Chicago’s big, with a vibe of being muscular and solid and proud. Skyscrapers—both modern and of a fantastical 19th century architecture—rise above the stiff winds coming off Lake Michigan. City dwellers are midwestern friendly. Add in a downbeat of jazz and a riverboat cruise, and you’ll be singing “Sweet Home Chicago.”
Home of the deep dish
Chicago-style pizza has high walls to support that chunky tomato sauce and—let’s be honest—an ungodly amount of cheese. You can have a revelatory experience at Nancy’s, which claims invention of the stuffed pizza; one of Giordano’s many locations, which began with a recipe from Turin, Italy, brought over by immigrants; or the famous Gino’s East, which will ship you a pizza if you can’t stop thinking about it back home.
The food doesn’t end
You can start the day with breakfast at Yolk on the West Loop, then proceed to a “wet beef” sandwich at Portillo’s or Johnnie’s Beef, enjoy award-winning barbecue at Smoque, and find sweetness at Honey Butter Fried Chicken with its humanely raised, antibiotic-free Amish chickens. You’ll need a reservation for Virtue Restaurant, where African American owner and chef Erick Williams offers southern staples like blackened catfish and gumbo. You’ll have to end the meal with We Finally Got a Piece of the Pie, described as “sweet potato pie as it should be.”
For a splurge dinner, check out Oriole, where the Japanese-influenced tasting menu earned two Michelin stars, or the Purple Pig, where “cheese, swine, and wine” are prepared by a James Beard Award– winning chef.
Museums abound. Three not to miss are the Field Museum, especially if you’re a dinosaur fanatic; the Art Institute of Chicago, one of the world’s leading fine arts institutions; and the DuSable Museum of African American History, the first independent museum in the United States whose collections are devoted to the history and culture of Africans and African Americans.
Follow the Obamas
Author Anara Guard says, “A visit to the Hyde Park neighborhood where I grew up will yield these mementos: the home at 5046 S. Greenwood where Barack and Michelle raised their daughters before moving to the White House; a plaque on a rock that celebrates their first date and kiss—I kid you not—at 53rd and Dorchester; and their favorite booth at The Medici restaurant at 1327 E. 57th Street, the only one where they could stretch their long legs, which is now covered in celebratory graffiti.”
Cycle through town
Chicago’s flat terrain and wide roads make for a great urban ride. Lyft’s Divvy Bikes system boasts 600 stations with 6,000 bikes; use the app to locate an available bike. Popular rides closed to vehicular traffic include the north and south Lakefront trails and “the 606,” a former elevated rail line that has been paved over.
Whatever floats your boat
Anyone who has taken the Chicago Architecture Foundation Center River Cruise mentions it as a highlight of a visit. Aboard a 250-passenger cruiser, you’ll drift down the Chicago River as a docent points out spectacular architecture and tells the city’s history.
Famous for jazz
Chicago’s Cultural Affairs Department proclaimed 2020 the “year of Chicago music,” focusing on the gospel, urban blues, modern jazz, and more that created the city’s music scene. Pick from venues like Winter’s Jazz Club and FitzGerald’s Nightclub. The Green Mill hosts live jazz every night. DW