The short, but oh so sweet summers in Chicago extend just a little longer this year with some last-minute ways to soak up the last of the season. Here are a few ways to make summer endless in the Windy City.
Hit the Beach
Open long after Labor Day, the Shore Club boasts a series of fun events for guests and visitors to extend the summer fun through September. Located along North Lakeshore Drive, the beachfront destination offers everything summer fun from Rosé Fest on the Beach Sept. 15, 2–5 p.m. More in the mood for a stiff cocktail by the water? Whiskeyfest on the Beach Sept. 22, 2–5 p.m., may be more your speed. While the weather chills a little in October, so does the beach — just in time for Oktoberfest on the Beach Oct. 6, 12–4 p.m., While day drinking on the beach may be more for the older kids, it’s still a great venue to pop by and extend your summer fun.
Summer Blockbusters
Catch a summer blockbuster, Chicago-style, with an incredible view from the roof. Think, movies in the park, but with a chic city twist. During ROOF on theWit’s Movie Monday series, visitors catch a flick with the family at 8:30 p.m. at theWit hotel. Located on State Street at the famous ROOF lounge, guests 21 and older can enjoy the film with complimentary popcorn.
Open-Air Markets

Randolph Street Market © Ernitz | Dreamstime.com
Just because summer is fading doesn’t mean Chicago’s open-air market scene has to. The Randolph Street Market welcomes its 15th year this September, with open shopping dates Sept. 29–30. Expect European-style antiques, vintage finds and homemade goods at the downtown Chicago venue. It’s a high street-meets-low-street vibe and quenches the open-air shopping market thirst the summer tends to bring.
Located in Chicago’s West Loop and Fulton Market area, the district is a known gem for resident and traveling treasure hunters alike. Market dates are limited, so in-the-know travelers make a point to stop by before the seasons change.
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