As you tick off Chicago’s major sights, from the Willis Tower to the Miracle Mile to Navy Pier, take time out to visit these local favorites — some of which are decidedly under-the-radar and others that are better known but still can’t miss:
Coffee, Street Food and Treats
The Old Town location of Chicago-based Intelligentsia Coffeebar is just a few blocks from Hotel Indigo Chicago Downtown, inside Plum Market. The cafe’s minimalist style, with large windows and a lofty ceiling, creates a bright, airy ambience, but of course the real attraction is the Fair Trade-sourced coffee.
When you want to experience that quintessential Chicago-style hot dog, eaten on the street, Downtown Dogs is a go-to spot for many. Its claim to fame is the Char Dog — grilled over charcoal, with the tell-tale, X-cut at the end of each hot dog, and served in a poppy seed bun.
Bobtail Ice Cream is the real deal for fans of the old-fashioned ice cream parlor and soda fountain. Open since 1950, the family-owned spot is famous for its signature Sunset ice cream — merlot with dark chocolate chips — which was created by original owner Grandpa Wilcoxon.
Pizza and Chef’s Creations
The Gage, located next to Millennium Park in a late 19th century landmark building, serves rustic American fare from Chef Christopher Gawronski. The lower level staircase offers a display of original magazine ads for Gage Brothers & Co. hatmaker, which once operated out of the building and serves as the inspiration for the restaurant’s name.
Helmed by Jimmy Bannos, Jr., winner of a James Beard Rising Star Chef award, The Purple Pig is a small plates restaurant specializing in antipasti, cured meats, pastas and grilled dishes. But locals also know it as a spot for breakfast, which is served Monday through Friday and includes such items as a piadina or Italian-style flatbread with asparagus, avocado and feta.
In a town known for its pie, Chicago Pizza & Oven Grinder Company stands out for its location, as well as its food. It’s situated underground in a build that’s across the street from the site of the infamous St. Valentine’s Day Massacre, a mob hit allegedly ordered by the legendary Al Capone, in 1929 Eating here is like taking a step back in time, and the place serves up an unusual “pot pie” version of pizza, as well as signature grinder sandwiches.
Where to Love the Nightlife
Detention Nightclub has a unique, after-school detention theme, complete with servers in school uniforms. Located around the corner from Hotel Indigo, it’s a fun — and convenient — spot for a night out with DJ and dancing.
The Galway Arms features all the elements of a classic Irish pub: craft beer, a menu heavy on comfort food and a regular rotation of sports on TV, from baseball to soccer. The pub also features live, traditional Irish music by Paddy Homan and his band every Sunday night.
If you’re looking for a late night spot, this is it: Open until 4 a.m., Underground Wonder Bar features live music every night spanning jazz, funk, reggae and rock. The venue also features a popular comedy show on Tuesday nights.