Just beyond the city limits, the Chicago Southland blends big-city energy with small-town charm, scenic escapes and vibrant experiences. Whether you’re planning a family adventure, a foodie road trip or an outdoor retreat, Chicago’s south and southwest communities deliver—Where Boring Doesn’t Exist.

With hundreds of annual festivals, miles of trails, and acres of parks and waterways, the Southland is perfect for biking, kayaking, hiking and exploring. You’ll also find lively arts, local breweries, unique shops and family attractions—all just a short drive or train ride from the heart of Chicago.

Sports fans will find no shortage of action, from minor league baseball games and indoor sports complexes to golf courses and championship BMX tracks. History buffs can dig into the region’s deep roots at museums, historic downtowns and cultural landmarks that celebrate the people and stories that shaped the area.

Whether you're traveling with a group, visiting on business, or planning a weekend escape, the Chicago Southland offers welcoming hospitality and easy access to everything Chicagoland has to offer. It’s a place where communities come alive with authentic experiences, and visitors feel like locals from the moment they arrive.

Popular Attractions

• Wind Creek Chicago Southland Casino – A world-class casino experience with gaming, dining and entertainment.

• In the Game Hollywood Park – Family fun center with arcade games, go-karts and mini golf.

• Windy City ThunderBolts – Affordable, family-friendly baseball action at Ozinga Field in Crestwood.

• SeatGeek Stadium – Premier venue for soccer, concerts and major outdoor events.

• Lotton Art Glass – Handblown glass art studio showcasing vibrant, one-of-a-kind creations.

• Illinois Philharmonic Orchestra – Acclaimed orchestra delivering powerful performances in the Southland.

• Fox Pointe – Outdoor amphitheater hosting concerts, festivals and seasonal community events.

• Pullman National Historical Park – A nearby historic site celebrating industrial and labor history.

• Nathan Manilow Sculpture Park (Governors State University) – A large open-air museum of contemporary sculpture.

• Lake Katherine Nature Center – A serene escape with trails, wildlife, gardens, and lake activities in Palos Heights.

Chicago Southland Outdoor Recreation

• Forest Preserves of Cook County/Forest Preserve District of Will County – Thousands of acres of trails, woodlands, and picnic areas for hiking, birdwatching, and family outings.

• Sand Ridge Nature Center – Environmental education and natural trails with abundant wildlife.

•   Cal-Sag Trail – A scenic, multi-use path perfect for biking, running, and exploring.

• The Center – Nature trails, farm animals, and peaceful retreats in the woods.

• Irons Oaks Environmental Learning Center – Outdoor adventure campus with trails, team-building and high ropes courses.

• Lake Katherine – A serene nature center with walking paths, gardens and kayaking.

• Monee Reservoir – A quiet getaway for fishing, kayaking, hiking and wildlife viewing.

Wineries, Breweries, and Distilleries

• Blue Island Beer Company (Blue Island) – Small-batch beers and community events.

• Crozehead Cooperage and Whiskey Experience (Monee) - Experience handcrafted barrels and whiskey tastings at this veteran-owned cooperage.

• Evil Horse Alehouse & Spirits (Crete) – Popular local taproom and rotating craft brews.

• Flossmoor Station Restaurant & Brewery (Flossmoor) – A brewpub housed in a historic train station with award-winning beers.

• Homewood Brewing Bo. (Homewood) – is a vibrant, community-rooted brewpub in celebrating the legacy of Juice WRLD.

• Thornton Distilling Co. (Thornton) – Historic distillery crafting spirits where Illinois’ oldest brewery once stood.

• Vintrendi Wine Company - Boutique winery blending bold flavors with modern, urban wine culture. Olympia Fields.

• Wild Blossom Meadery & Winery (Chicago) - Sip eco-friendly meads made from local honey at Wild Blossom.

Other Interesting Things to Do

• Antique  & Specialty Shopping in Flossmoor, Frankfort, Homewood and Orland Park – Explore unique vintage finds and unique gifts across charming walkable downtowns.

• Attend a Seasonal Festival – From Frankfort Fall Fest to Southland's Irish Fest and Brew & Vine events, there are over 800 to choose from.

• Play a Round of Golf – With 29 public courses, the Southland is a golfer’s paradise.

• Toss a Disc – With 11 scenic courses, the Southland is a disc golfer’s playground.

Arts & Culture

• Flossmoor Sculpture Gardens – Outdoor art space showcasing inspiring sculptures and natural beauty.

• Lotton Art Glass Gallery & Studios – Vibrant gallery featuring unique handblown glass creations and workshops.

• Richard Haas Murals – Stunning architectural murals bringing local history and buildings to life.

• The Drama Group – Community theater offering diverse productions and creative performances.

• The Lyric Theater – Historic venue presenting classic and contemporary stage performances.

• Peotone Windmill – Iconic landmark celebrating local heritage and Dutch-style architecture.

• Stellwagen Farm – Family-friendly farm with seasonal events, animals and fresh produce.