48 Hours in Chicago SouthlandThe Perfect Weekend in Chicago Southland starts here. From cozy brunch spots and historic breweries to boutique shopping, outdoor adventures, and unforgettable deep-dish pizza—this itinerary has everything you need for a well-rounded escape just outside Chicago. AuthorsGettingStamped
DestinationsChicagoItinerary

Day 1

La Banque Hotel
Home for this trip was La Banque Hotel, a boutique hotel built inside a former bank. Alongside the accommodations are many original architectural features and even a historic vault! It’s a distinctive blend of French-inspired luxury and history you won’t find elsewhere.
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The Bistro On Sterling
Start the weekend at The Bistro on Sterling in Flossmoor, where Chef Yvette brings creativity and heart to every dish in a historic, art-filled space. Standouts are the family-recipe chicken and New Orleans Pasta — perfectly seasoned, and served with soul, a must-visit for brunch.
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Flossmoor Station Restaurant & Brewery
Visit Flossmoor Station Brewery, located in a beautifully restored 1906 train station that still retains all of its architectural glory. It’s one of those community staples with great food, top-notch beers, and a great spot to meet. Outside, enjoy the spacious beer garden featuring a real train caboose—perfect to enjoy one of their award-winning brews!
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69 Prime Italian Steakhouse
Cap off your first day with dinner at 69 Prime, an upscale steakhouse in Homewood known for its prime cuts and craft cocktails. With an elegant atmosphere and attentive service, this was one of our favorite meals in Chicago Southland!
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Bottle & Bottega by Painting with a Twist
Spend the evening at Bottle & Bottega in Homewood, where a guided painting class is paired with wine in a relaxed studio setting where wine sipping is welcome. No experience is needed—just bring your creativity and enjoy an interactive, hands-on experience perfect for a fun date night.
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Day 2

Irons Oaks Environmental Learning Center
The high ropes challenge course is ideal for pushing your personal limits while surrounded by peaceful forest trails.
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Grady's Snack N' Dine
Start the next morning with breakfast at Grady’s, a retro-style diner known for its vibrant interior and generous portions. Vintage neon signs, vinyl booths, and a jukebox set the scene for a nostalgic and delicious start to the day.
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The Candle Vault
Create your own candle at Candle Vault in Frankfort, located in a former bank complete with probably the coolest original bank vault door I’ve ever seen. Craft your own unique candle with 140+ scents to choose from with this guided hands-on experience.
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The Jolly Giraffe
Browse Jolly Giraffe Bookstore, an independent shop offering books, games, and gifts for all ages. With its kid-friendly design complete with a life-sized giraffe statue (yes, like real giraffe-sized), secret reading room, and personalized recommendations from the shop owner, this is a must-visit for anyone with children in their lives.
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Francesca's Fortunato
Enjoy lunch at Francesca’s Fortunato, a Rome- and Tuscan-inspired Italian restaurant in downtown Frankfort. Everything from Nonna’s Meatballs to perfect pasta and everything in between, all of the flavors are on point.
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Whimsy Frankfort
you need to find your way to Whimsy Boutique for a unique and highly curated shopping experience. Known for its personalized service and exceptional collections, it’s a beautifully decorated shop with lots of fashion you won’t find elsewhere.
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Hammar's Mercantile
Hammar’s Mercantile, a boutique shop offering home décor, artisan foods, antiques, and handcrafted items. The store’s rustic aesthetic and one-of-a-kind pieces make it a must-visit for lovers of vintage style and local craftsmanship.
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Lou Malnati's Pizzeria
Wrap up the weekend at Lou Malnati’s, one of the Chicago area’s most iconic pizzerias. You can’t leave the Chicago area without trying its legendary deep-dish pizza - it’s a classic experience in a fun atmosphere that captures the taste of Chicago in every cheesy bite.
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