The green Chicago River on St. Patrick’s Day. All photography is ours.
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Illinois with Kids
If you’re planning a weekend in Chicago with kids, take the train in from O’Hare, stay downtown, and skip the rental car. Our first trip was a Labor Day weekend to see how much we could pack in, and we’ve been back several times since. The museums are the best cluster in the country, and the lakefront is free.
Ask our kids and they’ll tell you to start with four things – the Shedd Aquarium, the Skydeck ledge, Sue at the Field Museum, and some deep dish pizza.
Destination guide · Updated November 2026 · Last visited April 2026
Best months
May–June, Sept–Oct
National parks
0 + 8 NPS sites
Fly into
ORD · MDW · SPI
How long
A long weekend in Chicago
Book ahead
American Girl Cafe · Skydeck · Cubs at Wrigley
We’ve done Chicago a few times now. The first trip was a Labor Day weekend. We took the train from O’Hare to downtown, checked in to the hotel, and started with Rick Bayless’ take on Mexican for dinner because he’s a fellow Okie making amazing Mexican food in Chicago. Sunday was brunch at the American Girl Cafe, then 360 Chicago across the street with the VIP line. The Art Institute, the Field Museum, the Skydeck, and Giordano’s filled the rest of the weekend. We’ve added the Shedd and the architecture cruise on later trips.
As far as big cities go, Chicago is one of our favorites. The food is great, the museums are the best anywhere, and the views are stunning. For something extra, try visiting over St. Patrick’s Day. No city does it better.
Hot take: Pequod’s has the best deep-dish pizza in town.
Your Illinois guide
Enjoy exploring Illinois with kids!
Keep scrolling for the essentials, three road trips, and where to stay.
Essential Illinois
Why we love Illinois
We think you’ll love it too.
Illinois is where we’d send a family that wants a big-city weekend with the best museums anywhere. Illinois is mostly Chicago for visiting families, and Chicago is more than enough. If you can, venture out of the city to explore things like the Pullman National Historical Park. Although not technically in Illinois, Indiana Dunes National Park is only about an hour away. If you need a roller coaster fix, Six Flags Great America is just north of the city.
A weekend in Chicago Guide
Our full plan covers the museums, the towers, and the food. It shows you how to fit it all into a long weekend without a car.
American Girl Chicago Guide
We had Sunday brunch at the flagship store, and Cadence saved up her allowance for a new doll and smiled all day. It’s a splurge we’d pay for again.
Skydeck Chicago Guide
The glass ledge on the 103rd floor of Willis Tower is the photo the kids will want. Book timed tickets ahead.
The Field Museum Guide
Sue the T. rex and the mummies can fill a whole afternoon at the Field Museum. It’s the best of the big three museums for kids who love dinosaurs.
And the rest we’d cross the state for
360 Chicago Guide
360 Chicago is at the top of the Hancock building, across the street from American Girl. We went right after brunch and breezed through with the VIP line.
The Art Institute Guide
The kids recognized the paintings from Ferris Bueller’s Day Off (Bueller? Bueller?), and that was enough to get them through the galleries.
Shedd Aquarium Guide
The Shedd is the most engaging stop on the museum campus for younger kids. The beluga tank alone is worth the ticket.
Navy Pier Guide
Navy Pier has the Ferris wheel and the Children’s Museum, and the architecture cruise leaves from the dock. It’s touristy, but the kids won’t care.
Pullman National Historical Park
Pullman was the country’s first planned industrial town, on Chicago’s South Side. It’s a quiet history stop, and kids can earn a Junior Ranger badge. Are you looking for more national park sites? See our guide to Illinois national parks.
Lincoln’s Springfield
Springfield has Lincoln’s home, law office, and tomb, plus the best presidential museum in the country. It’s three hours south and on our list. Want more NPS sites nearby? Check out our Illinois national parks guide.
Starved Rock State Park
Starved Rock has sandstone canyons and waterfalls ninety minutes southwest of the city. Go after a spring rain or when the falls freeze.
Galena
Galena is a hillside town of brick storefronts just across the river from Dubuque. We were close on our Iowa trip but didn’t make it over.
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Find your next adventure in Illinois
Tell us what you’re planning and we’ll match it up with some great trip ideas.
How to Spend a Weekend in Chicago with Kids
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Sunday Brunch at American Girl Chicago
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Routes
Three Illinois road trip itineraries
It’s one state and three very different trips. Choose a long weekend in Chicago, the Lincoln trail south, or the river towns on the western edge. See all the best stops on a map.
Home base
Downtown
Fly into ORD and take the Blue Line in. We stayed at the Radisson Blu Aqua right in the middle of things. Our weekend guide has the order that worked for us.
Then head to
Michigan Avenue
Have brunch at American Girl, then head to 360 Chicago across the street. Walk the Magnificent Mile to the Water Tower.
Add on
The museum campus
The Field Museum and the Shedd sit side by side on the lake. Do one a day. Our CityPASS definitely paid for itself on our trip.
Start
Springfield
Drive three hours south of Chicago, or fly into SPI. See the Lincoln Home, the Presidential Museum, and the tomb at Oak Ridge Cemetery.
Then head to
New Salem
It’s twenty minutes northwest. This reconstructed frontier village is where Lincoln lived in his twenties, and there’s lots of room to run.
Finish
Cahokia Mounds
It’s ninety minutes south near Collinsville. Climb Monks Mound, then cross into St. Louis for the Arch.
Start
Galena
It’s three hours west of Chicago. See Main Street, ride the trolley, and visit Grant’s home. Dubuque and the Field of Dreams are across the river.
Then head to
Starved Rock
It’s two hours southeast. Hike to French Canyon and St. Louis Canyon, and stay at the lodge if you can.
Finish
Chicago
Drive ninety minutes back to the city for a final museum day.
When to go
Time your visits with the weather and the region
We’ve done Chicago over Labor Day and again in warmer months, and the lakefront in late summer is hard to beat. Chicago’s winter is a serious one. Late spring and early fall are the sweet spot, and winter is for museums and a very cold walk to the Bean.
Swipe the chart sideways to see the full year.
May – June
The lakefront comes alive, the beaches open, and the summer crowds haven’t fully arrived. Starved Rock’s waterfalls are running.
July – August
It’s warm, humid, and packed. Lake Michigan is finally swimmable, Navy Pier has fireworks twice a week, and every festival in the city happens now.
September – October
This is our pick. Labor Day weekend was our first Chicago trip and the weather was perfect for walking. You’ll see fall color along the river by mid-October.
November – April
It’s cold and gray. Go for the museums, the Christkindlmarket in December, and the skating ribbon in Maggie Daley Park. Springfield is quiet and cheap.
Where to stay
Pick a good base to start your Illinois adventure
Stay downtown and skip the car. Here’s where we’ve stayed and where we’d stay next.
City trips
Downtown Chicago
There are a ton of chain hotels downtown. Pick one and you can walk or rideshare to everything. The Loop, River North, and Streeterville are all full of points hotels, and weekend rates drop.
- Where we stayed for our weekend
- Streeterville for Navy Pier and the beach
- Skip the car. Parking is fifty dollars a night
Lincoln trips
Springfield
Springfield is a small capital with chain hotels downtown within walking distance of the Lincoln sites. It’s easy on points and easy on the budget.
- Downtown near the Presidential Museum
- Route 66 motels on the edge of town for fun
- Book ahead for the state fair in August
Outdoor trips
Starved Rock & Galena
Starved Rock Lodge is a CCC-era lodge inside the park and the reservation to get. Galena runs on inns and cabins, and fall weekends sell out early.
- Starved Rock Lodge for the trails
- Galena’s Main Street inns
- Eagle Ridge Resort for a pool and golf
Good to know
Questions families ask us about Illinois
No, you don’t. We took the Blue Line from O’Hare straight to downtown and walked or took the train the rest of the weekend. Parking downtown runs fifty dollars a night, so a car is a cost with no benefit. Rent one only on the day you leave the city.
Pick the Shedd Aquarium. It’s the most engaging for toddlers and preschoolers, and the beluga tank alone is worth the ticket. The Field Museum is better for kids old enough to care about Sue and the mummies, and that was the hit for ours. Museum of Science and Industry is the pick for older kids. We used a CityPASS and it covered most of what we did.
Online, as early as the calendar allows, and weekends go first. We did Sunday brunch and stopped by the store the night before so our daughter could pick out a doll to bring. It was a splurge, but a lot of fun. Dolls get their own chair. Here’s how it went.
The tourist areas are as safe as any big city. Stay on the well-traveled streets downtown and along the lakefront, use the trains during the day, and use the same judgment you’d use anywhere.
A long weekend covers the highlights. Our first trip ran Friday to Monday over Labor Day. We did American Girl, both towers, two museums, and deep dish without feeling rushed. A full week lets you add the Shedd, the architecture cruise, Navy Pier, and a beach day.
Map
Essential Illinois, mapped
Keep exploring
Where to go next
Iowa with Kids
Dubuque is across the river from Galena. It’s a great Labor Day road trip.
