Is Chicago family-friendly?

The Museum Campus on Lake Michigan's south shore puts three major institutions within 800 meters of each other. The Field Museum of Natural History, open since 1893, has Sue the T. rex skeleton on the main floor, and kids under 3 tend to lose their minds at the sheer size of it. General admission runs $30 adult, $21 child (3-11), free for under 3. Shedd Aquarium sits next door. The beluga whale exhibit smells like cold salt water and sounds like a submarine movie, which is to say, exactly what a 5-year-old wants. Tickets are $44.95 adult, $35.95 child. The Kenneth C. Griffin Museum of Science and Industry, 10 km south in Hyde Park (founded 1933), is the one your kids will ask to go back to. The coal mine descent takes you into a loud, dark, rattling elevator cage. The U-505 submarine tour costs $25 extra per person but puts you inside an actual captured World War II vessel where you can feel the cramped steel walls. Plan 3-4 hours per museum. Doing two in one day is possible. Three is a meltdown guarantee.

Maggie Daley Park, directly east of Millennium Park, opened in 2014 and has the best free playground in any major American city. That is not hedging. The Play Garden section splits into areas for ages 2-5 and 6-12, with a 40-foot climbing wall, rope bridges, and a slide crater that is basically a skate park made of smooth concrete. In winter, the skating ribbon (not a rink, a winding path) costs $16 per skater including rental. Cloud Gate sits 5 minutes west, and toddlers like touching its cool, curved surface more than photographing it. Stroller verdict for Chicago is good. The Lakefront Trail runs 30 km of flat, paved surface from Edgewater to South Shore. CTA trains are the weak spot. Only about 100 of 145 stations have elevators, and the older ones involve steep stairs with no ramp. Check the CTA accessibility map before planning a route. Buses kneel and have ramp access, so they tend to be the better stroller option. Taxis and rideshares fit most umbrella strollers in the trunk without folding.

Kid food in Chicago is easier than most big cities. Lou Malnati's deep-dish pizza (the Buttercrust, around $18 for a small) is the one chain where the kids' menu does not feel like an afterthought. Portillo's on Ontario Street sells hot dogs, and the chocolate cake shake is the kind of sugar bomb that buys you 45 minutes of cooperative walking afterward. For allergy-conscious families, the Chicago Diner in Logan Square and Lakeview has been vegan since 1983 and labels every allergen. In Lincoln Park, R.J. Grunts has served a salad bar and burgers since 1971, and highchairs appear without asking. Grocery backup matters. The Whole Foods at 1550 N Kingsbury in Lincoln Park has a hot bar and changing tables in the restroom, which is the specific combination tired parents actually need. Navy Pier restaurants are overpriced and slow. If you end up there, Giordano's at the pier is the least painful option at about $22 for a small stuffed pizza.

Skip Willis Tower's Skydeck with kids under 5. The elevator ride is 60 seconds and the glass Ledge boxes have a 30-minute wait on summer weekends, which means your toddler peaked emotionally in the elevator and is now screaming through the queue. The 360 Chicago observation deck at 875 N Michigan (the former John Hancock Center) is less crowded and has a bar, which at least means one parent can sit. Lincoln Park Zoo is free, open 365 days a year, and has clean changing stations in every restroom building. It takes 2 hours at a preschooler's pace. The zoo's Cafe at Wild Things serves $4 milk boxes and $8 grilled cheese. Summer in Chicago means 28-32°C days with 70-85% humidity along the lake. Sunscreen and water bottles matter more than jackets. Winters drop to -10°C or colder in January, and wind off Lake Michigan adds a bite that small faces feel fast. The 8-week window from late May through mid-July is when the weather cooperates and the school-trip crowds have thinned.