Family & Kid-Friendly Getaways from Chicago: # Trips for All Ages to Enjoy

Getaways are a great way for families to share moments and make memories. When you're ready for your family vacation from Chicago, whether you've got a single day to spare or are ready for a weekend-long adventure, opportunities for unique experiences and meaningful memories abound.

• Best for families with kids of all ages - Lake Geneva, Wisconsin
• Best for nature-loving families wanting to escape the city bustle - Starved Rock State Park, Utica, Illinois
• Best for sand lovers and small-town explorers - Indiana Dunes, Indiana
• Best for city-loving families with tweens and teens - Milwaukee, Wisconsin

• Best for outdoor enthusiasts and alone-time seekers - Door County, Wisconsin
• Best for families that love the beach and the arts - Saugatuck and Holland, Michigan
• Best for families who want to be near the Dells but also enjoy lake life - Castle Rock Lake, Wisconsin

• Best for city-exploring families with kids of all ages - St. Louis, Missouri
• Best for mountain-loving families and artsy folk - Asheville, North Carolina
• Best for big country fun - Austin, Texas

The best kid-friendly getaways from Chicago are getaway spots close enough to be a two-hour road trip, so you don't hear "are we there yet?" too many times. Whether you barely cross the Illinois border or venture into another state, having limited time for an adventure won't limit the fun things the family will experience and the memories you'll make in these destinations.

• ‌Perfect for‌: Families with kids of all ages
• ‌Highlights of Lake Geneva:‌
  • Beautiful beaches and full-service resorts
  • Outdoor activities and waterparks
  • Historic downtown and lakeshore dining

Driving to Lake Geneva from Chicago is an easy hour and a half, whichever way you go. Take the Dan Ryan (I-90W/I-94W) to the Tri-State Tollway (I-294N), then to WI-50/75th Street. You can also take the Eisenhower (I-290) to Route 12 and take that right into Lake Geneva.

Geneva Lake has plenty of family-friendly activities on or near the lake. Take in the sun at Big Foot Beach State Park in the summer, or enjoy snowshoeing and cross-country skiing in the winter.

Take an all-ages Ice Cream Social Cruise on Lake Geneva Cruise Lines, book a planetarium tour of the Yerkes Observatory, and spend a day at Timber Ridge Lodge & Waterpark enjoying the 50,000-square foot water park and fun-filled arcade. If the kids love to bring home souvenirs for friends, hit the fun and quirky shops in picturesque downtown Lake Geneva.

Lake Geneva has accommodations to fit every family. Camp at Big Foot Beach State Park or book your family hideaway steps from downtown, like this rental unit that is "All About the Zen."

Want something a bit more all-inclusive? I love Grand Geneva Resort & Spa because it has everything a family needs for fun and all a parent can ask to relax, recharge and indulge. An indoor waterpark, outdoor swimming pools, casual and upscale dining, a private 20-acre lake, and guest rooms with all the amenities. The resort welcomes pups up to 25 pounds in its select pet-friendly rooms.

• ‌Perfect for:‌ Nature-loving families wanting to escape the city bustle.
• ‌Highlights of Utica‌:
  • Natural waterfalls and canyons
  • Hiking trails and water activities
  • History to explore

It takes about one and a half hours by car from Chicago to Utica. Take I-90 E to I-55 S. Exit onto I-80 W toward Iowa and follow it for about 45 miles until you see signs for IL-178 toward Utica.

Starved Rock State Park takes center stage on this fun family getaway. The park has 13 miles of trails and 18 canyons to explore. Whatever season you visit, you will be in awe of the park's natural beauty. Stop at the Starved Rock Visitor Center to learn about the history of this National Historic Landmark.

The Starved Rock Lodge and Convention Center has many family-friendly fun, such as trolley tours, waterfowl cruises, live music, and nature-centered activities. Just miles south of Utica, you can explore beautiful Matthiessen State Park, too.

When the kids are ready to take off their hiking shoes and put on their swimsuits, head over to Grand Bear Falls Waterpark for 24,000 square feet of splashing and fun, an arcade, and a mini-golf.

A 20-minute drive east will get you to Ottawa, a historic downtown with boutiques, eateries, and events. It's a great place to spend a few hours or grab lunch — and the grown-ups will love Jeremiah Joe's Coffee.

If you're looking for a hotel with a historic and nature-filled vibe, Starved Rock Lodge is a bustling log-cabin conference center right in the park with everything from modern hotel rooms to charming cabins.

This Airbnb Fun Escape rental in Ottawa has all the fun and games (literally) that a family with young kids could want. The entertainment-focused living room and kitchenette are about as kid-friendly as it gets, and there is a private patio to relax in after busy, fun-filled days.

• ‌Perfect for:‌ Sand lovers and small-town explorers
• ‌Highlights of Indiana Dunes‌:
  • Dunes and beaches
  • Outdoor adventures
  • Charming nearby main streets and nearby Valparaiso

A short 32-mile drive from Chicago, Indiana Dunes can be reached in under an hour via I-90 E to US-12 E/ Dunes Highway. Get off at N County Line Road and look for signs to lead you to the dunes.

With 15,000 acres of sand dunes, woodlands, prairies, and marsh in Indiana Dunes State Park, families who love to hike, bike, bird watch, and camp will have no shortage of outdoor activities to run off to.

There are also 15 miles of sparkling, sandy beaches to explore. West Beach is great for families and has year-round restrooms, lifeguards, and reservable picnic shelters.

The nearby towns of Chesterton and Valparaiso are fantastic for small-town exploration. Chesterton's European Market's food, art, and entertainment make you feel far from the Midwest. Stop in Valparaiso for quaint shops, the Central Park Plaza farmers' market, and the lovely garden walks of the Gabis Arboretum.

If you've got fans of the railroad in the family, stay at Riley's Railhouse in Chesterton. The rail-car guest rooms are in the Old Freight Station, and the caboose is my family's favorite! Be prepared to hear some real-life train sounds during your stay.

The kids will love exploring the 44 gorgeous acres of this Barn rental called The Good Farm in nearby Valparaiso. It's about a 30-minute drive from the Dunes, but this family getaway spot is hard to beat.

• ‌Perfect for‌: City-loving families with tweens and teens
• ‌Highlights of Milwaukee:‌
  • Milwaukee Public Museum and County Zoo
  • Historic Third Ward
  • Beaches

Not all families are looking to escape city life on their getaway. With old-fashioned charm and glittering modernity, Milwaukee is Chicago's baby sister city, perched prettily on Lake Michigan — and it offers lots of family fun, especially for older kids.

Kids of all ages will love the Milwaukee County Zoo and Milwaukee Public Museum. American Family Field is a great place to catch the Cubs playing the Brewers if you're a baseball family.

The Milwaukee Riverwalk winds through the city, making it an ideal way to explore its notable neighborhoods, including the artsy Historic Third Ward, the downtown theater district, and Brewers Hill.

If your family loves art and the theater, you can't go wrong in Milwaukee, from the gorgeous Milwaukee Art Museum to the thriving theater district with Marcus Center and Milwaukee Rep.

To get to Milwaukee, you can kick back and take Amtrak aboard the 90-minute Hiawatha service, which runs multiple times daily between Chicago and Milwaukee. To drive, take the Edens Expressway (I-94W) to I-43 N, then take I-794 E toward Lakefront.

You can find a short-term, family-friendly rental in any neighborhood of the city, ranging from a condo downtown to a bright and cozy home in nearby Bayview.

If you're a hotel-loving family who loves to be right in the middle of the action, The Pfister Hotel in the heart of Milwaukee puts you within walking distance of most major attractions and has a swimming pool with a view of the city.

When you've got a little extra time and can make your family weekend getaways from Chicago last longer, these destinations welcome you within a five-hour drive.

• ‌Perfect for:‌ Outdoor enthusiasts and alone-time seekers
• ‌Highlights of Door County:‌
  • Endless outdoor activities
  • Skyway drive-in
  • Waterparks

Take I-94N to I-294N and head to I-43N. From there, take WI-54E/WI-57N to County Q to head into town. The trip takes about four and a half hours. Cedarburg or Elkhart Lake are halfway points if you need to stop and stretch your legs in a quaint little town.

The trails, beaches, cliffs, waterfalls, and caves make Door County an ideal place for a family to spend time together in the great outdoors, kayaking, paddling, hiking, zip lining, boating, or canoeing.

For those not-so-actively adventurous days, there are plenty of ways to explore. Jump on the Door County trolley for a tour, take in a show under the stars at the Skyway Drive-In Theatre, grab a frozen custard at Not Licked Yet in Fish Creek, or hit the amusement park and arcade at Egg Harbor Fun Park.

Door County has no shortage of charming cabins and breakfasts. If your family loves to kayak, I recommend this Door County Cottage rental in Sturgeon Bay. It's the perfect mix of woods and beach, the host welcomes dogs, and you have access to the "Family Fun Shed."

Some families prefer a resort experience, so I highly recommend The Edgewater Resort. It's quaint and luxurious at the same time and offers amenities and adventure.

• ‌Perfect for:‌ Families that love the beach and the arts
• ‌Highlights of Saugatuck and Holland:‌
  • Great Lake Michigan beaches
  • Bustling downtowns
  • Natural beauty and outdoor activities

The drive from Chicago to Saugatuck is roughly 2 hours and 15 minutes via the Dan Ryan (I-94E). Take I-94E to the Indiana Toll Road and then to I-196N, following the signs to Holland/Grand Rapids. Head to the Blue Star Highway and drive into town via Lake Street. New Buffalo or St. Joseph is about the halfway point if you need a little breather. Holland is just a 20-minute drive north from there.

Saugatuck is called Lake Michigan's "Art Coast" for a reason. And Holland is like its sister city just 20 miles northeast, full of history and charm. Between the two small towns, there is something for every family member.

To get a fun look at the area's natural beauty, Saugatuck Dune Rides are a must. If you prefer a view from the water, take a ferry ride or a cruise on the Star of Saugatuck. Hit family-friendly Oval Beach for a day at the shore and then drift into town for something to eat at one of the many excellent Saugatuck-Douglas eateries.

On your day trip to Holland, visit Centennial Park, explore Windmill Island Gardens, and go back in time at Nelis' Dutch Village. Learn the history of this Dutch town at the Holland Museum.

The BeachWay Resort and Hotel in Saugatuck is a family paradise close to Oval Beach that offers suites, rooms, and even adorable stand-alone cottages.

There are also many great family rentals, like this Hansel and Gretel Cottage in downtown Saugatuck. Its fairy-tale feel is just steps away from the bustle of town.

If the family loves Holland enough to stay in town, check out this Lake Ridge Cottage rental near the beach and town center.

• ‌Perfect for:‌ Families who want to be near the Dells but also enjoy lake life
• ‌Highlights of Castle Rock Lake:‌
  • Buckhorn State Park
  • A half-hour drive to Wisconsin Dells
  • Wisconsin River activities

Chicago to Castle Rock Lake is about three and a half hours by car. Take I-90 W to County Rd HH, and look for signs to Castle Rock Lake.

Castle Rock Lake is a 26-mile lake on the Wisconsin River. Some nearby lake towns are Necedah, Dellwood, New Lisbon, and Mauston.

Visit Buckhorn State Park in Necedah to get a great lake view. Rent a pontoon, waterskis, or kayaks at Castle Rock Watersports in Mauston, and when you return to shore, snack on some cheese curds and fried pickles at Shipwreck Bay. Or satisfy your Windy City pizza craving at Kozy's Pizza on the way home.

The Dirty Turtle is a fantastic beach hangout for grown-ups with a sandy little playground for the kids.

When you feel like taking a break from lake life, take a day trip to Wisconsin Dells to enjoy a day in the waterpark capital of the world.

We've stayed at cabins, and a condo rental during our trips to Castle Rock, and both were great for the whole family. This custom-built log cabin rental in Friendship is about 15 minutes from the eastern shore of Castle Rock Lake.

This condo in Arkdale has lakefront views, outdoor pools, and an onsite tiki bar and golf course.

When you find more time to explore, head to one of these destinations for the best family getaways within reach by a two-hour flight.

• ‌Perfect for:‌ City-exploring families with kids of all ages
• ‌Highlights of St. Louis:‌
  • Family-friendly cultural activities
  • Indoor and outdoor experiences for all ages
  • Nature and wildlife

St. Louis, poised on the banks of the Mississippi River, offers shareable experiences for the whole family. The artist-built, truly unique City Museum is a must-visit destination for all ages. The St. Louis Zoo, the Turtle Playground, Forest Park, Meramec Caverns, and Missouri Botanical Garden are just a handful of reasons why it's great to have a few days to take it all in.

You can't visit St. Louis without visiting the Gateway Arch Visitor Center and the Museum. Make sure the family takes the tram ride to the top of the arch. And if they like that, the roller coasters of Six Flags St. Louis are just 30 minutes away in nearby Eureka.

The Hill neighborhood in St. Louis is a quaint area originally settled by Italian immigrants, and it retains the feel of a "little Italy." Shop the markets, grab some great food, and play bocce ball at Milo's Bocce Garden.

You can drive to St. Louis in a little over 4 hours by taking I-55 S to I-64 W. From there, look for signs to St. Louis via Stadium/9th Street. Flying to St. Louis from Chicago is about 1 hour and 15 minutes nonstop.

This amenity-filled, two-bedroom rental is near the St. Louis Zoo and has enough space and amenities for the whole family.

The Cheshire is a family-friendly hotel with a bit of luxury, right in the middle of everything.

• ‌Perfect for‌: Mountain-loving families and artsy folk
• ‌Highlights of Asheville:‌
  • River arts district
  • Waterfalls and mountains
  • Downtown Asheville

When you bring your family to Asheville, you are giving them the experience of immense beauty, from the breathtaking waterfalls of Gorges State Park to the foggy majesty of the Great Smoky Mountains and the half-million-acre Pisgah National Forest.

Stop by The Adventure Center of Asheville for zip lining and other treetop adventures. If you have littles, the Botanical Gardens at Asheville have safe, family-oriented trails of varying lengths. And, of course, there is no shortage of natural hiking trails for older kids and grown-ups. Take a short 1-hour drive to the Great Smoky Mountains National Park for an awe-inspiring road trip.

There are plenty of great kid-oriented sites in Asheville, like the Asheville Museum of Science and the Hands-on! Children's Museum. For a day steeped in history, visit the Biltmore Estate and take part in some family-friendly Biltmore activities.

Getting a two-hour nonstop flight from Chicago to Asheville Airport (AVL) is easy, which lands you 15 miles outside the Asheville Historic District. Grab a cab or rideshare, and you'll be downtown within 20 minutes.

We recommend the Omni Grove Park Inn if you want to treat the whole family. The kids love the pool and the mountains, and I love the location, the service, and the sunsets. It's on the pricy side, but if you are staying a couple of nights, it's a gorgeous splurge.

For something right downtown, this luxury corner unit condo rental is a perfect spot walkable to downtown, with plenty of space for everyone and great views.

• ‌Perfect for:‌ Big country fun
• ‌Highlights of Austin:‌
  • Texas Capitol
  • Lake Travis
  • Downtown Austin

Take a dip in the heart of the city. Deep Eddy Municipal Pool is the oldest swimming pool in Texas and is filled with the cold springs from the river. Barton Springs Pool is a three-acre swimming hole fed from underground springs. Stop by Austin Rowing Club to rent a kayak or paddleboard if you're traveling with older kids.

The Texas State Capitol is a great place to visit as a historic site and for the beautiful view of downtown from the steps. From the capital, the highly interactive Austin Aquarium is about 15 minutes north, or you can head about 20 minutes west to visit the Austin Zoo.

For outdoor lake fun for the whole family, head to Lake Travis on the Colorado River, about 20 minutes northwest of downtown. Enjoy a lakeshore park, rent a boat, or take a zipline to enjoy its 64-mile-long beauty.

Lastly, if the rodeo is in town, don't miss it. Check out Rodeo Austin and the Visit Austin website to see what's on the calendar. If your family loves horseback riding, check into Texas Trail Rides.

For the grown-ups, Fredricksburg is about 78 miles outside of Austin, with some of the best wineries you'll find in the country.

Nonstop flights from Chicago to Austin-Bergstrom International Airport are easy to find and take less than three hours. From the airport, downtown Austin is a quick 15-minute drive.

We are fortunate enough to stay with family when we visit Austin. For a family-friendly stay with plenty of lake life and pool time, we suggest the Lakeway Resort & Spa on Lake Travis.

For the experience of downtown Austin, look for a rental with a great view of the city, like this one.

No matter the amount of time you have for your time away together, there are options for family friendly getaways from Chicago that will fit your schedule and lead you on a path to shared adventure . Even the shortest trips will have long-lasting impact on your family memories.