Things to Do in The Loop

Free. Climbing walls, slides, skating ribbon in winter. Regularly called the best playground in the country.

Play garden with slides, climbing walls, bridges, and a separate toddler area -- all free. Skating Ribbon in winter (rentals available). Mini golf in summer. Fieldhouse with free programming. Parents regularly lose two to three hours here without meaning to.

337 E Randolph St, Chicago, IL 60601 · Daily 6am-11pm · outdoor

Entire floor dedicated to kids. Free storytime, crafts, STEM -- daily.

Whole floor for kids: free storytime, craft programs, STEM activities, and a play area. Thomas Hughes Children's Library runs daily programming. Every Chicago Public Library branch also runs free kids programs -- check your local branch.

400 S State St, Chicago, IL 60605 · Mon-Thu 9am-9pm, Fri-Sat 9am-5pm, Sun 1pm-5pm · indoor

Free 1.25-mile riverwalk. Play fountains in summer. Kayak rentals. Architecture boat tours.

1.25-mile riverwalk, free to walk. Public art, seasonal play fountains kids love, kayak rentals, and architecture boat tours. McCormick Bridgehouse at the east end is worth a stop if your kid asks how bridges work. Free, year-round.

E Riverwalk S, Chicago, IL 60601 · Daily 6am-11pm (May-Oct for full amenities) · outdoor

Giant faces spit water on your kids. Free. They will get soaked.

Two 50-foot glass towers project video faces of Chicagoans that periodically 'spit' water into a shallow reflecting pool. Kids splash around for hours. Free, no reservation, open May through October. Bring a towel and a change of clothes. One of the most fun free things in the city for kids under 10.

201 E Randolph St, Chicago, IL 60601 · May-Oct, fountain active 6am-11pm · outdoor

Free skate park. Concrete ramps, rails, quarter pipes. Helmets recommended.

Free outdoor skate park in Grant Park near the lakefront with concrete ramps, grinding rails, quarter pipes, and a gap jump. Open to skateboards, scooters, and rollerblades. All skill levels welcome. Helmets and pads recommended. Best for kids 8 and up who have some experience.

360 S Columbus Dr, Chicago, IL 60605 · Daily 6am-11pm · outdoor · Ages 8+

Free ice skating under the Bean. Just bring your own skates or rent there.

Free skating rink right beneath Cloud Gate ("The Bean"). Mid-November through mid-March. Skate rental available for a fee. No reservations -- first come, first served.

201 E Randolph St, Chicago, IL 60602 · Daily 12pm-8pm (seasonal, Nov-Mar) · outdoor

Not a rink -- a winding quarter-mile skating path. Free with your own skates.

Quarter-mile winding skating ribbon -- more of a path than an oval rink. Free if you bring your own skates; rental available. Mid-November through mid-March. Connected to Millennium Park via the BP Pedestrian Bridge.

337 E Randolph St, Chicago, IL 60601 · Daily 12pm-8pm (seasonal, Nov-Mar) · outdoor

$35 day pass. Climbing, yoga, fitness, and a coworking lounge. West Loop.

30,000 square feet in the West Loop. Bouldering, top-rope, lead climbing, fitness area, yoga classes, and a coworking lounge. $35 day pass, no membership required. Beginner intro packages include gear rental and a lesson.

100 S Morgan St, Chicago, IL 60607 · Mon-Fri 6am-11pm, Sat-Sun 8am-10pm · indoor

Free outdoor climbing up to 40 feet. Bouldering, lead, and top-rope. Downtown.

A soaring outdoor climbing wall reaching up to 40 feet, divided into beginner and advanced sections with bouldering, lead-harnessed, and top-rope climbing. Free. Open seasonally (weather permitting). Harnesses and helmets provided. One of the only free outdoor climbing facilities in any major US city.

337 E Randolph St, Chicago, IL 60601 · Seasonal, daily 10am-7pm (weather permitting) · outdoor

Free tennis with the skyline behind you. Six courts. First come, first served.

Six outdoor hard courts in Maggie Daley Park with the downtown skyline as your backdrop. Free, first-come, first-served. No reservation needed. Well-maintained and popular for casual play on summer mornings and evenings. Also has a mini-golf course nearby.

337 E Randolph St, Chicago, IL 60601 · Daily dawn to dusk · outdoor

American Gothic, Nighthawks, Seurat's Sunday -- all here. Kids under 14 free. Chicago teens under 18 free.

American Gothic, Nighthawks, A Sunday on La Grande Jatte. The Renzo Piano Modern Wing is worth the trip for the architecture alone. Kids under 14 always free. Chicago teens under 18 also free.

111 S Michigan Ave, Chicago, IL 60603 · Daily 11am-6pm, Thu until 8pm · indoor

The marquee sign. The grand staircase. $32 tour takes you backstage.

1921 movie palace with the marquee sign everyone photographs. Now hosts concerts, comedy, and special events. The $32 tour (1 hour) takes you through the French Baroque interior, grand staircase, and backstage.

175 N State St, Chicago, IL 60601 · Tour at 12pm, show times vary · indoor

Free concerts all summer. Frank Gehry bandshell. Bring a blanket and a picnic.

Frank Gehry bandshell in Millennium Park. Free concerts all summer -- Summer Music Series on select Mondays and Thursdays, Grant Park Music Festival (classical) June through August, Chicago Jazz Festival over Labor Day weekend. Bring a blanket, picnic on the Great Lawn.

201 E Randolph St, Chicago, IL 60601 · Park open daily 6am-11pm, concerts typically 6:30pm-9pm · outdoor

Buddy Guy's own club. Live blues nightly. The man himself plays every January.

Buddy Guy's own blues club in the South Loop. Live blues every night -- local acts during the week, bigger names on weekends. Buddy Guy himself does a multi-night residency every January. Cajun and Southern food menu. Two stages. If Kingston Mines is the tourist-friendly option, Legends is the real deal.

700 S Wabash Ave, Chicago, IL 60605 · Mon-Thu 11am-2am, Fri-Sat 11am-3am, Sun 12pm-2am · indoor

Chicago's oldest theater. $15 tix-at-six rush. Collaborations with David Byrne.

Chicago's oldest and largest nonprofit theater, founded in 1925. Two stages in the Loop presenting new plays, musicals, and Chicago premieres. The 2026 season includes a David Byrne collaboration at the Reid Murdoch Building. $15 tix-at-six rush tickets available day of show.

170 N Dearborn St, Chicago, IL 60601 · Box office daily 12pm-5pm, show times vary · indoor

The building tour that launched a thousand architecture buffs. Boat tours from $47.

Home base for the Chicago Architecture Foundation River Cruise -- the most popular tour in the city. Also has exhibits on Chicago's skyline, neighborhoods, and building history. The boat tour ($47+) is the flagship experience, but the center itself ($12 admission) has excellent scale models and exhibits.

111 E Wacker Dr, Chicago, IL 60601 · Daily 10am-5pm, boat tours seasonal

Free skate park in Grant Park. Concrete ramps, rails, quarter pipes. All skill levels.

Free public skate park in Grant Park with concrete ramps, grinding rails, quarter pipes, stair sets, and a gap jump. Open to skateboards, rollerblades, BMX bikes, and scooters. Helmets recommended. All skill levels welcome. Right next to the lakefront trail.

360 S Columbus Dr, Chicago, IL 60605 · Daily 6am-11pm · outdoor

17-course omakase served in a hotel suite — 75 minutes, reservations only.

A 17-course omakase experience served inside a hotel suite at Hotel Julian. Intimate seating for a handful of guests. The chef prepares everything in front of you. 75 minutes. Reservations required and they fill up fast.

Hotel Julian, 168 N Michigan Ave, Chicago, IL 60601 · By reservation only, check availability · indoor

$4 boat ride to Chinatown — cheaper and more fun than a rideshare.

The Chicago Water Taxi runs along the Chicago River from Michigan Ave to Chinatown for $4 per ride. It's a legit transportation option, not a tourist boat — locals use it. The Chinatown stop drops you right at the gate. Runs seasonally.

Michigan Ave at Riverwalk, Chicago, IL 60601 · Mon-Fri 6:30am-8pm, Sat-Sun 10am-8pm (seasonal) · outdoor · May-Oct

Chicago's oldest jazz club — founded 1947. Kids under 12 free at Sunday matinee.

The oldest jazz listening room in Chicago, founded in 1947 by Joe Segal. Two shows nightly (8pm and 10pm), Sunday matinee at 4pm. The Sunday matinee is free for kids under 12 — one of the few kid-friendly jazz experiences in the city. Tickets $25-45 depending on the act.

806 S Plymouth Ct, Chicago, IL 60605 · Mon-Sat shows at 8pm & 10pm, Sun 4pm & 8pm · indoor

Stephanie Izard's flagship. The goat empanadas started a thousand imitations. Still no reservations — walk-in bar seating is the move.

Stephanie Izard's Top Chef-winning flagship on Randolph Row. Shareable plates, bold flavors, the famous goat empanadas. Reservations book up weeks out, but the bar takes walk-ins and the food is the same. Budget $50-80 per person with drinks. The West Loop location that launched a restaurant empire.

809 W Randolph St, Chicago, IL 60607 · Mon-Thu 4:30pm-10pm, Fri-Sat 4:30pm-11pm, Sun 4:30pm-10pm · indoor

Communal seating, Mediterranean small plates, and the chorizo-stuffed medjool dates that have been on the menu since 2003 because removing them would cause a riot.

Mediterranean small plates with communal cedar tables. The chorizo-stuffed medjool dates are legendary — they have never left the menu. Wood-oven focused, naturally wine-friendly. Feels like eating at a friend's very cool dinner party. $35-60 per person. Weekend brunch is a sleeper hit.

615 W Randolph St, Chicago, IL 60661 · Lunch Mon-Fri 11am-2pm, Dinner Sun-Thu 3:30pm-10pm, Fri-Sat 3:30pm-11pm, Brunch Sat-Sun 10am-2pm · indoor

Two Michelin stars, hidden in an alley. $414 per person tasting menu. This is the splurge.

Two Michelin stars. Hidden down a West Loop alley with no signage. The extended tasting menu from Chef Noah Sandoval runs $414 per person (kitchen table is $474). This is not a casual Tuesday dinner — this is the anniversary, the proposal, the once-a-year blow-the-budget meal. Book weeks in advance via Tock.

661 W Walnut St, Chicago, IL 60661 · Seatings Tue-Sat, times vary by reservation · indoor

Modern pet grooming salon in the West Loop offering full-service grooming, bathing, nail trimming, and spa treatments for dogs and cats. Located in a convenient West Loop location near the 90/94 expressway. Small dogs from $60, large dogs from $90. Also offers de-shedding treatments and puppy grooming introductions.

1010 W Monroe St, Chicago, IL 60607 · Mon-Sat 8am-6pm, Sun 10am-4pm · (872) 320-8457 · indoor

Shoe, leather, and handbag repair in the West Loop. Sole replacement, heel repair, leather conditioning, dyeing, bag restoration. Heel replacement from $25, full resoling from $60. Appointments for complex work.

215 N Aberdeen St, Chicago, IL 60607 · Mon-Fri 10am-6pm, Sat 10am-4pm · indoor