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Family Road Trips From Chicago

Where To Stay In Indianapolis With Kids


Book your stay at theCourtyard Indianapolis Downtown or, book theResidence Inn Indianapolis Downtown on the Canalwith Travelocity today!

When location matters, stay at Indianapolis Courtyard Indianapolis Downtown and you will be within walking distance of restaurants, have access to the sky bridge to the Indiana Convention Center. Plus, its less than two miles from the Indianapolis Zoo. Another hotel with a pretty location along the downtown canal is the Residence Inn Indianapolis Downtown on the Canal.

Ski The Holy Trinity Of Fresh Powder In The Michigan Upper Peninsula

Distance from Chicago: 398 miles northwest, six-hour driveWhy it made our list:It doesnt get any better for skiing in the Midwest than a trip to Michigans placid, snow-covered Upper Peninsula, where the resorts of Indianhead, Big Powderhorn, and Blackjack offer a welcome respite from the shitty ice trails near Chicago.Bonus points: All three resorts are good but if you have to pick one, go with Indianhead. It has the highest vertical drop, 15 pristine expert runs, and a surprisingly happening late-night scene with not one, but two live music venues on the mountain.

Best Road Trips From Chicago

If you live in Chicago and want to get out of the city or you’re just visiting the Windy City and want to make a few drives out, there is a lot of road trip options.

Sitting right on Lake Michigan with the Great Lakes and a number of surrounding states within easy reach, there is every reason to get in the car and explore.

Featuring city breaks, small coastal harbor towns, outstanding natural parks and the occasional wineries and breweries, here are our 20 best road trips from Chicago ordered from closest to furthest away – make sure to read further down for more epic road trip itineraries!

1 hour from Chicago

Only an hour away from downtown Chicago, Indiana Dunes became the newest National Park in the United States in 2019.

You can easily visit on a short day road trip from Chicago, but if you want to explore the different trails and get away from it all, a weekend trip might work better despite being so close.

The dunes stretch along a 15-mile stretch of Lake Michigan and the National Park borders the State Park of the same name. The 3 tallest sand dunes are all in the State Park with the tallest, Mount Tom, standing at 192 ft.

There are a number of different trails that will take you up and down the dunes, past groups of trees that have been overcome by the sand, dune blowouts and pine forests.

With a lot of water activities on the lake, the parking lots can fill up quickly so make sure you get here in the morning to get a spot.

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Relax With A Trek Through Saugatuck Dunes State Park

Driving time from Chicago: 2 hoursDistance from Chicago: 140 miles

Located on the other side of Lake Michigan, Saugatuck Dunes State Park is an incredible destination for travelers looking to relax at the end of their road trip from Chicago. It comprises about 1,000 acres of land and features freshwater coastal dunes, with some more than 200 feet tall. This place is a hiker’s dream, but you can also enjoy the lakefront shoreline.

Niagara Falls And Niagara

10 Fun Family Activities in Chicago

8 hours 20 minutes from Chicago

Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience and one that’s different to any other trip you might take.

Head across the border to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Canada produces a significant proportion of the world’s Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested.

Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter.

How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination.

If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you’re heading across Rainbow International Bridge.

NOTL is also a really charming little town, and while you’re here you might like to take a horse-drawn carriage ride through its historic streets – a wonderfully atmospheric way to travel through the snow-covered streets.

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Best Road Trip Route From Chicago To Toronto

The best route option for your road trip from Chicago to Toronto will depend on the time you have put aside to reach your destination, and what you’d like to see along the way.

Both routes make for a fantastic journey, and take you past some great attractions, so read on to help decide which route to take.

Apple River Canyon State Park

Nature lovers looking for respite from city life will find it at Apple River Canyon State Park in the rolling hills of northwest Illinois. Inside the park, visitors can see the Apple River carving its way through a limestone canyon.

Anglers will appreciate early spring trout fishing along with summer sunfish and small-mouth bass fishing. Four picnic areas along the scenic river give visitors an opportunity to barbecue and make use of park grills, tables, and nearby restrooms. Hikers are advised that the five rugged trails crisscrossing the woods present potential hazards. Flora and fauna are abundant in the park.

8763 E. Canyon Road, Apple River, IL, Phone: 815-745-3302

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Toronto & Niagara Falls

Chicagoans rarely consider Toronto, Canada as a road trip option, but its only 8 hours away if traffic and border crossings cooperate. Add another 90 minutes to reach Niagara Falls, one of the great natural wonders of North America.

Chicago and Toronto are incredibly similar. They have nearly identical-sized populations . Both have great museums, outdoor adventures, cultural experiences, culinary delights, and vibrant nightlife.

A few things Toronto has that Chicago doesnt: The Hockey Hall of Fame, the CN Tower, and a chance to paddle in the Harbor Islands. For a silly tourist attraction, check out the Bata Shoe Museum.

On the way to Toronto, youll pass through the town of London, Ontario, Canada. This city has lots of interesting attractions and fun things to do, so check it out!

Awesome Road Trips From Chicago

Famous Illinois Route 66: A Road Trip from Chicago to Springfield

Keeping your introduction to road trips from Chicago short and simple, lets take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but its also a great starting point for some great Chicago road trips. The citys prime location acts as a portal to the Midwest from historical cities to sprawling state parks and urban-stress-relieving beer.

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Pop A Wheelie In The Snowmobile Capital Of The World In Eagle River Wisconsin

Distance from Chicago: 331 miles north, 3.5-hour driveWhy it made our list: Eagle River isnt just famous as the hometown of Charles Comiskey . Its also the self-declared world capital of snowmobiling with 500+ miles of groomed snowmobile trails and the World Snowmobile Headquarters . Rent one of these demonic winter beasts from The Toy Shop or blaze a guided tour trail with Decker Sno-Venture Tours.Bonus points: Eagle Water Resort is prime real estate for renting a quiet cabin on the peaceful chain of lakes and scanning the skies for bald eagles. It also has a snowmobile trail, duh.

Naperville Riverwalk And Downtown

For a slightly smaller town feel and to get kids out of the city, families can take a Metra ride or drive out to Naperville, Illinois. The Western Suburbs Riverwalk offers almost two miles of brick paths with fountains, bridges, and outdoor sculptures. Along the River Walk, visitors can rent paddleboats, paddleboards, or kayaks for a water adventure in the quarry. Downtown Naperville also has several family-friendly shops and restaurants including Andersons Bookshop and Sweet Home Gelato.

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Indiana Dunes National Lakeshore

Indiana Dunes National Lakeshore provides visitors with a 15-mile stretch of beach along Lake Michigans southern shore thats perfect for a beach day getaway. Fifty miles of diverse trails weave along the lakeshore where visitors can hike, bike, ride on horseback, snowshoe, cross-country ski, or bird watch.

Besides beaches, highlights include interpretive programs, ranger-led walking tours, the childrens outdoor Nature Play Zone at the Paul H. Douglas Center, four historical buildings from a 19th century homestead, and a 3500-square-foot modern pavilion. Every day trip should include a hike up West Beachs Succession Trail for an epic view of the Chicago skyline.

1100 N. Mineral Springs Road, Porter, IN, Phone: 219-395-1882

Illinois Great River Road

5 great family road trip destinations a day

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes.

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Day Trips From Chicago: Brookfield Zoo

Since 1934, the Brookfield Zoo has enthralled while simultaneously teaching more than 2 million visitors annually. The over 200-acre nature park houses over 2,000 animals and is equipped with a fully accredited arboretum.

As a world-renowned zoo, visitors can enjoy an eclectic array of wildlife highlighting various places around the globe Australia House and Habitat Africa are two shining examples of this. Visitors can do everything from watching dolphins in action to having hands-on experiences with red pandas, reindeer, and alpacas. In addition to animal encounters, attractions such as face painting, carousel rides, and motor safaris add to the fun.

8400 31st Street, Brookfield, IL, Phone: 708-668-8000

Free points of interest close to me: Natchez, Atlantic City, Carlisle

Best Family Weekend Getaways From Chicago

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For somebody living in Chicago, a weekend break outside of the city occasionally is a good idea. It is especially good if you take your family and kids along.

After all, there is no better stress buster than a weekend getaway with family. If you stay in the Windy City, a good weekend break from Chicago is very near.

Within drives of just an hour or three from the big city you can have a well-planned or a last-minute road trip.

Relax on the beach, go on a hike, a bike ride perhaps or do some shopping.

Some of these destinations are romantic getaways and some adventure destinations. These getaways are also good for romantic couples and elders. So be wise in choosing the right one for your family.

Elders may not prefer road trips as much as the younger ones in the family. You may want to keep the distance short if they are also part of the road trip.

Whatever is your choice, do get out of the house.

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Chicago To New York Road Trip

Although the idea of this 12 hour drive may feel daunting at first, with many historic and scenic stops to make along the way, this is one of the best road trips in the USA for families.

We suggest you allow yourself 10 days to complete the journey, including time spent in both Chicago and New York City to even touch on the highlights.

Discover Hidden Gems At Lansing Michigan

Chicago Road Trips That Are One Tank Away

If you’re taking the Northern Route between Chicago and Toronto, Michigan’s state capital Lansing is almost half way between the two. We don’t just recommend it for its convenient location though.

As well as a thriving downtown area where you can take your pick of places to eat after a day on the road, you could visit the Eli and Edyth Broad Art Museum which has an interesting collection in a contemporary building. Or if you’d rather spend time outdoors, the W J Beal Botanical Garden is the perfect place.

While you’re in town, the Courtyard by Marriott Lansing Downtown makes a great place to stay the night. As well as offering comfortable rooms and great service at a reasonable price, it’s right in the center of the city so sights like the Lansing Center, Michigan History Center and Adado Riverfront Park are just a short walk away.

It’s located just a couple of blocks of I-496, which you’ll join from I-69 to pass through the town, and has on-site parking, making it particularly convenient for travelers on a road trip.

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Best Summer Day Trips From Chicago

After a year at home, it’s time to hit the open road! While getting out of town for a week can sometimes be impossible, just a day away can refresh and recharge. Weve gathered up 20 summer day trips from Chicago that have kids in the car for a couple of hours and still offer up a change of scene and plenty of fun. From beaches to hikes to slides, we’ve rounded up some fun-filled day trips away from the city for the whole family to enjoy.

For more local trip ideas check out our Midwest Travel Guide or our list of the Best Lakeside Resorts for Families.

Historic And Quaint Family Fun

One of the cutest towns in the Midwest is Galena, Illinois, and its just a three-hourroad trip from Chicago. When you wander down Main Street, youll discover more than 100 charming shops and your kids will love the candy and ice cream parlors. If you have history-enthusiasts in your group, visit the Apple River Fort, which tells the tale of the 1832 Black Hawk War fought between settlers and the indigenous Sauk tribe. Also, when you take a weekend getaway from Chicago to Galena, plan to spend time outdoors. Chestnut Mountain Resort offers adventures like an alpine slide, Segway tour, and more. Alternatively, head to Fever River Outfitters and rent kayaks, paddleboards, or e-bikes. If you prefer more thrills, try a canopy zipline tour with Long Hollow Canopy Tours. Finally, for a truly unique experience, check out Hoof It and sign-up for a goat trekking experience.

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Road Trip From Chicago To Toronto

Have you ever considered taking a road trip from Chicago to Toronto? The journey will be filled with adventures and unique, scenic places to see. Traveling between these two world-class cities by road not only gives you the freedom take things at your own pace it also offers countless opportunities for impromptu stops – where the real memories are made!

The 520-mile road trip from Chicago to Toronto takes 8 hours 30 minutes to drive, and takes you past Indiana Dunes National Park, Silver Beach County Park, Lansing, South Bend, Cleveland and Niagara Falls, with endless views of the Great Lakes too.

Continue reading for our best advice and further details on the road trip from Chicago to Toronto, with ideas and inspiration on which route to take, where to stay along the way, and the best time of year to make this fantastic journey.

A Drive Along Upper Mississippi

Family Friendly Road Trip to Chicago

6 hours from Chicago

The Great River Road runs the length of the Mississippi river and you can drive part of it on a scenic road trip from Chicago.

You can join the river at Savanna or a little further down at Clinton depending on the route you take.

The route then follows the river north – you can cross in and out of Iowa and then Minnesota from Illinois and Wisconsin as the river continues to be the state border along the length of this drive.

Follow the Great River Road as it twists and turns and you will be rewarded with great views the entire way. There are plenty of places to stop and a lot of parks and trails if you want to get out of the car.

The route up to La Crosse will pass a few great stop off points – check out the steel Black Hawk Bridge over the Mississippi at Lansing and the Nelson Dewey State Park has some of the best panoramic views of the river and surrounding forests.

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Finger Lakes New York

If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don’t miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain’s Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel’s Pit BBQ, and Wagner Vineyards Estate Winery.

Drive Part Of Route 66

Route 66 is considered one of the most classic drives in America. The iconic route begins in Chicago and runs all the way to the ocean in Santa Monica, California. You probably wont have time to drive the whole thing. But you could at least do the 700 miles or so from Chicago through St. Louis to Tulsa, Oklahoma.

Add another 350 miles if you want get ambitious and make it to Amarillo, Texas to see the famous Cadillac Ranch art installation. A lot of the original highway is gone, but you can recreate most of the Route 66 route. Youll see lots of small-town Americana and roadside attractions.

Be sure to visit Pops Soda Ranch in Oklahoma, which serves hundreds of different flavors of soda pop.

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