Southland's Entertainment & NightlifeWhether you're looking for things to do in the Chicago area this week, this weekend, or next month, the Southland has you covered! From unique places to shop, top spots for entertainment, the best bars and breweries, and even a casino, save these ideas for your next trip to the Chicago Southland.AuthorsSteller
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Best Places for Entertainment

Wind Creek Chicago Southland
There's more than 70,000 square-feet of gaming space at this hotel and casino! With 56 table games and over 1,400 slot machines, a new luxury spa (coming soon), plus six unique places to dine, including an oyster bar, Wind Creek Chicago Southland, may be the perfect place for your next weekend getaway or girls' night out.
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Fox Pointe
Fox Pointe, in Lansing, is one of the best spots in the Chicago Southland for live music and events in the summer. Not only does the outdoor amphitheater have lush green grass to spread out on and great acoustics, but most of the concerts and events are FREE! 🎤
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SeatGeek Stadium
Home of the Chicago Stars FC! Catch a soccer or rugby game here throughout the year, or a concert in the summer. And check out the biggest independent hip-hop music festival, Summer Smash, in June!
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Illinois Philharmonic Orchestra
Enjoy classical music masterpieces by Mozart and Schubert, and tributes to modern composers like John Williams by the Illinois Philharmonic Orchestra—the Chicago Southland's largest performing arts organization!
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Center For Performing Arts
A fun place to see a live performance, enjoy everything from dance to jazz on the stage at the Center for Performing Arts at Governors State University.
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The Lyric Theater Blue Island
This historic theater was completely renovated inside, making it a cool, unique space for a movie night unlike any other! Slip into a booth with friends or grab a bar stool as you sip your drink and watch a flick. 🍿 Or stop in for a variety of live shows and musical performances throughout the year.
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Best Day Trip Idea

Frankfort Area Historical Society
Looking for the perfect day trip? How about a girls' weekend getaway? The historic small town of Frankfort in the south suburbs of Chicago features charming streets lined with cute shops and cafés, and is surrounded by beautiful historic homes. Don't forget to bring your bike or your running shoes! The paved 21-mile Old Plank Road Trail Bike Path built on an abandoned railroad line winds through neighboring towns, oak woods, and across open prairie landscapes.
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Best Places to Shop

Orland Square
Shop till you drop in one of the largest malls in the Chicago Southland: Orland Square Mall. Nestled in Orland Park, this is a go-to shopping and dining destination! Find all your favorite stores, including Lululemon, Coach, and Apple. When you're done shopping, enjoy a meal at popular restaurants like the Cheesecake Factory and Texas de Brazil. 🛍️
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Loulou Belle
Love to shop small? Check out LouLou Belle in Homewood. The independent store works with talented artists and artisans to stock its shelves with the cutest hand-crafted gifts and one-of-a-kind items, including jewelry, botanical prints, and pottery.
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Blue Pearl Candles
You can smell their work down the street! Shop their hand-poured, scented candles, cute home accessories, and more, or experience making your own candle at Blue Pearl. Gather some friends for the Candle Bar experience! Pick your favorite scents and make a custom candle as you enjoy some light snacks. Makes a fun girls' night activity! 🥂
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Lotton Art Glass Gallery & Studios
Stop in here to shop the one-of-a-kind hand-blown glass pieces at this family-owned studio and gallery. You can watch the artists make everything from vases to chandeliers here Monday through Friday.
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Best Places to Eat & Drink

Carraig Irish Pub
Carraig is an authentic Irish pub that was literally built in Ireland before being disassembled and shipped to Chicago's south suburb of Oak Forest where it was reassembled in Gaelic Park. Not surprisingly, this is a great place to grab a Guinness! Stop in on Friday and Saturday evenings for live music. Sláinte!
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Dunning's Gourmet Market & Deli
Looking for something fresh and homemade? Dunning's makes all of their soups, salads, and sandwiches in-house. Get the chicken salad—it's legendary. (Have dietary restrictions? They can handle them all, from dairy to gluten allergies.)
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HMD Bar and Grill
HMD, serving upscale-casual American cuisine, won OpenTable's Diners' Choice Award in 2024! In the summer, sit outside on the rooftop while you enjoy your meal and a glass of wine. 🥂
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Gayety's Chocolates & Ice Cream
If you're craving chocolate, make a stop at Gayety's! Established in 1920, people rave about their hand-dipped chocolates (especially the chocolate-covered strawberries). They also serve homemade candies and ice cream.
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Aurelio's Pizza of Homewood
When in Homewood, stopping in at this classic pizza joint for their stuffed-crust pizza is a must! Aurelio's Pizza of Homewood has been here since 1959 and is beloved by locals. 🍕
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Homewood Brewing Company
The owners specifically built HBC for the community to gather, making it a great spot to join friends for one of their seasonally brewed craft beers or their New Orleans-inspired dishes like Boudin Balls and Fried Shrimp Po Boy.
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Copper Still Martini Lounge & Speakeasy
Looking for an elegant night out? This lounge has mastered the martini—there are more than 17 to choose from between classics and their signature martinis, plus a menu of hand-crafted cocktails. They also have live music (or karaoke) most Mondays, Thursdays, and Fridays! Tip: Want to learn to make the perfect martini? You can book a class here! 🍸
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Where to Stay

Hampton Inn & Suites Bridgeview Chicago
Close to SeatGeek Stadium and the Chicago Midway Airport, the Hampton Inn & Suites Bridgeview Chicago is a super convenient place to stay in the Chicago Southland area. You'll also love the daily free hot breakfast. ☕ Only 25 minutes from downtown!
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