Grab your best girlfriends and head to the Chicago Southland for an unforgettable getaway! Get ready for a trip filled with shopping, wine, art, delectable dining and so much more. We can’t wait to welcome you and your girls to the Chicago Southland!
Start your girls’ getaway with a spot of tea! Pekoe & Bean in Tinley Park is a charming tearoom and coffee bar. You and your girls can warm up with a hot cup of tea or coffee while enjoying light fare such as scones, finger sandwiches and more.
After tea, get ready to shop until you drop! Head over to downtown Frankfort and visit the historic district. This charming area is chock-full of boutiques, gift shops, specialty stores and more. You will love walking through this quaint neighborhood while searching for your next treasure.
You’re sure to have worked up an appetite after shopping around historic downtown Frankfort! Head to lunch at Stoney Point Grill in Mokena. Stoney Point Grill is an upscale restaurant that serves American cuisine. Enjoy steak, seafood, signature sandwiches, gourmet burgers and more. Eat by the fireplace or at the beautiful granite bar.
After filling up on lunch, it’s time to enjoy the second half of your shopping excursion! Visit Orland Square, the expansive mall in Orland Park. Shop at flagship stores like Von Maur or Macy’s and don’t forget to visit Apple, Alex & Ani, MAC, Pandora, Williams-Sonoma, Sephora or any of the other 150 stores and restaurants in the mall! Be sure to give your group plenty of time to explore Orland Square.
Wrap up Day 1 at Cooper’s Hawk Winery & Restaurant in Orland Park. This award-winning winery is the perfect way to spend your first evening in the Chicago Southland. Experience their eclectic menu designed to pair perfectly with their handcrafted wines. Each dish is made fresh by Cooper’s Hawk chefs from the highest quality ingredients. Plus, you can even schedule a wine tasting. Don’t forget to peruse the gift shop as well!
Fill up on brunch before heading out for your second day of adventure! Stacked Pancake House in Crestwood serves incredible breakfast options like buttermilk pancakes, red velvet French toast, chicken and waffles, Greek omelets and more. Enjoy a glass of fresh squeezed orange juice or a café latte for an instant pick-me-up! Stacked also has plenty of lunch options to enjoy like soups, salads and sandwiches.
After brunch, head to Lotton Art Glass Gallery & Studios in Crete for a unique visit to one of the Chicago Southland’s hidden gems. Your girl group can experience the thrill of watching magnificent works of art being created out of hot glass, right before your eyes! Meet the world-famous Lotton family and tour the gallery, full of beautiful glass creations. Simply admire the one-of-a-kind works of art or purchase one to bring back home!
Your next stop is Vintrendi Wine Company in Park Forest. Vintrendi is a boutique winery that creates wines without rules. All of Vintrendi’s wines are created with established winery partners, from start to finish. Sample the wines for yourself at a wine tasting in Vintrendi’s café or tasting room. Bottles are also available for purchase!
Homestyle Italian cooking awaits you at Balagio Ristorante in Homewood. Enjoy a wonderful dinner of bruschetta, gnocchi, chicken parmesan and other classic Italian dishes. Pair your dish with a cocktail or glass of wine from Balagio’s expansive drink menu. Buon appetito!
The day isn’t over yet! Stop by Culture in Homewood for some late-night celebrating! Culture frequently hosts live entertainment for their guests to enjoy. Try a “Culture Cocktail” or enjoy a glass of wine, and don’t forget to dance the night away! Please note that reservations are highly recommended for Culture’s live performances.
Begin your last day in the Chicago Southland with a stroll around the beautiful Art Garden of Palos Heights. This art garden features outdoor sculptures and eco-friendly gardens. Plus, additional sculptures and murals can be found throughout Palos Heights. Don’t forget your map! A self-guided tour map can be found here.
Ready for lunch? Head to Chicago Gaelic Park in Oak Forest! Their on-site restaurant and pub, The Carraig, serves delectable Irish fare, like the Celtic steak sandwich, the classic Reuben or Irish sausage and chips. Celebrate the South Side Irish with this must-visit location!
Continue your artful morning at Lake Katherine Nature Center & Botanic Gardens. In addition to the sculptures that can be found at Lake Katherine, you and your girls can also enjoy hiking, kayaking, cycling, nature watching and more throughout the 85-acre natural refuge. Lake Katherine also features a beautiful man-made waterfall that is the perfect spot for relaxing.
Take a walk around McCord Gallery & Cultural Center in Palos Park. McCord Gallery is a not-for-profit learning center that showcases the incredible artwork of both local and regional artists. Nearly 120 music students and 100 art students attend sessions at the gallery. Passionate volunteers work six days a week at McCord Gallery; you won’t want to miss this wonderful location.
Next, it’s time for dinner at Harvest Room in Palos Heights. Enjoy the open, airy dining room and sample farm-to-table meals. Harvest Room features gluten-free and vegan options as well! Take advantage of the full-service bar that serves handcrafted cocktails and fine wines.
Save room for wine and visit Wild Blossom Meadery & Winery in the Beverly neighborhood of Chicago. Wild Blossom was the first winery in Chicago! As a meadery, Wild Blossom raises their own bees and collects their own honey. Sample the expertly made mead or wine in Wild Blossom’s tasting room. Plus, take a tour of the facility and learn about Wild Blossom’s beehives and mead-making process. Bottles are also available for purchase.
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.