Bon Voyage, Baby Boomers!

People of all ages love to travel—including Baby Boomers! There are 76 million Baby Boomers in the United States alone, making them one of the largest generations in American history. 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!

Day 1

Begin your visit to the Chicago Southland with a shopping spree! Three Sisters Antique Mall in Blue Island was voted Chicago Southland’s Best for Antiques for 20 years straight. With over 60 dealers filling two huge floors of shopping space, Three Sisters is a must-see while visiting the Chicago Southland. Visitors will love browsing the shelves and searching for unique finds like clothing, jewelry, collectibles and more.

Next, take a trip back in time when you head to the 1950s Park Forest House Museum in Park Forest! This unique museum interprets an original home built between 1947 and 1949 by American Community Builders. The museum is furnished with pieces from the 1950s and 1960s, creating a nostalgic trip down Memory Lane for anyone who lived through that era. Visitors are encouraged to explore every drawer, cupboard and closet to discover even more period treasures! Baby Boomers visiting the Chicago Southland won’t want to miss this awesome blast from the past.

After enjoying the museum, head to Flossmoor Station Restaurant & Brewery in Flossmoor for lunch. Located in a historic former train station, Flossmoor Station is the area’s oldest brewery. Relax with a pint of their flagship beer, Rail Hopper (IPA), while enjoying a delicious lunch and watching the Metra trains go by.

Take a post-lunch stroll through downtown Homewood and look for the Richard Haas murals scattered throughout town. Homewood boasts the largest collection of these illusion murals. Can you find them all? Click here for a map to help guide you!

After your mural scavenger hunt, get ready for more Chicago Southland shopping! Your next stop is Lotton Art Glass Gallery & Studios in Crete. For over 50 years, the talented artists at Lotton Art Glass have been creating beautiful, one-of-a-kind works of art, fashioned out of hot glass. Visitors can even see the artists at work and enjoy a live glass-blowing demonstration. Don’t forget to tour the studio, where you can purchase an exclusive Lotton Art Glass creation, like vases, bowls, paperweights and more.

Wrap up your exciting first day in the Chicago Southland with dinner from The Princess Cafe in Beecher. Since 1977, The Princess Cafe has been serving the finest steaks, seafood and chops. End the evening by enjoying a cocktail with your meal, in The Princess Cafe’s relaxing country atmosphere.

Day 2

Kick off Day 2 by enjoying some of the Chicago Southland’s beautiful forestry at Monee Reservoir in Monee. Visit the 46-acre lake, perfect for fishing. If you’re feeling adventurous, rent a kayak or canoe! Monee Reservoir is also a great spot for hiking, running or picnicking in the summertime and cross-country skiing or snowshoeing in the wintertime, making this a perfect location for year-round Baby Boomer road trips!

Continue your adventure by heading to Nathan Manilow Sculpture Park in University Park. This is a must-see while visiting the Chicago Southland! The Nathan Manilow Sculpture Park is a collection of 30 larger-than-life sculptures, situated within 100 acres of beautiful prairie landscape. This park is open to the public 365 days a year and is free of charge. You won’t want to miss this incredible stop!

After visiting the sculpture park, head to Bar Louie in Matteson for lunch. Bar Louie offers an expansive menu, featuring everything from burgers and sandwiches to seafood and salads. Don’t forget dessert!

Spend your afternoon visiting the Frankfort Historic District. This quaint downtown area features charming stores and eclectic boutiques. Take a stroll through town and shop for Chicago Southland souvenirs for everyone on your list! There are gift shops, candy shops, clothing stores and even a pet store. Grab a cup of coffee at Grounded Coffee Bar (located at 19 Ash Street) or browse the trinkets at Glory Bee Gift Shop (located at 122 West Kansas Street). Allow 2-3 hours to fully enjoy everything that the Frankfort Historic District has to offer.

Next, get dressed up for a night out on the town right in Frankfort, where you’ll find Francesca's Fortunato. Make sure you bring your appetite! The menu features the zesty earthy cuisine of Rome and the surrounding areas of Tuscany, Umbria and Lazio. Ciao!

After dinner, head to one of the many live music venues in the Chicago Southland for some evening entertainment. Fox Pointe in Lansing or the Country Club Hills Theater in Country Club Hills are just a couple of the venues to choose from! There are also plenty of performing arts centers in the Chicago Southland, like Freedom Hall in Park Forest or the Illinois Philharmonic Orchestra, which performs all throughout the Chicago Southland. Please check for performances ahead of time! For more live music venues in the Chicago Southland, go here.

Day 3

Wind down your Chicago Southland visit 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. 

After enjoying a game of golf, end your Chicago Southland adventure with a delicious dinner from Jack Gibbons Gardens in Oak Forest. Jack Gibbons Gardens opened in 1922, and since then, they have been providing diners with great food, great atmosphere and great service. This restaurant was recognized as one of the Chicago area’s great steak houses! Jack Gibbons Gardens also serves fresh seafood, pork chops and chicken, plus a wide array of delectable desserts. This award-winning establishment is the perfect way to end an amazing visit to the Chicago Southland!

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.