The best trip within about five hours of Chicago for each of the next 6 weekends, chosen for kids under 6. Every event links to the official page we checked it on. After the weekends there are 3 day trips that work any weekend.
6 weekends
3 cities
Closest: 2hLast checked against official pages. How we choose
Each ring is one hour of driving from Chicago. Under two hours is an easy day trip; past three, pack the pajamas.
Orange dots are picks on this page. Drive times are normal driving times without traffic.
We don't post event listings for these places, so check the official page for hours and what's on. The numbers match the map.
A public shore path follows about 21 miles of Geneva Lake shoreline, and most visitors walk it in sections.
Galena has a historic Main Street and the Ulysses S. Grant Home, with rolling vineyards in the country around town.
The Dells has more indoor and outdoor waterparks per capita than anywhere else on the planet, with more than 220 waterslides.
Visitors have been coming to the seven villages of the Amana Colonies for over a century for German food and handcrafted goods.
Families can walk the movie diamond in the cornfields and play catch with the Ghost Players, and the field is open year-round.
Indiana's largest state park covers 16,000 acres of hills and ravines, and its tree-lined roads are a fall color hotspot.
3h 30m
about 3 hr 30 min from Chicago
ZooBoo's final weekend, with Halloween fun at the zoo from 2 p.m. through Sunday, Nov. 1.
Past three hours, make it an overnight: drive Friday, go Saturday.
Runs Wednesdays to Sundays through Nov. 1.
Fri Oct 30, Sat Oct 31, Sun Nov 1 · Festivities from 2 p.m.Indianapolis Zoo
See the zoo's ticket page2h
about 2 hr from Chicago
Family Free Day: everyone gets into the Milwaukee County Zoo free on Saturday, Nov. 7. Parking and ride fees still apply.
Everyone gets in free on the first Saturday in November.
Sat Nov 7 · Zoo hoursMilwaukee County Zoo
Free admission; parking and attraction fees still apply2h
about 2 hr from Chicago
Wild Kratts LIVE! plays the Miller High Life Theatre on Sunday at 1 and 5, and BrainExpo, a free hands-on brain science fair for all ages, runs 10 to 5 both days.
Martin and Chris Kratt on stage with the rest of the team on screen, in an all-new creature-power adventure.
Sun Nov 15 · 1 p.m. and 5 p.m.Miller High Life TheatreSee the Pabst Theater Group for ticketsA free hands-on neuroscience festival built for all ages, with real brain specimens and food trucks 11 a.m.–3 p.m. both days.
Sat Nov 14, Sun Nov 15 · 10 a.m.–5 p.m.MCW Alumni CenterFree admission and parking; RSVP requested
2h
about 2 hr from Chicago
Wild Lights opens, plus the Holiday Folk Fair.
Closed Nov. 23–26 and Nov. 29–30. Sunday, Nov. 22 is a drive-thru night.
Fri Nov 20, Sat Nov 21, Sun Nov 22 · 5:30–9 p.m. (gates close 8:15)Milwaukee County Zoo$15 adults and kids 3–12 (early-bird online price through Nov. 8); 2 and under free; parking includedFood, music and dance from dozens of cultures under one roof.
Fri Nov 20, Sat Nov 21, Sun Nov 22 · Fri 2–9 p.m.; Sat 10 a.m.–9 p.m.; Sun 10 a.m.–6 p.m.Exposition Center at Wisconsin State Fair Park, West Allis$13 in advance for ages 8 and up2h
about 2 hr from Chicago
Wild Lights is open Friday and Saturday, with parking included. It's closed Sunday.
Closed Nov. 23–26 and Nov. 29–30. Sunday, Nov. 22 is a drive-thru night.
Fri Nov 27, Sat Nov 28 · 5:30–9 p.m. (gates close 8:15)Milwaukee County Zoo$15 adults and kids 3–12 (early-bird online price through Nov. 8); 2 and under free; parking included
0 min
Chicago is our pick for the whole region this weekend. Kohlights at Kohl Children's Museum runs Friday and Saturday evenings, with early entry from 4:30 p.m.
Opens 11/27; runs through 12/20. Made for kids up to 8.
Fri Dec 4, Sat Dec 5 · Early entry 4:30–7pm; regular 5:30–7pmKohl Children’s Museum$20 early, $18 regular ($15 members)Meijer Gardens' Christmas & Holiday Traditions is open during garden hours and included with admission, so it fits around naps.
Places outside the city that are worth the drive on any weekend. Hours and prices are what the official pages showed when we checked.
Lake Michigan beaches and big sand dunes to climb about an hour from the Loop. The visitor center in Porter is free and a good first stop.
about 1 hr from Chicago · Porter
Most areas open daily 6am–11pm; West and Porter beaches close at 9pm$25 per car for a 7-day passHands-on museum on the bluff above Lake Michigan, aimed at younger kids. Walk-up entry works on regular open days.
about 2 hr from Chicago · St. JosephOpen days 10am–5pm; dates vary, check the calendar$8 per person age 12 months and upCanyons and bluff-top overlooks along the Illinois River, with short trails that start near the visitor center.
about 2 hr from Chicago · OglesbyPark 7am until sunset; visitor center 9am–4pm dailyNo entry fee
Car snacksPack more than you think you’ll need.
StrollerZoo paths and light trails are long for little legs.
Time the napLeave right before nap so the drive does double duty.Overnight bagPast three hours, pajamas beat a 9pm drive home.
Parking cashFree admission days often still charge for parking.
Rain planPick one indoor backup, like a museum, before you leave.Over the next 6 weekends our picks from Chicago are Indianapolis, Milwaukee. Each one is chosen for what's on that weekend, with the dates, times and prices checked on the official pages.
Indiana Dunes National Park in Porter (about 1 hr), Curious Kids' Museum in St. Joseph (about 2 hr), Starved Rock State Park in Oglesby (about 2 hr). Hours and prices are on each card, checked on the official pages.
Milwaukee (about 2 hr), Madison (about 3 hr), Grand Rapids (about 3 hr 30 min), Indianapolis (about 3 hr 30 min), Fort Wayne (about 3 hr 30 min), Toledo (about 4 hr 30 min). Times are normal driving times without traffic.
Lake Geneva (about 1 hr 45 min), Galena (about 3 hr 30 min), Wisconsin Dells (about 3 hr 45 min), Amana Colonies (about 4 hr 45 min), Field of Dreams Movie Site (about 4 hr 45 min), Brown County State Park (about 4 hr 45 min). We don't post event listings for these, so check the official page for what's open before you go.
Sometimes one city really does have the most going on two weekends in a row, like a holiday lights opening followed by a show. We don't rotate cities just for variety.
They're what each official page showed on Oct 29, 2026. Tap through to the official page before you go.