Things to Do in Near North Side

Free for IL residents first Sunday and Monday of each month. On Navy Pier.

Three floors on Navy Pier: dinosaur dig, water play, building zone, art studio. Ages birth to 10. Kids under 1 free. Illinois residents get free admission on the first Sunday and Monday of each month.

700 E Grand Ave, Chicago, IL 60611 · Daily 10am-5pm, Thu until 8pm · indoor · Ages 0–10

Free to walk around. Free fountain for kids. Fireworks Wed + Sat nights in summer.

Free to walk the pier. Centennial Wheel for skyline views and Pier Park carnival rides cost extra. The Polk Bros Park fountain is free and kids will not leave it in summer. Fireworks on summer Wednesday and Saturday nights.

600 E Grand Ave, Chicago, IL 60611 · Sun-Thu 10am-8pm, Fri-Sat 10am-10pm (seasonal)

Improvised Shakespeare Company performs here. Cheaper and weirder than Second City.

Helped pioneer long-form improv. Multiple stages, nightly shows, including the long-running Improvised Shakespeare Company. Also teaches improv classes at all levels. More experimental and performer-driven than Second City, and cheaper.

1501 N Kingsbury St, Chicago, IL 60642 · Shows nightly, schedule varies · indoor

World's largest magic venue. Inside the historic McCormick Mansion. Opened 2026.

A brand-new immersive magic experience inside the historic McCormick Mansion on Michigan Avenue, opened April 2026. Multiple rooms, each with a different style of magic and illusion. The production value is high and the building itself is part of the show. Cocktails available. Unlike anything else in Chicago.

430 N Michigan Ave, Chicago, IL 60611 · Show times vary, check schedule · indoor

Live jazz since 1951. Two sets nightly. $10-15 cover. Downtown location.

Live jazz since 1951 in the River North area. Two sets nightly with a $10-15 cover. Full restaurant and bar menu. More accessible and less touristy than some of the bigger-name clubs. A solid option for catching jazz without committing to a late night in Uptown.

11 E Hubbard St, Chicago, IL 60611 · Mon-Sat 5pm-1am, Sun 5pm-12am · indoor

Free on Tuesdays for IL residents. Rooftop sculpture garden. Wednesday late nights.

Contemporary art from 1945 to present across three floors, plus a sculpture garden with skyline views. Free admission for Illinois residents every Tuesday. Wednesday late nights (5-9pm) often include free programming. The gift shop is above average. Located steps from the Magnificent Mile.

220 E Chicago Ave, Chicago, IL 60611 · Tue 10am-9pm, Wed-Sun 10am-5pm, closed Mon

Intimate jazz room two blocks from Navy Pier. $7-20 cover. One-drink minimum.

A dedicated jazz listening room in Streeterville, two blocks from Navy Pier. Cover runs $7-20 depending on the night and whether you sit at the bar or on the floor. One-drink minimum. The room is small and focused — this is for people who actually want to listen to jazz, not use it as background noise.

465 N McClurg Ct, Chicago, IL 60611 · Wed-Thu 5pm-10:30pm, Fri-Sat 6pm-11:30pm, Sun 4pm-9:30pm, closed Mon-Tue · indoor

Live jazz Fri & Sat — no cover. Prime rib and steaks in a swanky jazz-era room.

A swanky supper club in River North with live jazz in the lounge on Fridays (7:30-11pm) and Saturdays (8-11:30pm) — no separate cover charge. Prime rib, steaks, and seafood. The jazz comes with the dinner, not on top of it. Dress up a little. This is old-school Chicago dining.

350 N State St, Chicago, IL 60654 · Tue-Thu 5pm-9pm, Fri-Sat 5pm-10pm dining / 5pm-11:30pm lounge · indoor

Chicago dog, Italian beef dipped, and a chocolate cake shake. That is not a health food order. That is a Portillo's order.

Fast-casual Chicago institution. The Chicago-style hot dog (no ketchup, ever) is $5.29. The Italian beef is the real draw — order it dipped with hot giardiniera. The chocolate cake shake is a milkshake blended with an entire slice of chocolate cake. Multiple locations; the River North one draws tourists but moves fast.

100 W Ontario St, Chicago, IL 60654 · Sun-Thu 10:30am-11pm, Fri-Sat 10:30am-midnight · indoor