Memories for Millennials

Make the memories of a lifetime with your entire group in the Chicago Southland! Experience local cuisine, explore unique sights and sounds and enjoy regional arts and culture. This millennial-approved vacay is sure to be an unforgettable adventure!

Day 1

Enjoy fresh, Southern-style cooking right here in the Midwest! Start your Chicago Southland road trip off with a hearty meal at Cracker Barrel in Tinley Park. Cracker Barrel serves an abundance of delicious foods, like their all-day breakfast or rotating daily specials. Southern-fried steak, cheeseburgers, seafood and more are also available. Don’t forget to check out the old country gift shop before you leave!

After filling up, head to Frankfort for some shopping in the downtown historic district. Browse the one-of-a-kind boutiques and shops in this beautiful, quaint neighborhood. Pick out a sweet treat like a vintage-style candy apple from Short & Sweet (26 Ash Street) or nostalgic candy from Raffy’s Candy Store (21 South White Street). Several gift shops can also be found in downtown Frankfort, ensuring you will find souvenirs for everyone on your list. Please allow 2-3 hours to fully enjoy all that downtown Frankfort has to offer.

Next, go to Lake Katherine Nature Center & Botanic Gardens in Palos Heights for an amazing outdoor adventure! Venture out onto the beautiful lake after renting a kayak or canoe. If you prefer to stay on dry land, take a stroll around the grounds, where you will find beautiful grasses, flowers and shrubs. There are several trails around the lake and along the Cal-Sag Channel perfect for an afternoon hike, and don’t miss the gorgeous man-made waterfall!

You’re sure to have worked up an appetite after exploring, so head over to Sheep’s Food District in Orland Park. Sheep’s Food District is a unique dining experience with plenty of options to choose from. Described as a chef-driven food hall, Sheep’s Food District currently has three local vendors serving everything from pizza to tacos to Texas-style barbecue. Plus, enjoy a drink from The District Bar, which features an ever-changing, expansive menu.

End your first evening in the Chicago Southland at Dave & Buster’s in Orland Park. This 24,000 square foot facility is sure to thrill! There are plenty of arcade games to choose from, such as classics like Pop-A-Shot, Pac-Man and Skee-Ball. A variety of the newest games are available too, including virtual reality. Step outside the arcade for a game of pool in the billiards area or watch your favorite sports at the bar. How ever you choose to spend your night, you’re sure to enjoy yourself at Dave & Buster’s!

Day 2

Begin your second day in the Chicago Southland with a delicious breakfast from Stacked Pancake House in Crestwood. These pancakes are a must-try while visiting the Chicago Southland! Classic buttermilk, red velvet, Oreo, strawberry cheesecake and lemon blueberry pancakes are just some of the mouth-watering breakfast options from Stacked. Skillets, omelets, crepes, French toast, waffles and more are also available. Fresh juice and coffee are available for a pick-me-up to help kick-start your day.

After breakfast, get the adrenaline pumping at Odyssey Fun World in Tinley Park! Odyssey Fun World will keep you and your group entertained for hours! An arcade, a zip-line, bumper boats, batting cages, miniature golf, laser tag, bumper cars, a Ferris wheel, an indoor roller coaster and go-karts are just some of the available attractions your squad can enjoy!

Settle down for some lunch and enjoy a Chicagoland classic: pizza! Stop by Ed & Joe’s Restaurant & Pizzeria in downtown Tinley Park. In business now for over 60 years, Ed & Joe’s is the perfect spot to meet and eat! Sample some deep dish or thin crust ‘za, or other favorites like pasta and sandwiches.

Next, get ready for some brewery hopping in Tinley Park! First up, visit Hailstorm Brewing Co., which features a full taproom with 16 rotating house beers on tap and seasonal craft beers. Try Hailstorm’s award-winning flagship beer, Prairie Madness IPA, or sample different brews with a $5 flight.

Afterwards, head over to Soundgrowler Brewing Co., a “doom metal” brewery with a full taproom. Soundgrowler has a wide variety of beers on tap, including their Mexican lager, Tortilla Hands, and their Belgian style saison, Pitchfork. Hungry? This award-winning brewery also features a full kitchen that serves Mexican street food.

Finally, there’s plenty more to SeatGeek Stadium in Bridgeview than just professional soccer. With a capacity of 28,000, concerts promoters and fans alike love the venue. While festivals regularly book the venue, other acts that have jammed here include Dave Matthews Band, Jimmy Buffett, Kelly Clarkson and Kenny Chesney.

Day 3

Start your final day in the Chicago Southland off right with breakfast and coffee from redbird café in Homewood. A globally inspired, farm-to-table café, redbird offers clean food prepared with local, organic produce. There are plenty of vegan and vegetarian options available at redbird café. Breakfast tacos, okonomiyaki (Japanese-inspired egg pancakes), breakfast burritos and more await you!

Sip your coffee as you stroll around downtown Homewood and search for the Richard Haas murals. Homewood is home to the world’s largest collection of Richard Haas murals. These illusion-style murals can be found throughout the town; can you find them all? Here’s a map to help you get started.

Feast your eyes on even more incredible art at the Nathan Manilow Sculpture Park in University Park. This incredible sculpture park sits on the campus of Governors State University and features 30 master works of large-scale sculpture, spread across 100 acres of prairie landscape. Open to the public 365 days of the year, the Nathan Manilow Sculpture Park is free of charge. Plus, it makes for an amazing photo op! Share all of your pics on social media and be sure to use #ChicagoSouthland!

After taking in some uniquely Chicago Southland art, grab some lunch at Bar Louie in Matteson. Featuring an impressive menu, including limited-time options, Bar Louie is the perfect place to unwind and enjoy a good meal. Share an appetizer, like the flash-fried calamari or loaded tots. Craft burgers, scratch-built sandwiches, salads and more entrees are available. Don’t forget dessert!

When you’re finished with lunch, pay a visit to Vintrendi Wine Company in Park Forest for a wine tasting. The wine connoisseurs at Vintrendi create wines with age-old wine making techniques that satisfy modern day taste buds. Tastings include four 3 oz. pours of your choice. Click here to see Vintrendi’s full menu.

Next, visit Gamma VR in Lansing and be transported to a different world! Experience the future of entertainment through the wonders of virtual reality. Become a boxer, an elven assassin, a hacker and so much more at Gamma VR!

Time for dinner! Grab some grub at Beggars Pizza in Lansing. Beggars is known for laying it on thick when it comes to pizza ingredients! Don’t miss your chance to sample another Chicagoland favorite: Italian beef sandwiches! Try the classic or “The Godfather,” which includes Italian beef, sweet peppers, mozzarella and meat sauce on garlic bread.

Wrap up your Chicago Southland adventure on a sweet note! Stop by Gayety’s Chocolates & Ice Cream Co. in Lansing. For the last century, Gayety’s has been handcrafting delicious, high-quality treats like chocolates and homemade ice cream. Enjoy satisfying your sweet tooth at this famous spot!  

Map out your complete adventure! Click here to visit our free, interactive app, where you can see this road trip mapped out, plus create your own custom itineraries, check out upcoming events and read more about local attractions or amenities, and so much more! Don't forget to book your hotel! Click here to visit our Chicago Southland accommodations page.