Best & Cool Bars in Highland

"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 team behind Nana strives for perfection by maintaining a sustainable, local and organic menu. What they serve is high-quality and delicious food. While not a completely vegetarian restaurant, the avocado fries and tofu scramble have us commending the commitment to perfection."

"Nana in Bridgeport draws diners from all over the city and is frequently listed as one of the city’s best brunch options."

"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."

"Creative Brazilian-style cakes and treats are baked at Fabiana’s Bakery, a cute space on 53rd Street in Hyde Park. Chocolate cakes and banana cream pies are highlights. Fabiana Carter also provides booze-infused desserts down the street at Bibliophile, the gastropub/cafe she and her husband run down the street."

"I mentioned Butterdough in my post about places to eat in Chicago, but I’m listing it again because their coffee is excellent. One of their most popular options is the Cafe con Leche with their homemade cafe de olla syrup. I recommend getting it with regular milk, not their oat milk because the oat didn’t work with this drink at all."

"There are only a few flavors of donuts to choose from at Butterdough in McKinley Park. But that’s fine, the horchata is what you want. The lightly-spiced glaze is poured on the donut right in front of you and pools in the container in a satisfying (and useful for extra dipping) way."

"The Smart Museum is small, free, an easy and engaging place to museums in Chicago. It’s easily accessible by public transit and there is a parking garage nearby. Exhibitions, which rotate, are really tremendous, tending towards the avant-garde but including the historical and always celebrating the vast diversity of the art world."

"Founded in 1974, the Smart Museum of Art is part of the University of Chicago and is home to acclaimed special exhibitions and a permanent collection that spans five thousand years of artistic creation."

"For more than three decades, this Chatham beacon has earned its place in the community. A popular stop for the Aretha Franklin, Josephine’s Southern Cooking is known for soul food staples like gumbo, fried catfish, and pork chop. But Franklin isn’t the restaurant’s most esteemed celebrity."

"Huck Finn Restaurant serves up hearty American meals all day, but regulars swear by their donuts.|© Salim Virji / Flickr. Huck Finn Restaurant serves up hearty home cooking all day long in three Chicagoland locations. While best known—or perhaps most appreciated—for its donuts, the diner has excellent breakfast, lunch, and dinner options, too."

"This diner mini-chain has three locations on the South Side that provide patrons with a satisfyingly sweet finish to every meal. Chow on golden brown pancakes, club sandwiches, and burgers but make sure to save some room for a donut delight. The signature treat features one of Huck’s donuts topped with choice of ice cream and whipped cream."