As a native Chicagoan, I’ve spent a lifetime exploring the surrounding area — suburbs reachable by public transit as well as small towns within a few hours’ drive of the Windy City. From glistening lakeshore towns to historic sites to natural wonders, these are some of my family’s favorite day trips from Chicago.
Day Trips in Illinois
Growing up, we tended to hug Lake Michigan on our family road trips, mostly heading into Wisconsin or Michigan. But once I had kids, we discovered the wonders of what we Chicagoans call “Downstate Illinois.”
Starved Rock State Park
This lovely spot two hours from Chicago was our go-to hiking spot when the kids were young. Lining the shores of the Illinois River, Starved Rock State Park has 13 miles of trails that wind along fascinating rock formations you wouldn’t expect to find in the flatlands of Illinois. The area was formed more than 425 million years ago during an intense warming period after the glaciers melted and left behind soft sandstone in the Illinois River Valley.
Visit here in spring when the winter thaw leads to waterfalls in all 18 canyons or in the fall when the leaves are at their most colorful. It’s one of the best places to see gorgeous fall colors in the Midwest.
SheBuysTravel Tip: Bring a change of clothes and the kids’ rain boots if you visit in the spring — they will get wet and muddy!
If you plan to spend the weekend, there are campground options, as well as the lovely and historic Starved Rock Lodge that was built by the Civilian Conservation Corps in the 1930s. But the kids might prefer the water park at nearby Grand Bear Resort.
Matthiessen State Park
This is the lesser-known cousin of Starved Rock. Located just a few miles south, Matthiessen has similar geology and terrific hiking trails. It’s a don’t-miss spot if you’re visiting the area in mid to late July. That’s when the sunflower fields are in full bloom.
Rockford
OK, Chicago snob here. I grew up making fun of Rockford. That ended once I visited when my kids were 8 and 10. I had to pry them out of the Discovery Center Museum! Mostly indoor, it has multiple levels full of hands-on learning fun. But I did pry them away so my dinosaur-loving family could head to the Burpee Museum of Natural History to meet Jane, the juvenile T-rex. We spent so much time there that we never made it to the Rockford Art Museum.
If you’re looking for outdoorsy things to do in Rockford in the summer, head to The Anderson Japanese Gardens. While it might seem a little odd to find a Japanese garden in the heart of the Midwest, this superbly zen spot comes courtesy of a Rockford businessman. Inspired by a visit to a Japanese Garden in Portland, Oregon, John Anderson decided to transform his swampy backyard along Rockford’s Spring Creek into a peaceful, Japanese-style landscape. For a more tropical experience, try Nicholas Conservatory and Gardens.
Oak Park
Just a 20-minute L line ride on the Green Line from downtown Chicago, Oak Park is the first suburb west of the city and it’s a mecca for architecture lovers who flock there to see the Frank Lloyd Wright Home and Studio.
Chances are that won’t get your kids too excited. Mine weren’t when they found out they would be visiting the Home and Studio on a school field trip. I had always wanted to see it, so I volunteered to chaperone. I listened to the 3rd and 4th graders complain all the way there. Then I watched with a smile as they were engrossed in stories about Wright’s kids having pillow fights over the partition wall that separated the boys’ and girls’ bedrooms. And I said no when my kids begged me to buy them a set of the building blocks Wright used as a kid that set him on his life’s path.
Chicago Botanic Garden
My brother-in-law lives a half mile from the Chicago Botanic Garden in north suburban Glencoe, so I’ve visited enough times that I nearly failed to include it in this roundup. It feels almost like a neighborhood park. But it is So. Much. More. The Botanic Garden is 385 acres of gardens and natural areas and is home to a renowned Bonsai Collection.
Take kids in the fall to see the model railroad with its scale models of US landmarks. Or visit during the holidays to see one of the best Christmas lights displays in the Midwest. Before you go, download the free Model Railroad BINGO game to play with the kids.
SheBuysTravel Tip: Strollers are not allowed, so plan to bring a Baby Bjorn or some other babywearing device for kids who are too young to walk the entire time you’re visiting.
Morton Arboretum
Located in west suburban Lisle, the Morton Arboretum is extra popular in the fall when Chicagoans drive through this “great outdoor museum” of trees to see the fall colors.
But I’ve been there to walk the 16 miles of trails (it’s dog friendly) and even to see a play that moved from one idyllic setting to the next as the play progressed. (Unfortunately, there were a lot of bees that summer and I spent more time watching them buzzing around than I did watching the actors.)
A Children’s Garden aimed at letting kids learn while they’re having fun has two sections: Backyard Discovery Gardens and Adventure Woods, linked by the Central Plaza. Kids can splash through secret streams, climb colossal acorns, and slide down giant tree roots while they learn about plants they might find in their own backyard and beyond.
Gurnee
This town just south of the Illinois-Wisconsin state line is home to Six Flags Great America amusement park. This is where Chicago kids head for thrilling roller coasters and scary Halloween experiences.
Adults, of course, are welcome to join the kids. But the secret Chicago moms know is this: The amusement park is across the street from Gurnee Mills, a giant shopping mall. So if your kids are old enough to do the amusement park on their own and you’re more into shopping than thrills, this is the day trip that works for parents as well as tweens and teens.
Gurnee also is home to a Great Wolf Lodge indoor waterpark, always a hit with my kids.
Skokie
This northern suburb is home to the third-largest Holocaust Museum in the world. The Illinois Holocaust Museum has more than 500 artifacts donated by Chicagoland Holocaust survivors. There’s an authentic German rail car, impressive galleries and contemplative spaces, both indoors and out.
Read More: Food and Fun in Charming Galena, Illinois
Wisconsin Day Trips from Chicago
Milwaukee
This small city on the banks of Lake Michigan just 90 minutes north of Chicago is home to one of the best children’s museums in the country — the Betty Brinn Children’s Museum. It’s also home to a gorgeous art museum that is just as beautiful on the outside as it is on the inside. The Milwaukee Art Museum is capped with a moveable sunscreen with a 217-foot wingspan that unfolds and folds twice daily.
With older kids, don’t miss a visit to the terrific Discovery World science museum. When I visited, I saw just as many dads paying with the hands-on exhibits as kids.
Milwaukee is famous for its Summerfest music festival. When I attend, the music was great and plentiful and much of it was included in the festival admission. But the beer was flowing freely and there were lots of overly imbibed visitors. I was there without kids, so I managed just fine. But I would not have been happy and relaxed if I had brought younger kids.
Lake Geneva
Just 85 miles north and a little west of Chicago, Lake Geneva is the summer playground for Chicagoans. The lake is the draw here. You can take a boat ride, lounge on one of the small beaches, or walk a portion of the 26-mile Lake Shore Path to ogle the multi-million-dollar mansions that line the lake.
This is also what passes for a ski resort in the Midwest. The Mountain Top at Grand Geneva Resort & Spa has 20 downhill ski runs, complete with chair lifts.
SheBuysTravel Tip: The best way to see the lake is via the U.S. Mail Boat Tour. It’s just what it sounds like — mail delivery via boat. The post men and women literally jump off the boat to deliver the mail, then hop right back on — just the way it’s been done for a hundred years. Except now tourists can ride along.
Elkhart Lake
This tiny lakeside town lacks the big tourist draw of Lake Geneva, but that makes it an even better destination, if you ask me. Elkhart Lake offers plenty of small town charm and its own brand of luxury at the lakefront Osthoff Resort. It’s been one of my family’s favorite Midwest destinations for years.
It’s 150 miles north of Chicago, which makes it a stretch for a day trip. Besides, you’ll want to spend at least one night at the Osthoff. The condos are luxurious and the resort offers lots of fun activities. You can rent a tandem bike and pedal your way around the area. (Or, if you’re like my husband and me, you can try — and then turn in the tandem and rent two regular ol’ bikes instead.) My kids loved the horse-drawn hay ride, swimming in the warm lake waters and the resort pool.
Madison
Also 150 miles from Chicago, Madison can be a stretch as a day trip from Chicago. But it’s definitely worth a visit. The state capital is home to the University of Wisconsin-Madison (go, Badgers!), which sits on the shores of Lake Mendota. It’s a college town, which means the area is filled with bars and affordable food options.
Drag the kids along on a free tour of the State Capitol building. They’ll be a little bored, but seeing the architecture is worth putting up with some sighs from bored kids.
On the sidewalks that ring the capitol building is one of the best farmers’ markets I’ve ever seen. Buy the kids some fresh Wisconsin cheese curds and watch their faces light up when the cheese curds squeak as the kids bite into them. The squeak proves they’re fresh! The farmers’ market sets up each Saturday morning from mid-April through the first week in November. It claims to be the largest producer-only farmers’ market in the U.S.
Indiana Day Trips from Chicago
Indiana Dunes National Park
I grew up spending hot summer days at the Indiana Dunes National Lakeshore. It became the 61st US National Park in 2019 when 15 miles of the lake shore were designated a national park. It didn’t change the experience, though. It’s still an incredible natural resource, with miles of trails for hiking and biking and wide open waters for swimming, kayaking, canoeing and rafting. (Beware: Lake Michigan waters can be coooooold!)
The lakeshore is a year-round attraction, with gorgeous winter vistas across the water and the hiking trails open for walking and cross-country skiing.
It’s a short 45-minute drive from Chicago to Indiana Dunes. At the end of a day at the beach, head to Chesterton or Michigan City for dinner with a craft beer at one of the family-friendly spots that are popping up all over.
Indianapolis
The Indiana state capital is 185 miles southeast of Chicago, so not really a day trip option. But it’s well worth a visit for a weekend getaway.
The city was a sleepy town when I was growing up, but today it’s a thriving metropolis with a vibrant downtown, great pro and semi-pro sports, the best children’s museum in the country and lots of fun free things to do with kids.
Michigan Day Trips from Chicago
Southwest Michigan
Chicagoans flock to the towns that hug the southwest Michigan lakeshore — from New Buffalo to Saugatuck — for the wide sandy beaches and lake town vibe. But the area is also a rural and agricultural gem with wineries, u-pick farms, horseback riding and farm-to-table foodie fun.
While the tourist draw is the “big lake” — Lake Michigan — the state is dotted with small inland lakes perfect for kayaking, canoeing, rafting and swimming. If you happen to have your own kayak or canoe, strap it to the roof of the car and bring it along. Most lakes have public access ramps for launching small boats.
Holland
My parents piled us in the car one spring to make the 150-mile trek to Holland for the Tulip Time Festival. I have vivid childhood memories of a looming windmill, what felt like miles of brightly colored tulips and the wooden shoes I talked my dad into buying. I’m sure he regretted it every minute I spent clomping across our hardwood floors until I outgrew those wooden shoes!
The Dutch-inspired town is home to more than 5 million tulips blooming throughout the town and the tulip festival in early May wins accolades every year.
Kalamazoo
My now young adult children live in Detroit, so our road trips there take us right past Kalamazoo. Each time, my husband and I share the memory of taking our son and his best pal there to visit the Air Zoo. This world-class, Smithsonian-affiliated aerospace and science museum had a flight simulator! The boys, then both 13, had to be dragged out at the end of the day so we could drive home.
These days, my hubby longs to make a stop in Kalamazoo to tour the Gilmore Car Museum. It claims to have one of Michigan’s largest collections of classic and vintage automobiles.
