Chicago rewards families who show up with a plan. The city is big enough to feel overwhelming without one, and the best stuff — free zoo, epic lakefront playground, real aerial adventures — doesn't get the marketing budget of Navy Pier. This itinerary uses actual listing data to give you a realistic, day-by-day plan that works.
Best time to visit: Late April through October. Summer is great for the lakefront; avoid the brutal January cold if you're bringing little ones. Weekdays at paid attractions (Museums, Color Factory, Game Show) save money and skip crowds.
Day 1 — Lakefront and Downtown
8:30AM — Millennium Park + Maggie Daley Play Garden
Start early before the crowds arrive. Millennium Park is the entry point — the Bean, the Crown Fountain splash pad (summer), the whole iconic thing. Free. Then walk straight to Maggie Daley Park Play Garden right next door. This is a 3-acre adventure landscape — ship-themed climbing structure, rock climbing wall, mini-golf — not a standard playground. Free. Plan 2-3 hours for both. Budget $15-$30 for food from nearby Millennium Park vendors or pack a lunch.
11:30AM — Museum of Illusions Chicago
Walk or cab to Museum of Illusions Chicago. Nearly 5,000 reviews at 4.7 stars. The Ames room makes family members appear to shrink and grow; the tilted room, hologram gallery, and infinite mirror room are all crowd favorites. Plan 1-1.5 hours. Cost: ~$80-$100 for a family of 4 ($20-$25/adult, $15-$20/child). No on-site food — plan lunch after.
1:30PM — Lunch in the Loop
3:00PM — Amazing Chicago's Funhouse Maze at Navy Pier
Walk to Navy Pier. The funhouse maze works well for the 4-12 age range — mirrored corridors, distorted rooms, puzzle-style passages. It's quick enough to not overstay its welcome. Cost: ~$50-$70 for a family of 4. Budget $10-$25 for Navy Pier parking or take the CTA.
Evening — Dinner and waterfront walk
Day 1 estimated cost: ~$180-$230 (museums + lunch + dinner)
Day 2 — Lincoln Park Zoo and Lakefront
Day 2 is the free day. Seriously — you can spend the entire day and barely spend anything.
9:00AM — Lincoln Park Zoo
Free. The whole thing. Start at the Kovler Seal Pool — below-water viewing panels where seals swim directly at kids at eye level. Move to the Kovler Lion House for lions and snow leopards through glass. Hit the Pritzker Family Children's Zoo for close animal encounters designed for small kids. Walk the Nature Boardwalk — a restored urban pond with herons, turtles, and dragonflies. Plan 2-3 hours. Pack a picnic. CTA Red Line to Fullerton saves $10-$25 in parking.
12:00PM — Picnic at the park
1:30PM — Montrose Point Bird Sanctuary
Take the CTA north to Montrose. Free. Chicago's best urban wildlife encounter — migrating birds funnel through here during spring and fall, making it one of the Midwest's premier birding spots. Combine with Montrose Beach right next to it. Plan 45-90 minutes. Bring binoculars.
3:30PM — Water Playground in Lincoln Park
If it's summer, head back to the Lincoln Park water playground. Jets of water shoot up at unpredictable intervals. Free. Bring a change of clothes.
Evening — Neighborhood dinner (Lincoln Square or Lakeview)
Day 2 estimated cost: ~$40-$60 (packed lunch, CTA passes, dinner)
Day 3 — Adventures and Suburban Escapes
Day 3 picks the activities that require a drive or more planning.
9:00AM — Brookfield Zoo (or Go Ape, depending on your kids)
Option A: Brookfield Zoo — 216 acres, 450+ species. The Dolphin Show is the highlight — genuine awe even for skeptical teens. The Hamill Family Play Zoo has interactive animal exhibits. Plan 3-5 hours. Cost: ~$80-$100 admission, $15-$20 parking, $40-$60 food (or pack your own to cut $40 off). Budget $140-$180 for the full day. This is a full-day commitment — don't pair it with anything else.
Option B: Go Ape Zipline and Adventure Park — For active families with kids who want a physical challenge. Forest canopy zip lines, aerial rope bridges, and tarzan swings. ~$120-$160 for 2 adults + 2 kids. Plan 2-3 hours. Check height and age requirements before booking.
Afternoon (if you chose Go Ape): Funtopia Glenview
Funtopia is a bouldering and climbing wall playground where kids tackle color-coded routes on overhanging walls — not a trampoline park. Rock climbing shoes included. Cost: $80-$130 for a family of 4. Plan 1.5-2.5 hours. In Glenview — easy to combine with Go Ape.
Day 3 estimated cost: ~$155-$200 (Brookfield route) or $200-$290 (Go Ape + Funtopia)
What This Trip Will Cost
| Activity | Family of 4 Estimate | |---|---| | Millennium Park + Maggie Daley Park | Free | | Museum of Illusions | $90 | | Amazing Chicago's Funhouse Maze | $60 | | Lincoln Park Zoo (all sections) | Free | | Montrose Point Bird Sanctuary | Free | | Brookfield Zoo (admission + parking + lunch) | $160 | | Activity Total (Brookfield route) | ~$310 |
Add food ($40-$60/day x 3 days) = $120-$180. Total 3-day trip: $430-$490 for activities and food, before lodging.
Substituting Go Ape + Funtopia for Brookfield Zoo on Day 3 pushes activities to ~$380-$420.
Practical Tips for Your Chicago Family Trip
- CTA saves real money. Red Line covers Lincoln Park, downtown, and Lakeview. A family CTA day pass costs far less than downtown parking ($20-$35).
- Metra to Braeside eliminates Botanic Garden parking. If you add a Botanic Garden visit, the train is the move.
- Book Color Factory in advance. If you want to swap it in for the Funhouse Maze, tickets sell out on weekends. It's $30-$38/person ($120-$150 for a family of 4) — worth it if you have sensory-friendly kids who love immersive spaces.
- Monday is discounted day at Morton Arboretum for Illinois residents — worth knowing if you extend the trip.
- Brookfield Zoo is a full-day destination. Do not try to pair it with a second major activity. 216 acres will tire everyone out.
- Kids Empire (North Riverside or Kedzie) is a great rainy day or bad weather swap. Free mall parking, 4.9 stars, genuinely impressive play structures.