The Midwest melting pot of Chicago is more than just one big city — it’s 77 different neighborhoods smashed together on Lake Michigan’s shores. It’s better to look at this in terms of regions. Here’s a quick guide to help you plan your trip.
Office buildings, landmarks, and touristy spots make up Chicago’s skyline and repopulate an area once destroyed by a massive fire. Start your day at Skydeck or 360 Chicago, the two best views in the city with insane opportunities to suspend yourself high over the streets. Head into River North for quinoa cakes and poached eggs at Beatrix, or donuts at Bohemian House. Hit the Gold Coast after to see grand mansions in one of the oldest parts of the city. Just south from there, stop at Navy Pier in Streeterville — if it’s summer, you may catch the weekly fireworks. Have lunch at Artist’s Café across from Millennium Park in the Loop; explore Cloudgate and Maggie Daley Park on your way into the South Loop for a trip to Northerly Island, one of the remaining relics from the Chicago’s World’s Fair. Finish up with dinner at Joy Yee Noodles in Chinatown.
Bro heaven, home of the Cubs, and some of the most visited neighborhoods in Chicago. If you move in from the burbs, you’re probably moving to the North Side. Start with the mostly German Lincoln Square — you can go gourmet grocery shopping at Gene’s Sausage Shop, buy some weird but cool stuff at Enjoy and Merz Apothecary, and then pop in to Brauhaus for culturally authentic lunch. Stop over in Wrigleyville to check out the historic ballpark, then visit the Lincoln Park Zoo and spend the rest of the afternoon shopping in Boystown (don’t miss Beatnix) and Lakeview (check out Bookman’s Corner for an overwhelming selection). End your night with dinner, drinks, and improv at Second City in Old Town.
Hipsters who have grown into upper-middle-class corporate hipsters populate the West Side, which has a distinctly more artsy vibe than other areas in the city. Start in the West Loop, the most gentrified neighborhood, for chilaquiles at Au Cheval or a Bloody Mary at The Publican. Tour the West Hubbard Street murals on the way north to West Town, then check out Chicago architectural relics at Urban Remains. Stop for a beer at Happy Village’s beer garden in Ukrainian Village before going to lunch in the Puerto Rican epicenter of Humboldt Park. Café Colao specializes in authentic sandwiches. Next head to Pilsen, a predominantly Mexican neighborhood and arguably the most creative spot in Chicago with tons of indie spots, like Café Jumping Bean with local artwork on display. For dinner, go to County BBQ in Little Italy for some slow-cooked meat and a huge selection of American whiskey.
Traditionally working class neighborhoods and home to the White Sox, the South Side has some sketchy parts but also some great cultural neighborhoods. You’ll want a car to get around here — don’t wander off alone, stay away from public transit, and go with a local if you can. Have breakfast at Chicago’s Home of Chicken and Waffles in culturally diverse Bronzeville, then check out US Cellular Field in Bridgeport with a stop at Grandstand to shop for South Side baseball swag. Lunch in ritzy Hyde Park at Medici on 57th and see if you can spot Obama’s home by the University of Chicago campus. From there, head down to Pullman to visit the town-within-a-town historic district created by George Pullman of railcar fame. End your day in the Irish enclave of Beverly with a Freddy Sandwich at Calabria Imports and a five-layer ice cream treat at Rainbow Cone.