Family weekend getaways from Chicago
3 hrs by car
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 (1701 Wisconsin Dells Pkwy) 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 (1401 Great Wolf Dr) to particpate in a live-action role-playing game. If the kids come up for air long enough to eat, head to Buffalo Phil's (150 Gasser Rd), where kids get their food delivered on a train. The restaurant is also attached to a giant arcade. Paul Bunyan's (411 State Hwy 13 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 (2220 Wisconsin Dells Pkwy) for behind-the-scenes tours with exotic animals. Or let the kids feed gentle deer at Wisconsin Deer Park (2183 Wisconsin Dells Pkwy).
Take a trip back in time at Conner Prairie Interactive History Park (13400 Allisonville Rd, Fishers, IN) and explore 1836 Prairietown, see a Civil War re-enactment and stroll along the nature walk. Even more recently, the large Swiss Family Robinson–esque tree house called Treetop Outpost opened at Conner Prairie for the whole family to enjoy. Then, of course, there's Conner Prairie’s tethered helium balloon, which elevates guests 350 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 trails that lead to shopping, dining and sightseeing. Bring your bike or rent one during your stay.
90 mins by car
At a sprawling resort like the Grand Geneva (7036 Grand Geneva Way), 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. For a fun family outing, play mini-golf at Paradise Golf Park.
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 (811 Wrigley Dr): It's super family-friendly with great views of the water and a large menu.
3 hrs by car
Indianapolis has enough indoor and outdoor activities for a fun-filled weekend. Head to the Children's Museum (3000 N Meridian St) for top-notch exhibits like the planetarium and 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 (901 E 64th St).
Rest your weary heads at the Crowne Plaza Downtown Indianapolis Union Station (123 W Louisiana St), and be sure to call ahead to check for family packages that may include lodging plus tickets to attractions like the Indianapolis Zoo.
2 hrs, 30 mins by car
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 (1 Lincoln Ave), 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 (12755 Quincy St). To take home a piece of Holland, though, you must not miss De Klomp Wooden Shoe and Delft Factory (12755 Quincy St), 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 (360 Douglas Ave).
If you need to burn off some energy, a 20-minute drive takes you to Saugatuck Dunes State Park (6575 138th Ave). 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.
1 hr, 15 mins by car or Amtrak
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 (111 W Water St), 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 (call for hours) and Captain Mike's Fun Park (10975 Red Arrow Hwy, Bridgman, MI).
For lunch, Redamak’s (616 E Buffalo St) 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 (227 W Buffalo St).
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 (600 W Water St, 269-469-1699) for wood-fired pizza.
90 mins by car
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 (2668 East 873 Road, Oglesby, IL) 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 (1970 N 2753rd Rd).
Family-friendly day trips
With new states to explore just a short drive away, Chicago is perfectly situated for a quick jaunt to regional wonders with the little ones in tow.