This Weekend in Chicago, IL
Nov 6–Nov 8· Snowy, 48°/34°F
Best free zoo in the country. Also: everything else.
🆓 Free this weekend
Ping Tom Memorial Park
Chinatown
A beautifully designed park in Chinatown with a free outdoor pool (summer), outdoor basketball courts, a playground, and access to a Chicago River kayak launch. The river-edge path connects to the Riverwalk. Free to enter. One of the most underrated parks on the South Side.
Maggie Daley Park Skating Ribbon
Loop
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.
Garfield Park Conservatory
Garfield Park
One of the largest and most stunning plant conservatories in the country — and it's completely free. The Fern Room is a humid, lush rainforest. The Palm House has 70-foot trees. Perfect for a winter date when you need to feel warm and alive. Go on a weeknight evening when it's nearly empty.
Portage Park Olympic-Size Pool
Portage Park
50-meter Olympic-size indoor pool. Lap swim, open swim, lessons, water aerobics. Free or low-cost through the Park District. Open year-round.
Oz Park
Lincoln Park
Wizard of Oz-themed park with statues of the whole crew -- Dorothy, Tin Man, Scarecrow, Cowardly Lion. Big playground with modern equipment, sports fields, artificial turf area. Free. Lincoln Park families treat this as their backyard.
Grant Park Skate Park
South Loop
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.
🌳 Get outside
Lincoln Park Zoo
Lincoln Park
Free zoo, open every day of the year. Regenstein African Journey, Pritzker Family Children's Zoo with a climbing area, Farm-in-the-Zoo with daily feedings. ZooLights in winter. No excuses not to go.
Brookfield Zoo Chicago
Brookfield (suburb)
450+ species on 216 acres. Hamill Family Play Zoo lets kids pretend to be zookeepers. Butterflies! exhibit, dolphin show, and seasonal events (Holiday Magic, Dinos Everywhere). Free parking Tuesdays and Thursdays in winter. 14 miles west of downtown -- worth the drive.
Navy Pier
Streeterville
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.
Oz Park
Lincoln Park
Wizard of Oz-themed park with statues of the whole crew -- Dorothy, Tin Man, Scarecrow, Cowardly Lion. Big playground with modern equipment, sports fields, artificial turf area. Free. Lincoln Park families treat this as their backyard.
Millennium Park McCormick Tribune Ice Rink
Loop
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.
👨👩👧 With kids
Chicago Park District - Indoor Pools (Multiple Locations)
Citywide
The Chicago Park District operates 50+ pools across the city, including indoor pools open year-round. Family swim sessions, lap swim, and swim lessons are available at no cost. Portage Park, McFetridge, and Welles Park all have indoor pools. The outdoor pools expand to 7-day-a-week service in summer 2026.
Shedd Aquarium
Museum Campus
32,000 animals. The Polar Play Zone is the spot for kids under 5 -- penguin habitat and touch pools. Abbott Oceanarium has beluga whales and dolphins. Illinois residents get discounted admission on certain days.
Chicago Children's Museum
Streeterville
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.
Wicker Park - Playlot Park
Wicker Park
Renovated playground with separate toddler and older-kid sections. Splash pad in summer. Ball fields. Fieldhouse with free Park District programming -- arts, sports, after-school. A neighborhood park that actually delivers.
Chicago Children's Theatre
West Loop
Dedicated children's theater company in the West Loop running professional productions for ages 0 through teens. The 2026-27 season includes Carmela Full of Wishes, The Beatrix Potter Holiday Party, and The Very Hungry Caterpillar Show. Tickets around $42 (lap seats for under-18-months are $13). $20 lottery tickets available each weekend. Also runs acting classes and camps. Free parking lot on-site. Blue Line to Racine stop.
🍷 Date night
Art Institute of Chicago
Loop
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.
Pat's Pizza
Lincoln Park
Tourists argue about deep dish. Chicagoans eat tavern-style thin crust cut in squares, and Pat's has been doing it since 1950. Ultra-thin, ultra-crispy, no-frills. Three generations of the same family. This is the pizza you order when you actually live here.
The Second City
Old Town
Tina Fey, Steve Carell, and an absurd number of famous comedians came out of this building. Mainstage runs original revues; smaller stages have emerging talent. Ten Dollar Comedy shows are the budget move. Nightly.
Buddy Guy's Legends
South Loop
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.
Museum of Contemporary Art Chicago
Near North Side
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.
🎭 Entertainment
Art Institute of Chicago
Loop
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.
Pat's Pizza
Lincoln Park
Tourists argue about deep dish. Chicagoans eat tavern-style thin crust cut in squares, and Pat's has been doing it since 1950. Ultra-thin, ultra-crispy, no-frills. Three generations of the same family. This is the pizza you order when you actually live here.
The Second City
Old Town
Tina Fey, Steve Carell, and an absurd number of famous comedians came out of this building. Mainstage runs original revues; smaller stages have emerging talent. Ten Dollar Comedy shows are the budget move. Nightly.
Buddy Guy's Legends
South Loop
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.
Museum of Contemporary Art Chicago
Near North Side
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.