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Best Road Trips From Chicago

Enjoy Endless Activities In Traverse City

Chicagos Best Road Trips 2 Show Open

Driving time from Chicago: 4.5 hoursDistance from Chicago: 320 miles

When you visit Traverse City, Michigan, at the end of a road trip from Chicago, you can enjoy a wide variety of activities for the whole family. Whether you’re looking to immerse yourself in the local culture of the city or spend time along the water for a scenic sunset, there’s never a shortage of beauty or entertainment here.

Oglesby And Utica Illinois

1 hour 30 minutes from Chicago

The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. Oglesby and its neighbor Utica lie nestled into a curve of the Vermilion River and is perfect for exploring some of the best outdoors in Illinois.

The main attractions are the two major parks – the Starved Rock State Park and the Matthiessen State Park.

While both parks are not as large as some, there is plenty to explore with trails going through canyons and some amazing rock formations.

You can easily do a day trip from Chicago, but if you decide to come for the weekend, you can stay over at the Starved Rock State Park Lodge that comes complete with a pool and spa to unwind after your hiking.

Make sure you grab some food at the Root beer Stand. This Mom n pop classic fast food diner has been in Oglesby since 1955 and serves top notch root beer floats and burgers.

Do I Really Have To Go Back Home

Yes, even this step is optional, because if you’re on vacationwho wants the trip to end? It’s okay, you can start planning yournext trip!

Want to plan the trip back? Get the reverse directions for aMaine to Chicago drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you’re flying or drivingby calculating the distance from Chicago to Maine. Or get a full Chicago to Maine flight plan.

Don’t forget about exploring your own hometown with a staycation.You can also find some cool day trips or get away for a weekend.Maybe try typing in a faraway location like London, Hong Kong,or Sydney, and get inspired for your dream trip around the world.

And if you know Chicago well, please help your fellowtravelers and answer their questions about Chicago!

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Ann Arbor To Relive Your College Days

3.5 Hours from Chicago

Home to the University of Michigan, Ann Arbor is the perfect place to forget the real worlds stresses and act like a college kid again. You can tour the campus, visit one of the 16 on-campus museums, stroll the Matthaei Botanical Garden and Nichols Arboretum (the Arb to locals, catch a football game at The Big House, or simply drink the day away. Catch some live music at The Ark, peruse the Ann Arbor Farmers Market, tour a local craft brewery, and grab a bite from the iconic Zingermans Deli.

Its a bit of a choose your own adventure as there is kayaking, canoeing, tubing, and stand-up paddleboarding on the Huron River in the summer, and cross-country skiing, snowshoeing, and ice skating in the wintertime.

Where to Stay: Close to campus, most hotels are easy and accessible for visiting students and parents, but if youre looking for more of an urban retreat, you can also pop over to Detroit for the evening.

Day Trips From Chicago: Naperville

20 Best Road Trips From Chicago

Naperville is a prairie town turned award-winning small city that has earned accolades from Money Magazine Best Places to Live, Kiplinger Best Places for Early Retirement, Zero Population Growth Top Five Kid-Friendliest Cities, and many others.

Besides Napervilles small town charm, the best reason for a day trip here is Riverwalk, the citys 1.75-mile walkway along the DuPage River. Highlights include Moser Tower a beautiful 158-foot bell tower, a clock tower, three fountains, a covered bridge, heritage sculptures, an amphitheater and labyrinth, and paddle boats. Visitors can also visit the popular Centennial Beach and Grill, a sandy beach waterpark and restaurant.

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Chicago Illinois United States

Chicago is an appropriately exciting spot to start your road trip. From the views atop Sears Tower , to the hustle and bustle of Navy Pier, to the fun to be had at Oak Street Beach , Chicago is an awesome place to explore before or after a road trip. Kinzie Hotel, Sutton Place, and the Freehand are some of the coolest hotels in Chicago if you need a place to stay, and you can fill up your tanks at Ginos East, Als, and Glazed and Infused before you head out for Cleveland.

Road Trips From Chicago: Old State Capitol State Historic Site

The Greek Revival-style Old State Capitol, completely reconstructed in Springfield, Illinois, is dedicated to the legacy of Abraham Lincoln. Its where he delivered his famous House Divided speech, and where, following his assassination, he lay in state on May 3rd and 4th in 1865.

Visitors can watch a 15-minute video in the audio-visual theater describing the history of the Old Capitol prior to touring it on either a self-paced tour or a 30-minute docent-led tour. Special events at the Old Capitol include the Abraham Lincoln Symposium, Holocaust Remembrance Day, an Annual Civil War Encampment, and the Old Capitol Art Fair.

Old State Capitol Plaza, 6th and Adams Streets, Springfield, IL, Phone: 217-785-7960

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Summary: Its So Easy To Find Road Trips Near Me

While living in Chicago, it was incredible that I had so many road trip destinations near me. This list doesnt even cover them all.

Other possibilities include short Illinois road trips to places like Springfield, Champaign, and Peoria. The Abe Lincoln Home National Historical Site in Springfield is particularly noteworthy.

If youve got at least 5 days on your hands, consider other weekend trips from Chicago to Memphis, Atlanta, Charlotte, or Virginia Beach. Make this the summer of the road trip!

And if you want to get really crazy, heres a detailed guide to driving from Chicago to Seattle

Do you have any other suggestions for great road trips from Chicago?

Best For Beaches: New Buffalo Mi

Chicagos Best Road Trips: Show Open

Travel Time: One hour and 15 minutes from Chicago

When to Go: June through September

What to Do: During a beach weekend, we encourage doing as little as possible. While away the hours sunning yourself or reading a good book on the long, peaceful beaches. After sunset, head to Redamaks for the Velveeta burger, a gloriously gooey masterpiece that has become something of a legend since the restaurant opened in the 1940s. If you need something a little more exciting, theres always the Four Winds Casino.

Where to Stay: How does a luxurious lakefront home with a hot tub sound? Not only is it within walking distance to New Buffalo downtown , its also super close to the beach.

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Indiana Dunes National Lakeshore Indiana

PC: Wikimedia.com

Considered as one of the top places to visit near Chicago in summer, Indiana Dunes National Lakeshore along with the park appeals to families who are looking for a picnic destination from Chicago. Hugging the Lake Michigan is the Indiana Dunes National Lakeshore with its rugged dunes, inviting pastures, and winding rivers, that offers plenty of activities based on the season.

Make a quick stop at the visitor’s centers to grab the map of the area and gain info on the terrain.

Go hiking or hire a bike and ride through the trails, take up the Three Dune challenge to climb up the trees, and enjoy the mesmerizing view of the Lake.

Time Taken: 1 hour 2 minutes approximately

Two Hours And 47 Minutes By Car

Voted Beer City USA in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail, a map showcasing all of the options in the city. For food, were partial to strolling Downtown Market, which counts more than 20 vendors in the hall south of Heartside Park . For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park: here, youll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

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Weekend Getaways From Chicago: Sevenoaks

If you are looking for romantic places to visit near Chicago, SevenOaks offers 9 adult-only luxuriously appointed cottage suites. The one-floor buildings have charming front porches, stone fireplaces, comfortable living rooms, and king-sized beds with luxury linens.

The garden has a soothing water feature, fire pit and comfortable lounging chairs. Just a short walk from downtown Lake Geneva, guests have easy access to a number of restaurants. Play a round of golf, visit a day spa, go biking, hiking or skiing in the winter. Rates start at $179 per night.

682 S. Wells Street, Lake Geneva, WI 53147, 262-248-4006

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The 5 Best Road Trips From Chicago

10 Best Weekend Road Trips From Chicago, Illinois in 2021 ...

Its amazing how quickly three hours go by when that next episode button keeps popping up. But with the same amount of time in the car, you can transport yourself to romantic retreats, majestic waterfalls and wineries. Forget battling the security lines at OHarethese five road trips are our top picks for your next weekend getaway.

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Portland To Astoria: An Oregon Coast Road Trip For Outdoor Lovers

If you love the outdoors, then this six-day road trip along the coast of Oregon is for you. After driving to Coos Bay from Portland, travelers will meander along Oregons dramatic, rocky coastline, discovering geological features, evergreen forests, seaside dunes, and marine ecosystems along the way. Between stops, there are ample opportunities to stretch your legs hiking, kayaking, or strolling around the regions small townslike the historic old town in Florence. Of course, it wouldnt be an Oregon road trip without a stop at a craft brewery, such as Fort George Brewery in Astoria, or cozy coffee shop, like Bread & Roses in Yachats.

Plan your trip

Day Trips From Chicago: North Utica

North Utica is a sleepy river town along the Illinois-Michigan canal and nearby Illinois River that will appeal to antique, wine, and nature lovers. Visitors will find wineries and wine shops, antique stores, flea markets, rustic furniture and collectibles shops, and a pottery studio.

You can learn about the towns history at the LaSalle County Historical Museum, and dine at popular eateries like Cajun Connection and Canal Port Bar & Grill. Grand Bear Resort has inexpensive day passes to their 24,000-foot indoor waterpark, as well as a restaurant, sports bar, and sweet shop. Four nearby state parks provide outdoor recreational opportunities.

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Milwaukee For Brews And Tunes

1.5 Hours from Chicago

Known as the mini Windy City, Milwaukee is another great weekend trip from Chicago for a less chaotic version of the big city. An up and coming cosmopolitan hub, their food, beer, and music scene is quickly becoming a magnet for millennials thats infinitely cheaper than Chicago. And as a bonus? You dont even have to drive if you dont want to, as the Amtrak train goes right there.

Art aficionados can pay a visit to the Milwaukee Art Museum. History or beer buffs can spend a few hours at the Pabst Mansion. Animal lovers can say hello to all the friendly friends at the Milwaukee County Zoo. And motorcycle enthusiasts can spend an entire day at the Harley-Davidson Museum.

And while those activities are ideal for the daytime, enjoy the brews and tunes after dark. For a night of fantastic drinks and equally amazing music, stop by Company Brewing, Anodyne Coffee Roasting Company, or Milwaukee Ale House. Youll definitely want to visit during Summerfest, which boasts two-weeks of back-to-back concerts on the lake.

Where to Stay: Milwaukee has a huge range of accommodation options, from penthouse apartments to trendy b& bs downtown.

St Louis For An Urban Escape

Chicago’s Best Road Trip Spots

4.5 Hours from Chicago

Many people overlook St. Louis as an old and historical city, but it actually has amazing up-and-coming art and culture scene.

Of course, one of the best things to do in St. Louis is to visit the iconic Gateway Arch, which you can climb inside. This 630-foot stainless steel structure was built in 1963 and celebrates the westward expansion of the United States.

And while visiting the Gateway Arch should be at the top of your St. Louis bucket list, there are plenty of other activities that youll want to add to your itinerary. Explore the new Union Station and see the city from the Wheel, experience the brand-new virtual reality ride at the St. Louis Aquarium, tour the insane architectural wonder that is City Museum, stop and smell the roses at the Missouri Botanical Garden, explore the 1,300 acres of St. Louis Forest Park, and admire the Cathedral Basilica of St. Louis.

To make your visit to St. Louis one of the best road trips from Chicago, you can add a few stops on your way like Peoria and Springfield, which are part of the iconic Route 66.

Where to Stay: The Angad Arts Hotel is a super cool boutique property that lets you book rooms by color to control your vibe looking for romance? Go red. Want to relax? Choose blue. Its totally up to you!

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