Top, Best & Fun Rooftop Bars in Gary

"Frequently recognized as one of Chicago’s best brunch spots, the family-owned Nana in Bridgeport has just reopened in May 2021. Boasting a delicious brunch menu made with sustainably and ethically sourced organic ingredients from local farmers, Nana offers a unique array of Mexican-American food. There are some extraordinary Latin-influenced brunch options that you’re unlikely to find anywhere else in the Windy City."

"The grilled shrimp for Nana's po' boy are season with Chile de árbol, garlic and parsley, while the oysters are soaked in buttermilk for two days, dredged in a Cajun rub and deep-fried. The sandwich is finished with a house-made gribiche flavored with whole grain mustard, roasted garlic, tarragon, caperberries and fresh lemon juice. Watch the Video: Elaborate Shrimp-Oyster Po'Boy"

"All airy and light, with exposed brick and local art, nana is a locally sourced, feel-good brunch spot in the heart of White Sox country. The family-owned restaurant works closely with area farmers to develop its organic, Latin-influenced menu full of overstuffed empanadas, po'boys, and, the stand out, baked chilaquiles topped with poblano cream and two eggs, any style."

"As bourbon drinkers, we are always ready to compare everything we taste to the best of what Kentucky has to offer. 18th Street's Rye and new 3 year Rye..."

"Though Chicago might be a major population center and port of call, it’s still hip deep in midwest agrarian culture. Homestead has a rooftop garden that reflects both the pastoral and the civilized, with drinks and food that clearly have taproots in natural flavoring and healthy living."

"Locals still tell friends to meet them at “Jimmy’s” the name of the the bar’s former owner (Jimmy Wilson died in 1999). Regardless, this tried and true dive bar has provided a meeting point for generations of college students, professors, and Hyde Park residents. Pitchers of beer are popular here as are the burgers."

"Tucked away to the left of the cupcakes is a tiny ice cream display in this cupcake shop. All their ice cream is homemade and the cookie sandwiches and cupcake shakes are the perfect combination of ice cream and your favorite baked goods."

"Restaurants Bakeries Garfield Ridge. If you grew up in the Midwest, there’s a good chance your archetype of a bakery looks a lot like this Southwest Side institution. After all, the focus at this perpetually packed spot is on hearty, comforting fare that’s descended from German, Polish and Scandinavian roots, yet over time has evolved into its own regional character."

"A Southwest Side staple, Weber’s Bakery has been pleasing Chicagoans for decades. Eaters might have to wait in line but it’s worth it for a taste of the European-inspired breads, cakes and pastries. To celebrate the holiday season, customers can choose specialty goods like gingerbread houses, Christmas cookies, fruit cakes and more."

"Like Dinkels, Webers has been around for a long time (since 1930 to be exact). And if you’ve ever eaten those tiny pre-packaged glazed donuts at the gas station, this South Side shop is for you. Specifically their chocolate-covered cake donut."