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My. Olympus in Wisconsin Dells
Photograph: Courtesy Wisconsin Dells Visitor & Convention BureauMy. Olympus in Wisconsin Dells

The best family weekend getaways from Chicago

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

Written by
Samantha Lande
Laura Rote
Allison Yates

Chicago boasts plenty of kid-friendly activities, but if you're planning a family vacation out of town, there are plenty of approachable, fun and memorable destinations close by for a weekend away. Cities, state parks, and lakes across the region are full of hiking for all ages and engaging, hands-on ways to learn about history, ecology and wildlife. Along the way, find quirky shops and hidden gems, kid-friendly restaurants with decadent desserts and recreational activities that kids of all ages will enjoy. From the wacky and weird the to active and relaxing, here are the best family weekend getaways from Chicago (all within four hours of the city).

Family weekend getaways from Chicago

Wisconsin Dells, WI
Photograph: Nick Collura

1. Wisconsin Dells, WI

Driving time from Chicago: Three hours

The waterpark capital of the world—what's not to love? It doesn't matter if the weather is sunny or rainy, though, because this Wisconsin town offers both indoor and outdoor parks. Mt. Olympus is one of the biggest and most popular, with both water and theme park attractions (and rides for the really little ones as well). Those looking to do something a little different can visit MagiQuest in the Great Wolf Lodge to participate in a live-action role-playing game. If the litte ones come up for air long enough to eat, head to Buffalo Phil's, where kids get their food delivered on a train before spending some coinage in a giant arcade. Paul Bunyan's is a fun, themed spot for an all-you-can-eat breakfast.

If you're looking for animals, look no farther than Timbavati Wildlife Park for behind-the-scenes tours with exotic animals. Or let the kids feed gentle deer at Wisconsin Deer Park.

Hamilton County, IN
Photograph: Hamilton County Tourism

2. Hamilton County, IN

Driving time from Chicago: Three hours

Take a trip back in time at the Conner Prairie Interactive History Park and explore 1836 Prairietown, see a Civil War reenactment or stroll along the nature walk. There’s also a large Swiss Family Robinson–esque tree house called Treetop Outpost for the whole family to enjoy. Then, of course, there's Conner Prairie’s tethered helium balloon, which elevates guests 377 feet above the prairie for unbeatable views over Indiana.

Nearby, you can take to the more than 300 miles of trails in the county, including paved paths that lead to shopping, dining and sightseeing. Bring your bike or rent one during your stay.

Lake Geneva, WI

3. Lake Geneva, WI

Driving time from Chicago: One and a half hours

At a sprawling resort like the Grand Geneva, you can count on plenty of activities to keep the family busy. Explore the Dan Patch Stables, where the kids can go on pony rides and feed the animals in the free petting zoo. Waterpark lovers will clamor for Moose Mountain Falls, a 50,000-square-foot waterpark.

If you're looking for a full day of adventure, head to nearby Kenosha for America's Action Territory Fun Park, where you'll find everything from bumper boats and cars to laser tag and batting cages. For dinner, check out Popeye's (not the chain with an amazing fried chicken sandwich): It's super family-friendly with great views of the water and a large menu.

Door County, WI
Photograph: Shutterstock

4. Door County, WI

Driving time from Chicago: Four hours

A longtime favorite of Chicagoans seeking a bit of R&R, Door County has more to do than your family will be able to fit into just one weekend. Kids will make some amazing memories with the host of experiential activities, like feeding a baby goat at The Farm, making their own crafts at Hands On or ziplining, gem mining or go-karting at Egg Harbor Fun Park. More active families will love exploring the stunning Cave Point County Park--you can even get kayak cave tours or stand-up paddleboards through Gravity Trails

The region isn't short on kid-friendly restaurants either -- go for highly cutomizable wood-fired pizzas at Wild Tomato or watch goats graze on the roof at Al Johnson's Swedish Restaurant and Butik. And don't forget to stop at Door County Creamery for some indulgent gelato. 

Indianapolis, IN

5. Indianapolis, IN

Driving time from Chicago: Three hours

Indianapolis has enough indoor and outdoor activities for a fun-filled weekend. Head to the The Children's Museum of Indianapolis for top-notch exhibits like the planetarium and the recently-updated Dinosphere, where kids can dig for dinosaur bones. It also has a great play area for toddlers. For some fresh air, walk or bike along the Monon Trail, a 10.5-mile path that runs through most of Indy. Stop in the Broad Ripple neighborhood to browse some shops and grab a scoop of ice cream at Brics.

Rest your weary heads at the Crowne Plaza Downtown Indianapolis Union Station, and be sure to call ahead to check for family packages that may include lodging plus tickets to attractions like the Children's Museum and Indianapolis Zoo.

Holland, MI
Photograph: Dan Irving

6. Holland, MI

Driving time from Chicago: Two and a half hours

Since the mid-19th century, the small city of Holland has been home to wooden shoes and tulips. Whether you're there in time for the Tulip Time Festival in May or want to visit the Windmill Island Gardens, the family will have a blast. Check out a working 250-year-old Dutch windmill—”De Zwaan,”—or stroll 36 acres of pristine lawns; bring your picnic blanket and a camera for a vibrant family photo op.

During the day, catch a tour of the 125-foot windmill from a guide in traditional plaid Dutch garb. Need even more flowers? See more than 5 million in bloom in April and May at Veldheer Tulip Gardens. To take home a piece of Holland, though, you must not miss De Klomp Wooden Shoe and Delft Factory, where you can also enjoy a free tour of the famous, centuries-old pottery maker from the Netherlands. Once you've worked up an appetite, take the kids out for an authentic Dutch dessert like sugar bread from deBoer Bakkerij.

If you need to burn off some energy, a 20-minute drive takes you to Saugatuck Dunes State Park. Surrounded by 300 acres of nature and dunes that rise up to more than 200 feet tall, you won’t have a care in the world running and playing along this long, sandy shore.

Peoria, IL
Photograph: Mark Ballogg, Courtesy Discover Peoria

7. Peoria, IL

Driving time from Chicago: Two and a half hours

There’s plenty of family-friendly history, recreation and adventure in Illinois’s oldest European settlement. Enjoy the scenic views and watch the barges go by along the RiverFront District before making a stop at the The Peoria Riverfront Museum to immerse yourself in space shuttle launches, solar systems and eclipses in the domed planetarium then fill up on smoked meats and burgers at The Blue Duck Barbecue Tavern, housed in a repurposed train depot utilized from 1899 until 1978. Sleep close to the activities at the Mark Twain Hotel, a quaint and understated 111-room accommodation 10 minutes walking from the RiverFront.

You’ll also find lots of greenery and wildlife to experience, even within city limits. Spend time at the 60 square miles of parks—the oldest park district in Illinois. Wander around the 5-acre Luthy Botanical Garden for year-round floral beauty or hike through seven miles of trails in Forest Park.

Harbor Country, MI
Photograph: Laura Rote

8. Harbor Country, MI

Driving time from Chicago: One hour and 15 minutes

With a population of less than 2,000 permanent residents, the small lakefront city of New Buffalo is charming for all ages. If traveling by train, Amtrak will drop you off near The Harbor Grand, where a stay feels like home but cozier, with an in-room fireplace and harbor view (or glimpse of frozen lake). During warm months, you can hop on one of the hotel's bikes for a quick ride around town. And kids will always get a kick out of the nearby Hesston Steam Museum and Captain Mike's Fun Park.

For lunch, Redamak’s is the popular burger joint in the area, filled with fun activities for kids, including a mini firetruck. And what would a visit to a beach town be without ice cream? Don’t miss funky Oink's Dutch Treat Ice Cream & Yogurt Shop.

For dinner, visit the hotel’s Terrace Room for a comforting Italian dish like spaghetti and meatballs (described as Grandma’s family recipe with sweet marinara) that everyone will love. Or pop over to Bentwood Tavern for wood-fired pizza.

Ottawa, IL
Photograph: Kathy Casstevens/Starved Rock Lodge

9. Ottawa, IL

Driving time from Chicago: One and a half hours

In just an hour and a half, you'll be transported to a beautiful setting filled with both water and land activities to keep your family entertained. Hike at nearby Starved Rock State Park or Buffalo Rock State Park; bike along the I & M canal trail that runs for more than 60 miles; take a dip in the on-site pool or build sandcastles and pack a picnic at the aptly named Picnic Grove. You can also rent a variety of boats, kayaks, water skis and canoes at a nearby private beach.

Renting a cottage is the way to go, and you can find a lovely place to rest your head at Heritage Harbor's Cottage at Heron's Landings.

10. Battle Creek, MI

Driving time from Chicago: Two and a half hours

There are no picturesque tree-lined streets or Michelin-star restaurants in the manufacturing hub nicknamed “Cereal City,” but it’s full of wacky family adventures. The home of Kellogg’s and Post Consumer Brands honors its origins with an annual CerealFest each June. If you miss it, venerate America’s favorite breakfast any time of year with a visit to The Calhoun County Visitors Bureau’s "Cereal History" exhibit to journey through the history, manufacturing, and culture significance of Battle Creek native John Harvey Kellogg’s invention.

After some cereal nostalgia, meet rescued gators at the Critchlow Alligator Sanctuary twenty minutes south of Battle Creek. There are more than 180 alligators on site, including the 11-foot "Godzilla."( Don’t worry—staff only let the kids touch the small ones.)

Grab dinner a turkey buffet dinner at Cornwell’s Turkeyville USA and then stay for one of the venue’s rotating musicals or theatre performances. For those who prefer more traditional animal encounters, you can glimpse lions, zebras and giraffes at Binder Park Zoo in Battle Creek.

Back in Battle Creek, as the sun sets over Goguac Lake, you can pretend you’re miles away from Southwestern Michigan at the ostentatious McMansion Paradise Island the Fantasy of the Nouveau Riche. Filled with regionally inappropriate nautical decor, this rental on the lake’s Clark Island sleeps 12, is only accessible by boat and features big windows that offer lake views.

Northern Indiana
Photograph: Courtesy Visit South Bend Mishawaka

11. Northern Indiana

Driving time from Chicago: One hour and 40 minutes

With the charming university town South Bend as your home base, spend time exploring Northern Indiana’s outdoor expanses and Amish culture. Start with a visit to St. Patrick’s County Park, a 398-acre preserve with activities for any season. The park features year round bird watching opportunities and hiking along the numerous trails of varying lengths, canoeing and kayaking along St. Joseph River in the summer and cross country skiing in the winter.

During summer visits, make time to browse outdoor markets running May through September. The South Bend Farmers Market and the Mishawaka Farmers Market are both go-to spots for sampling local produce and artisanal cheeses and meats.

You can easily spend an entire day at Shipshewana Auction & Flea Market—the largest in the Midwest—located an hour drive east from South Bend. The size of more than 30 football fields, you’ll find antiques and vintage furniture, decor, apparel, food stalls, and even plants. On your way back to South Bend, make a stop in Middlebury, a town of around 3,500 with a strong Amish presence. Visit the original Rise ‘n Roll Bakery and Deli and grab a box of the notoriously addictive cinnamon caramel doughnuts.

Walworth County, WI
Photograph: Brad & Jen Photography

12. Walworth County, WI

Driving time from Chicago: One hour and 40 minutes

If you’re looking for an off-the-beaten track destination to unplug and reconnect with nature, the Walworth County lakes within thirty five minutes of Lake Geneva are a no-brainer. At Delavan Lake, Whitewater Lake, Rice Lake, Lauderdale Lakes (comprised of three interconnected lakes) and nearby Lake Wandawega to the south and Pleasant Lake to the north, visitors can canoe, kayak, fish, swim and hike. Head south to the 12-mile White River Trail for hiking, biking and horseback riding.

Whitewater Lake’s Scenic Ridge Campground offers wooded or grassy campsites along the water, access to volleyball nets, horseshoe pits, hiking trails and inflatable pillows—plus, and an extensive calendar of sports, entertainment and activities for folks of all ages.

Brown County, IN
Photograph: Courtesy Brown County Convention & Visitors Bureau

13. Brown County, IN

Driving time from Chicago: Four hours

Brown County State Park is famous for its vibrant fall colors, but this nature oasis 30 minutes northeast of Bloomington is fun during any time of the year. Indiana’s largest state park often referred to as the “Little Smokies” has 11 hiking and 14 mountain biking trails of varying lengths and difficulty levels—plus, 20 miles of roads for when your legs get tired—you can mix and match for your desired adventure, whether it's to see stunning views of rolling tree-covered hills and waterfalls or to feel immersed in the backcountry. If you need to rent two-wheeled transport, stop by Q’s Bikes.

There are plenty of campsites around the park, but for indoor stays head just outside the park boundaries to Nashville, a small town full of mom-and-pop craft stores, fudge shops, ice cream and restaurants with live entertainment. Cornerstone Inn has a campus of 41 affordable accommodations around town and a cabin in the woods. The delicious pizzas and craft beer at Big Woods are much needed fuel after an active day—and don’t skip the sizzling skillet cookie topped with ice cream.

Galena, IL
Photograph: Jamie Loso

14. Galena, IL

Driving time from Chicago: Three hours


Words people use regularly to describe Galena include “quaint,” “charming” and “historic,” but none of those have to also mean “boring.” One of the best all-ages options for more active families is the Chestnut Mountain Resort, a 100-room lodge featuring skiing and snowboarding in the winter and ziplining and a 2,050-foot alpine slide in the summer. 


If you don’t want to go the resort route, there’s still plenty to do in the great outdoors with the whole family, from kayaking or canoeing down the Galena River with a rented vessel from Nuts Outdoors to a scenic trail ride with the Shenandoah Riding Center to strawberry picking at Terrapin Orchards. For a fun, family-friendly evening activity, catch some thrilling illusions at the P.T. Murphy Magic Theater or get your nostalgia on with a drive-in movie at the Midway Drive-In in nearby Sterling. And if you’re browsing through downtown Galena, don’t forget a stop for some sweets at Galena Kandy Kitchen


15. Ann Arbor, MI

Driving time from Chicago: Four hours

There are plenty of reasons to take a family road trip to Ann Arbor, even when it isn’t Michigan football or basketball season. Kids can spend hours at the interactive Hands-On Museum or the Leslie Science and Nature Center, where they can run around the Nature Playspace and get up close with birds of prey in the raptor enclosure, or snakes and frogs in the recently-reopened Critter House. The whole family will find something to love exploring the shops and restaurants on colorful Main Street—the little ones will be particularly drawn to the nostalgic soda and sweet shop Rocket Fizz and the countless shelves of books, comics, toys and games at Vault of Midnight.

As for going out to eat with your whole crew, even the breweries here cater to craft beer enthusiasts with kiddos—Blue Tractor BBQ & Brewery and Jolly Pumpkin offer award-winning brews and hearty, creative food for the parents; with solid kids menu options and crowd-pleasing desserts. Speaking of dessert, a trip to Zingerman’s Deli for their decadent brownies is also a must.

Family-friendly day trips

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