WonderKit
Family trip · Chicago, IL

5 Days in Chicago with Kids

Chicago is big, flat, and walkable in pockets — which makes it tempting to cram, and a mistake to. This plan gives you one main anchor a day with an easy backup and a built-in eat/rest break, paced for a 6- and a 9-year-old who will hit a wall by mid-afternoon no matter how good the museum is.

A quick honesty note: distances between neighborhoods are real, the lake wind is real, and little legs run out before the day does. Each day below is built around a single anchor plus open time — pick the backup over the anchor whenever the morning runs slow, and don’t feel behind. The lakefront museums, parks, and downtown sights are mostly connected by short walks, a bus, or a 10–15 minute ride.

5-day plan10 stopsFamily tripChicago
Planned by Wonder· built from real, checked placesReal places
Make this plan yoursWhat's on now in Chicago

Photo: Kirk Che Reddulus

Jump to a day
Day 1 · The Bean, the fountain, and a playgroundDay 2 · Animals, for freeDay 3 · Under the lakeDay 4 · DinosaursDay 5 · The pier and the water
Day 1

The Bean, the fountain, and a playground

A note from Wonder

The two parks are connected by a flat, stroller-friendly bridge — total walking is gentle and you can stay put for hours. Do the Bean early before crowds build, then let the playground be the long, no-schedule part of the day.

Millennium ParkAnchor

Millennium Park

Start downtown where the photo-ops and the playground sit side by side. Millennium Park is home to Cloud Gate ("the Bean"), the reflective sculpture every kid wants to make faces in, and Crown Fountain, where two video towers cascade water in summer and turn into a free splash pad — bring a towel and a change of clothes. Then cross the BP Bridge to Maggie Daley Park, whose three-acre Play Garden has tube slides, suspension bridges, and a climbing wall for the 9-year-old while the 6-year-old burns energy below.

Millennium Park

Photo: Gustavo Alvarado

Maggie Daley ParkBackup

Maggie Daley Park

If the morning runs slow, skip everything but Maggie Daley Park's Play Garden. It's a destination on its own and easily fills an afternoon — no tickets, no rush.

Maggie Daley Park

Photo: Meng Thao

Eat & rest

This is a picnic-or-grab-and-go day. Pack snacks for the playground, and walk west into the Loop for a casual lunch — deep-dish at a downtown Lou Malnati’s is the classic kid-pleaser, but order ahead since deep dish takes a while to bake.

Day 2

Animals, for free

A note from Wonder

It’s about a 10–15 minute drive or a bus ride north of downtown. Gates open mid-morning; go early, do the loop you care about, and plan to be out by early afternoon before the meltdown.

Lincoln Park ZooAnchor

Lincoln Park Zoo

Lincoln Park Zoo is free, open 365 days a year, and genuinely walkable for short legs — a rare combination that takes the pressure off. Kids this age love the big mammals (lions, gorillas, the polar bear when it's out) and the Farm-in-the-Zoo, where they can get close to goats and cows. Because there's no ticket, you can leave the moment energy drops and not feel like you wasted money.

Lincoln Park Zoo

Photo: Tony's Lists

Nature BoardwalkBackup

Nature Boardwalk

Right next to the zoo, the free Nature Boardwalk is a flat loop around a pond with turtles, ducks, and a great skyline view — a low-key alternative if the zoo feels like too much, or a cooldown lap on the way out.

Nature Boardwalk

Photo: Patrick Malon

Eat & rest

R.J. Grunts (2056 N Lincoln Park W), across from the zoo, is a longtime family burger-and-salad-bar spot that even keeps a stroller valet — an easy place to refuel after a morning on your feet. Then build in real downtime: the zoo neighborhood has plenty of green grass to sit on before you head back.

Day 3

Under the lake

A note from Wonder

The Museum Campus is just south of downtown — a short ride or a longer lakefront walk. Plan a half-day here, not a full one; aquariums are deceptively tiring, and the touch pools and submarine reward slowing down.

Shedd AquariumAnchor

Shedd Aquarium

The Shedd Aquarium, on the lakefront Museum Campus, is the kind of indoor anchor that earns a whole morning. The Polar Play Zone is built for exactly these ages — a kid-sized submarine, a sea-star touch pool, and penguins to waddle past — while the Caribbean Reef and Wild Reef sharks hold the 9-year-old's attention and the beluga whales in the Abbott Oceanarium are the showstopper. Buy timed tickets in advance; it's popular and lines build.

Shedd Aquarium

Photo: Deplorable Rob

Museum CampusBackup

Museum Campus

If tickets are sold out or the kids aren't up for crowds, the Museum Campus lawns and lakefront path offer skyline views, room to run, and a free, low-effort morning. The campus connects the Shedd, the Field Museum, and the Adler Planetarium, so you can pivot if one is too busy.

Museum Campus

Photo: William Fang

Eat & rest

Pack a lunch — the Museum Campus has lawns made for it and views over Lake Michigan. Otherwise the Shedd has on-site cafes. Afterward, head back and keep the rest of the day open; a big indoor morning is enough.

Day 4

Dinosaurs

A note from Wonder

Same Museum Campus as Day 3, so the commute is familiar. Pick two or three halls (dinosaurs plus one more), let the PlayLab be the break, and call it before fatigue sets in — last entry is well before closing, so arrive by mid-morning.

Field MuseumAnchor

Field Museum

A few steps from the Shedd, the Field Museum is a natural-history palace built for dinosaur-obsessed kids. Máximo the Titanosaur greets you in the main hall, SUE the T. rex has a dedicated exhibit, and the Crown Family PlayLab is a hands-on space aimed at younger visitors — a release valve when the 6-year-old needs to touch things instead of look at them. It's huge, so don't try to see it all.

Field Museum

Photo: Masila Freman

Adler PlanetariumBackup

Adler Planetarium

Also on the Museum Campus, the Adler Planetarium sits at the tip of the peninsula with the single best skyline view in the city and sky shows that work for this age range. It’s a smaller, calmer alternative if the Field feels overwhelming — or a short add-on for the walk alone.

Adler Planetarium

Photo: Sanjay Gupta

Eat & rest

Cafes on-site at the Field, or pack a picnic again for the lakefront lawns. Build the afternoon as downtime — two big museum mornings back to back is plenty, and Day 5 is active.

Day 5

The pier and the water

A note from Wonder

Navy Pier is a flat, wide-open, stroller-easy environment — the easiest "let them run" day of the trip. It’s a short ride east of downtown; on a nice day, the lakefront walk out is part of the fun.

Navy PierAnchor

Navy Pier

End on the water. Navy Pier stretches out into Lake Michigan with open space to roam, the Centennial Wheel (a climate-controlled Ferris wheel that's a gentle thrill for both ages), and fountains to chase. Tucked at the pier entrance, the Chicago Children's Museum is three floors of hands-on play — a pretend city, a fossil-digging Dinosaur Expedition, and water-play tables — aimed squarely at kids 1–10. Do the museum first while energy is high, then let the pier itself be the unstructured afternoon.

Navy Pier

Photo: ___C___

Centennial WheelBackup

Centennial Wheel

Skip the museum and let the pier do the work — the Wheel, the fountains, the open promenade, and a snack with a lake view are a full, low-effort day for tired families on the last leg.

Centennial Wheel

Photo: Todd Furr

Eat & rest

Navy Pier has a range of casual, kid-friendly counters and sit-down spots. Keep it simple, grab a treat, and let the last afternoon be slow.

Rainy-day or heat-of-the-afternoon backup (indoors)

Chicago can turn cold-and-windy or hot-and-bright fast, and the lake amplifies both. Keep these indoor options in your back pocket:

  • Chicago Children’s Museum (Navy Pier): three floors of hands-on play for ages 1–10 — the single best bad-weather anchor on this list. (Built into Day 5; pull it forward on a rainy day.)
  • The Field Museum or Shedd Aquarium (Museum Campus): the two big indoor anchors above double as all-weather days — swap them earlier if the forecast turns.
  • Peggy Notebaert Nature Museum (2430 N Cannon Dr, Lincoln Park): a small, kid-focused nature museum whose butterfly haven lets little ones walk among free-flying butterflies — calm, indoor, and near the zoo.
  • Lincoln Park Conservatory (2391 N Stockton Dr): a free, glass-housed tropical greenhouse next to the zoo — a warm, quiet 30 minutes out of the wind on a cold or rainy day.

Where to eat (real spots, clustered)

  • Deep-dish, downtown: Lou Malnati’s (Loop locations) — the classic kid-pleaser; order ahead, deep dish bakes slowly.
  • Burgers & salad bar, by the zoo: R.J. Grunts (2056 N Lincoln Park W) — longtime family spot across from Lincoln Park Zoo, with a stroller valet.
  • Museum Campus: pack a picnic for the lakefront lawns, or use the on-site cafes at the Shedd and Field Museum.
  • Navy Pier: a range of casual counters and sit-down spots — easy to keep simple with kids.
  • Sweet treat, citywide: Garrett Popcorn Shops — the cheddar-and-caramel "Chicago Mix" is a portable, only-here souvenir snack.

Make this Chicago plan yours

Tell WonderKit your dates and who's coming, and we'll rebuild this around your group in about a minute — everyone votes on the plan, and costs split automatically. One subscription, the whole group.

Start planning — free

One of 15 ready-made WonderKit plans across 15 cities

No credit card · ready in about a minute

Keep exploring