing in. Check out our Chicago flight and hotel deals.