Chicago's Charming Suburb Is A Lively Midwest Getaway With Pristine Parks, Diverse Dining, And A Local Winery

The train pulls into 143rd Street Station one Thursday afternoon, and you step off the platform feeling like you just discovered the city's most guarded secret. There's a moment every Chicago visitor experiences when they realize the most enchanting discoveries happen in places nobody told them to look. Maybe it's stumbling across a wooden alley in Gold Coast — one of Chicago's best neighborhoods for high-end shopping — or learning the unspoken rules everyone just expects you to follow. Sometimes it's the spontaneous decision to take the road less traveled and head south instead of north, trading crowded sidewalks for the rolling prairie of Orland Park.

The Metra Southwest Service deposits commuters into this suburb multiple times daily, connecting from Chicago's Union Station in under an hour. You venture forth expecting suburban sprawl and chain restaurants, but instead you find a community that has assembled its own version of urban sophistication, complete with a local winery collecting awards (hundreds of them, from regional to international), festivals that rival anything downtown, and a green stretch of hundreds of acres where rare birds nest. It's close enough to both airports — 25 minutes from Midway Airport and 45 minutes from O'Hare — that you could theoretically catch a morning flight and still make it back for dinner at one of the Italian or Japanese restaurants that dot the local dining scene. Chicago Magazine took note when it named Orlando Park one of the metro area's best places to live, though locals could have saved them the research.

This is Chicago, after all, so the dining expectations run high from the start. Italian trattorias sit alongside Thai kitchens, Mexican joints neighbor classic American fare, all of it woven into Orland Park's dining scene. The suburb celebrates that mix with festivals throughout the year, from summer events that showcase restaurant specialties to autumn gatherings where craft breweries and local vendors set up shop in the parks.

Blissful Banana Cafe is as good a place as any to start. A local favorite, this mom-and-pop shop opened in 2012 and quickly overtook the local food scene. The menu leans into healthier fare such as nitrate-free meats, locally grown organic produce, fresh-baked scones, and gourmet coffee with seasonal twists like bourbon crème cold brew topped with cinnamon. One Tripadvisor reviewer summed up the universal frustration: "If I had to make a complaint, it would be that they are not open past 3pm." Indeed, the early closing time does require some planning, but it has become part of the charm.

After brunch, the logical next stop involves wine — specifically, Cooper's Hawk Winery & Restaurant, where the afternoon stretches into evening without scheduling conflicts. The winery sits in an upscale-casual space that feels both sophisticated and approachable — think Napa-style tasting room meets neighborhood gathering spot. Its wine program has collected over 500 awards, including a 99-point rating for its Lux Pinot Noir. Guided tastings include eight different selections, and Master Sommelier Emily Wines — one of only 149 in the Americas — oversees a program that takes wine education as seriously as wine enjoyment. After sampling your way through the latest releases, you can browse the marketplace for decanters and accessories, or settle into the restaurant side for dinner paired with monthly wine selections.

Orland Park counts over 60 parks within its boundaries, which sounds impressive until you realize one of them spans more than 750 acres and exists primarily as a love letter to Illinois before European settlement. In 2002 someone looked at this former farmland and formed the audacious goal of bringing back an ecosystem that had vanished from Illinois so completely that less than a fraction of 1% of the state's original prairie remained.

The statistics tell one story: Illinois once held millions of acres of native prairie, and today, merely 0.001% remains. Orland Grassland tells another story entirely. Walking the trail system that winds through native grasses and wildflowers, you might spot a Henslow's sparrow or catch sandhill cranes on a migration stop. Coyotes stalk across the land, while harriers and Cooper's hawks circle overhead. The restoration team disabled miles of drainage tiles left over from the farming era, allowing the land's natural water systems to return. Streams flow again, ponds reflect the sky, and wetlands provide habitat for everything from sora rails to eastern kingbirds.

Bird enthusiasts make pilgrimages here for species they can't find anywhere else in the region. The annual volunteer bird count regularly logs over 100 species, including warblers, dunlins, and phalaropes that treat the grassland as a crucial rest stop. But you don't need binoculars to appreciate what's happening here. Purple prairie clover and grass-leaved goldenrod add splashes of color to the landscape, while towering compass plants and prairie dock create natural landmarks across the rolling terrain. With the exception of being surrounded by suburbs instead of endless wilderness, standing in the middle of all 750 acres of restored prairie feels like stepping into an Illinois that existed centuries ago.