Road Trip Ideas From Chicago

Amish Country Indiana: 110 Miles East Of Chicago

In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Some people come here for classic Amish Country: 31 kinds of pie at Das Dutchman Essenhaus, hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop, treasure-hunting at the Shipshewana Flea Market. But towns like Goshen, Middlebury and Elkhart also are modern communities.

An Hour And 12 Minutes By Car

On a clear day from Michigan City, you can see Chicagos skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park in Michigan City proper, attractions include the 19th-century Barker Mansionlisted on the National Register of Historic Placesand family-friendly Washington Park Zoo.

A lighthouse in New Buffalo, Michigan

Family Weekend Getaways From Chicago In The Midwest

Categories Fun Family Trips, Travel with Kids

Wondering where to go with the family on weekend getaways from Chicago in the Midwest? There are tons of fun road trips with kids from the Chicago area. Youll love exploring all the great cities, small towns, beaches, state parks & more on family vacations for spring break, summer vacation, or quick weekend getaways.

My family and I have enjoyed visiting all the cool weekend getaways from Chicago and are excited to share which destinations you should visit next. Its amazing how many awesome travel destinations are just a short drive from Chicago.

After reading this youre sure to find the perfect weekend getaways from Chicago right here in the Midwest. So, keep reading to get inspired by our updated list of the 11 best weekend getaways in the Midwest with kids.

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Which Is The Best Method Of Transport From New York To Chicago

From the Table below we evaluated which is the best method of transport between New York and Chicago. Now this all depends on personal preference.

However, from the data its clear that the Bus is the cheapest method of transport between New York and Chicago.

So if your a real Backpacker and dont want to rent a car then this is a great option for you. However, there are a couple of negatives against taking the Bus.

There is not as much comfort and space as the train and you cant stop off as many times as you could in a car!

For more on Public transport to Chicago check out: New York to Chicago on Public Transport: Is it worth it?

Dive into our helpful comparison table below!

Find Family Fun In Branson

Driving time from Chicago: 8 hoursDistance from Chicago: 540 miles

If you’re looking for family-friendly fun, you won’t have to look farther than Branson, Missouri. This wholesome town has something for everyone. Not only is it relatively close to the Ozarks, but the community itself features amusement parks, delicious restaurants, and extensive shopping opportunities. Outdoor fun is especially popular, with zip lines and ropes courses for kids and adults alike.

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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

Waterfalls Storybook Towns Incredible Food And More Await Just A Short Drive From Chicago

Cities can sometimes feel like endless stretches of concrete especially in the hot summer months and Chicago is no exception.

Fortunately, there’s a whole world out there beyond the city limits. While it doesn’t always feel like it, there are so, so, so many worthy escapes within a few hours’ drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City’s location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You’re within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

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Be Sure To Visit Galena

Galena is a historic small town in northwest Illinois. This little town down is old school Americana at its best! Here you will find a host of 19th century buildings such as the 1826 Dowling House and Hourseshoe Mount which offers views of THREE STATES!

You can check out other ancient ceremonial sites at Casper Bluff.

Lake Michigan To South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front take a dip or two.

Do you have a favourite road trip quote? Click for the best long drive quotes to inspire your next adventure!

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Three Hours And 47 Minutes By Car

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron Riveraccessed from the 69-acre Gallup Parkor stroll U of Ms famed Matthaei Botanical Gardens and Nichols Arboretum. Be sure to make time for the citys Kerrytown Market and Shops, a picturesque neighborhood full of independent boutiques and restaurants.

An aerial view of Door County, Wisconsin

Sweet Road Trips From Chicago You Have To Take

As great as it is there are many reasons to take road trips from Chicago.

Chicago is brimming with world-class museums, live music venues, fabulous events, and international cuisine. Which is more than enough to keep you busy for weeks! Pound for pound it stands up to New York City, and Los Angeles. And thats saying a LOT!

Chicago is iconic, lively, and undoubtedly one of the best cities to visit in the United States.

However, theres a whole world waiting to be discovered just beyond the citys limits. Where will your road trip from Chicago take you?

• Detroit, Michigan

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Theodore Roosevelt National Park North Dakota

If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don’t put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

Drive Time: 14 hours

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World’s Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: TheMedora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Rooseveltâs Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

The 31 Most Awesome Road Trips From Chicago: Day Trips Weekend Getaways And Longer Excursions

Road trippers of Chicago, consider yourselves fortunate! A huge percentage of the USA is accessible within a 12-hour drive from the Windy City, so you can go just about anywhere in the Midwest or East Coast in just a day or two.

During my years living in Illinois, I took numerous road trips from Chicago. They included short trips to nearby cities like Milwaukee and Indianapolis, and longer drives to places like South Dakota and the Smoky Mountains.

Chicago may be the best city in America to take road trips from, so there are endless possibilities for car vacations. Even New York City and the west coast are within reach. It just depends how far youre willing to drive and how much time you have!

Here, Ive gathered 31 of the best road trips from the Chicago area for adventurous travelers. Some of these road trip suggestions will be obvious, like Indiana Dunes, Rockford, and Wisconsin Dells. Others may be destinations youve never considered, such as Ohios Amish Country and Kentuckys Mammoth Cave National Park.

This list of trips from Chicago is broken down into short day trips, long weekend getaways, and extended 7- to 10-day excursions.

TIP: Before hitting the road, check our list of road trip necessities. Make sure to have a dash cam and emergency road kit! And heres a post about the best food and snacks to take with you on the road.

ARTICLE CONTENTS:

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Wisconsin Cities: Milwaukee Madison Kenosha

Ive done all three of these Wisconsin cities as separate day trips, but its much tidier to combine them into a weekend getaway.

Kenosha has a surprising number of offbeat activities. One must-visit spot is the Jelly Belly Warehouse. Take a free tour and taste-test all of the companys jelly bean flavors, including the weird ones like Toothpaste, Soap, and Dead Fish.

Milwaukee has numerous attractions, like the Public Museum, Harley Davidson Museum, the Fonzie Statue, and the uniquely-shaped Milwaukee Art Museum. Madison activities include visiting the university campus and state capitol buildings and exploring the Lakeshore Path.

From Madison, take the hour-long journey west to Spring Green to visit the House on the Rock. Its hard to explain this place except to say its one of the kookiest attractions in America. Imagine a museum, funhouse, and hoarders mansion all rolled into one.

D Rock National Lakeshore Michigan

Distance from Chicago: 380 miles northeast, 6 hour driveThe upper peninsula of Michigan is a truly spectacular piece of the Midwest that is often overlooked by Chicagoans, as it does require more road time. But dont let the distance discourage you. Pictured Rocks National Lakeshore includes 42 miles of glorious views along the southern dip of Lake Superior, and really packs a punch with endless forests , and multi-colored rocky ridges with some as high as 200 feet. You wont want to miss the Miners Castle and Chapel Rock, both impressive craggy cliffs which stand apart from the rest because of their peculiar shapes and size. Whether you want to hike through the forest or bike some backroads trails, this natural paradise will keep you occupied for a long fall weekend for sure. Munising Township is stocked with restaurants, bars, and humble accommodations if fall camping doesn’t sound appealing. Also, Hiawatha National Forest is 15 miles away so you get two for the price of one.

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Elanor Bock is a Chicago born, New York-based professional dancer, writer, and renaissance woman, excelling at philosophy, mathematics, outdoor adventuring, and balancing six martinis on a tray in a crowded bar.Jay Gentile writes about food & drink, travel, events, entertainment, and culture for Thrillist.

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Michigan New Buffalo & St Joseph

What I love about going to southwest Michigan is how close it is to the city. Its only 1 1/2 hours to New Buffalo from Chicago and is easily accessible by train for quick weekend getaways from Chicago.

Youll find cute little towns dotting the coast, great beaches along the shores of Lake Michigan, yummy restaurants, shops, and tons of outdoor activities.

New Buffalo is a small town with a cute little downtown area boasting several fun restaurants and a big public beach area. Its a little quieter and laid back than St. Joseph. There are great wineries and blueberry picking in season too.

Want more action? Head a little further north to St. Joseph.

It has a larger downtown area than New Buffalo to explore with tons of shops and restaurants. There is a fun childrens museum too called Curious Kids Museum located downtown.

Plus a short walk away is a cool lighthouse you can walk out to and take pictures along the Lake Michigan Shoreline.

As you head to the beach at Silver Beach County Park, you will pass the Silver Beach Carousel and water pad area for little kids. There is also a great playground on the beach.

The best part is the St. Joseph downtown area is within walking distance of the beach so you can park once and explore the whole area.

Tip: Its a good idea to get to the beach area early in the summer months as parking fills up quickly.

When visiting this area, make sure to check out the Warren Dunes State Park and try to climb the huge sand dunes.

Find Diverse Fun In Walworth County

Driving time from Chicago: 1.5 hoursDistance from Chicago: 90 miles

No matter what kind of fun you’re looking for, you can find it in Walworth County. This southern Wisconsin region features incredible natural sites as well as charming small towns. You can venture out onto one of the local lakes in a boat, or you can ride a zip line through the forest. Even shoppers can find fun in the Lake Geneva area.

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How Far Is Denver From Chicago And How Long Will The Road Trip Take

The quickest route spans 1000 miles, and it can get you to Denver in 14 hours 20 minutes. You can theoretically do the drive in 2 days, but a better move would be to devote at least a day to each stopping point if you can.

You’ll be driving along Interstates 80 and 76 all the way to Colorado, and the former can get congested since it passes through quite a few cities. Even so, you’ll have four to six lanes to work with the entire way, so you shouldn’t expect any major holdups.

You’ll largely be driving through the Great Plains, which can be very easy on the eyes on top of being easy to drive through. You can probably get away with packing light too since there are plenty of places to stop and shop.

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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Route 6: Chicago To Springfield Illinois

Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you’ll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America’s most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World’s Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center , Henson Robinson Zoo, Illinois State Capitol, and Knightâs Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac’s Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.