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.
Read This Next
#WhereverFamily
Insta FeedHotels
Sep 1, 2026Hyatt Regency Maui Resort and Spa to Welcome Return of Elf on the Shelf This Holiday Season
The magic of Christmas quickly approaches as summer comes to a close, and families can experience the holiday season in a unique way this year.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Destinations / North America
Sep 1, 2026Family-Friendly Ways to Welcome Fall in the Finger Lakes
Some of us are still trying to stretch out the dog days of summer, but there is no denying fall will be here soon. Whether ready for it or not, it’s time to look for ways to welcome the season that will be fun for the family. Luckily, New York’s Finger Lakes region has plenty of ways to do just that.
Hotels
Sep 1, 2026This London Hotel Launches Little Londoners Family Package
Balance a city break in London with kid-friendly experiences at Sea Containers London, an upscale, riverside hotel. The property recently debuted the Little Londoners package, a thoughtfully designed offering that makes exploring London easier (and more fun) for both kids and parents.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Destinations / North America
Aug 31, 2026Dude Ranch Experience Coming to Historic Arizona Golf Resort
Later this fall, family travelers are invited to experience one of Southern Arizona’s hidden gems in a true dude ranch setting. Otero Ranch at Tubac Golf Resort & Spa opens for the season Nov. 15, presenting an experience by True Ranch Collection that will feature exclusive dude ranch adventures, such as horseback riding and hiking along the Santa Cruz River valley, playing a round of golf at the 27-hole championship course, trying 3-D archery, exploring the town of Tubac, touring historic Tumacacori Mission, and relaxing at the resort’s spa or pool.
ShareThis