Try a jibarito, the plantain sandwich born in Humboldt Park

For a first visit, the Loop puts theaters, Millennium Park and every L line close, but it is busy on weekdays and quiet at night. River North has the densest mix of restaurants, bars and rooftops and a short walk to the Riverwalk, though bar blocks can be loud on weekends, so ask for a quieter room. West Loop and…

The Palmer House at State and Monroe in the Loop is a Chicago Landmark and a Historic Hotels of America member, with a grand lobby ceiling of 21 panels painted in Paris by Louis Rigal and installed in 1927. Tiffany-designed chandeliers hang in the lobby too. Book it as an experience in itself, and look up as soon as…

The city's free jazz festival fills Millennium Park on Labor Day weekend in early September, with the main stage at the Jay Pritzker Pavilion and extra shows at the Chicago Cultural Center. It grew from a 1974 Duke Ellington tribute and first ran officially in 1979. Bring a chair or blanket for the Great Lawn, though…

The Green Mill Cocktail Lounge at 4802 N. Broadway has been a jazz club since the 1930s and still books live music most nights. Weeknights are easier for a seat, while Friday and Saturday headliners start at 8 pm and a late-night session can run into the early hours. On Sundays, the Uptown Poetry Slam, which started…

Each October the Chicago Architecture Center opens more than 200 buildings across about 30 neighborhoods, free to everyone, from landmark theaters to private clubs and sacred spaces. Most sites run from 10 am to 5 pm, and some open one day only, so use the online directory and pick a few in one neighborhood. Expect…

Founded in 1957, the Old Town School of Folk Music holds concerts at its Lincoln Avenue campus in Lincoln Square, in the 400-seat Maurer Hall and the smaller Szold Hall across the street. The programming runs from folk and singer-songwriters to flamenco, Irish music and mariachi. Check the concert page for upcoming…

Quimby's Bookstore on North Avenue in Wicker Park sells independently published books, comics and zines, and nearly a quarter of its stock is self-published work. It was sold to new owners in spring 2025 and stayed in the same spot. It is a short walk east of the Blue Line Damen stop. Ask staff for local Chicago…

Maxwell Street Market used to run every Sunday, but it now takes place only on a handful of Sundays between May and October, and its footprint around Maxwell Street and Desplaines has changed over the years. Do not plan a free Sunday around it without checking the city's current schedule. If you go, arrive early…