Road Trippin'

There’s nothing quite like a road trip. Whether you’re visiting from near or far, with friends or family, the Chicago Southland has the perfect road trip for you and your travel companions. Check out the incredible local restaurants and one-of-a-kind attractions, all while experiencing Chicago Southland-style hospitality. Get ready to pack your bags and hit the road…and don’t forget the music!

Girls Getaway – 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. On Day 1, shop ‘til you drop in historic downtown Frankfort. This charming area is chock-full of boutiques, gift shops, specialty stores and more. You’ll love walking through this quaint neighborhood while searching for your next treasure. Day 2 will take you to Vintrendi Wine Company in Park Forest. Vintrendi is a boutique winery that creates wines without rules. Sample the wines for yourself at a wine tasting in Vintrendi’s café or tasting room. Bottles are also available for purchase! Wrap up your Chicago Southland stay on Day 3 at the McCord Gallery & Cultural Center in Palos Park. This not-for-profit learning center showcases the incredible artwork of both local and regional artists. Stroll through the gallery and enjoy the artwork before grabbing dinner at the Harvest Room in Palos Heights. Enjoy the farm-to-table meals, with plenty of gluten-free and vegan options available. Take advantage of the full-service bar that serves handcrafted cocktails and fine wines, and say, “Cheers!” to a girls trip well spent in the Chicago Southland! Here's the full girls trip itinerary!

Bro-Cation in the Chicago Southland – Welcome to the Chicago Southland, gentlemen! Our region is home to 14 craft breweries, luscious golf courses and plenty of other dude-approved attractions. Start Day 1 by getting the adrenaline pumping at The Forge in Lemont. Climb, zip, rappel, soar, and more. There is an activity for all abilities and adrenaline levels. You decide where to start and what to do while you play. Keep the fun going on Day 2 with a hearty meal from Chuck’s Southern Comforts Cafe in Burbank. Fill up on pancakes or an omelet for breakfast (available until 11:30 AM) or wait until lunchtime to chow down on some of Chuck’s famous BBQ ribs, pulled pork, grilled chicken and more. No visit to the Chicago Southland would be complete without stopping at a golf course! On Day 3, head to Ravisloe Country Club in Homewood. Ravisloe is the only public Donald Ross course in Illinois and has been recognized by multiple local and national publications. After 18 holes of golf, settle in for a meal at Ravisloe’s on-site restaurant, Rossy’s Roost. Dine outside on the patio that overlooks this beautiful golf course and relish the best bro-cation ever! You can see the full bro-cation itinerary here!

Bon Voyage, Baby Boomers – People of all ages love to travel, and Baby Boomers are no exception! Here in the Chicago Southland, there are plenty of Baby Boomer-friendly things to see and do. Whether you’re looking for arts and culture, delicious dining or a round of golf, you’ll find it here in the Chicago Southland! Kick things off on Day 1 by taking a trip back in time to the 1950s Park Forest House Museum in Park Forest. This unique museum interprets an original home built between 1947 and 1949 and is furnished with pieces from the 1950s and 1960s, creating a nostalgic trip down Memory Lane for anyone who lived through that era. Baby Boomers won’t want to miss this awesome blast from the past! Work up an appetite because Day 2 will take travelers to Jack Gibbons Gardens in Oak Forest. Established in 1922, Jack Gibbons Gardens is a historical speakwasy, classic American steakhouse serving high-quality award-winning steaks, chops and seafood. Wind down your Chicago Southland visit on Day 3 with a relaxing game of golf at Silver Lake Country Club in Orland Park. This beautiful 45-hole public golf course has an attractive clubhouse with a well-stocked pro shop, locker facilities, coffee shop and banquet rooms. Click here to see the full baby boomer itinerary!

Memories for Millennials – Make the memories of a lifetime with your entire millennial squad 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 a memorable adventure! Start things off on Day 1 at Lake Katherine Nature Center in Palos Heights. Venture out onto the beautiful lake after renting a kayak or canoe, or 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. Don’t miss the gorgeous man-made waterfall! Day 2 will have you stopping 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. You’re sure to satisfy your sweet tooth at this famous spot, just one of the places that makes the Chicago Southland amazing! Check out the full itinerary here!

Go to VisitChicagoSouthland.com/RoadTrips for complete road trip itineraries and even more itinerary ideas. We can’t wait to welcome you to the Chicago Southland!