Best Road Trips In Illinois

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  • Chicago, IL
  • Chicago IL
  • Springfield, IL
  • Galena, IL
  • Kewanee, IL
  • Tunnel Hill, IL
  • Rockford, IL
  • Oglesby, IL
  • Savanna, IL
  • Why you need roadside assistance
  • Finding cheap car insurance
The Land of Lincoln is full of road trip possibilities—take in Chicago’s sights and cuisine, cruise along Route 66, visit Springfield for all things Abe Lincoln-related, see charming small towns and public art, and explore the amazing natural wonders Illinois has to offer.
Road tripping through Illinois can be a blast—so long as your trusty car doesn’t break down on the highway. Put your fears at ease and with Jerry’s roadside assistance program. Not only will you have access to towing, winching, and other member benefits, but the program costs just $6.99.
Marry a roadside assistance membership with a car insurance plan through Jerry and you’ll have found a true deal.
For more on the best Illinois road trips, keep reading!
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Chicago

Why you should go

Chicago delivers incredible architectural, cultural, and food highlights. Spend one day in the Windy City, and you’ll be doing the ‘85 Bears Super Bowl Shuffle down Michigan Avenue, no doubt!

What you should do

Chicago is truly an architectural marvel. First, check out the delightfully quirky Cloud Gate sculpture (affectionately known as “The Bean”) in Millenium Park, just north of The Art Institute of Chicago.
Go on the official Architecture Foundation Center River Cruise aboard The First Lady. On the tour, you’ll be gawking at Willis Tower, The Wrigley Building, Marina City, and other concrete-and-glass gems.
Once the tour is done, head over to The John Hancock Tower, and book it to the 94th floor observation deck for panoramic views. Or, shop til you drop on Chicago’s famous Magnificent Mile.

Where you should eat

With all that sightseeing, you’re going to be hungry. Heed your stomach’s call with a Chicago classic—deep dish pizza at Pizzeria Uno on the North Side, which has been slinging pies since 1943.
Later on, if you’re hankering for late-night eats, head to The Wiener’s Circle in Lincoln Park for char dogs. If it’s a weekend late-night, bring your best insults—staff and customers at this local institution are known to exchange profanities as orders are being placed.
A bright yellow ferry chugs along the Chicago river downtown in the fog.
Downtown Chicago, IL

Route 66

Why you should go

The famous Route 66, also known as The Mother Road, begins in Chicago and ends 435 miles away in Santa Monica, California.

What you should do

There are plenty of highlights to see as you ramble along Route 66 (officially known as I-40 since 1985).
In Joliet, west of Chicago, you’ll see the old prison used in the movie Blues Brothers. In Pontiac, Illinois, make a stop at the Route 66 Hall of Fame, home to memorabilia and stories of one from the most important and iconic highways in the country’s history.

Where you should eat

Along Route 66, you’ll pass numerous historic motels, such as The Wagon Wheel, and its classic neon signs in Cuba, Missouri. Grab some grub at a classic Route 66 diner for some authentic Midwestern comfort food, like the towering Horseshoe Dish at Charlie Parker’s in Springfield.
A blue, orange, and golden sunset along the highway in Cuba, Missouri.
Cuba, Missouri

Springfield

Why you should go

Visiting Springfield, the state’s capital city, is a great chance to burnish your knowledge of Illinois legislative minutiae and learn all you ever wanted to know about Abraham Lincoln, America’s 16th President.

What you should do

Your first stop should be The Lincoln Presidential Library, for the official account of Lincoln’s Presidency and documents related to his time in office. You also can visit the Lincoln Home National Historic Site to see the only home that Honest Abe ever owned.
Though offered seasonally, take the Lincoln’s Ghost Walk: Legends and Lore tour for fun and fascinating insights into the life of one of the country’s most important leaders.
Visit the State Capitol Building (the tallest one in the country, topping The U.S. Capitol in D.C.), where tours of the exterior are offered.

Where you should eat

Give yourself a break from the historical tidbits and indulge in a mouthwatering “original” corn dog at Cozy Dog’s Drive-In, where the deep-fried hotdog-on-a-stick has been served since 1946.

What fans of The Simpsons might want to do

If you’re a fan of the TV show The Simpsons and you’ve got some time on your hands, take a drive an hour east from Springfield to Shelbyville—just to say you did it.
Mossy caves amidst the forest outside of Springfield, Illinois.
Springfield, Illinois

Galena

Why you should go

Galena is a charming small town brimming with Americana, and it was also home to a Civil War hero.

What you should do

Visit Galena’s beautiful 800-building historic district, listed on the National Register of Historic Places. You’ll find loads of shops to visit and many restaurants at which to grab a bite.
Don’t miss out on the Ulysses S. Grant Home State Historic Site, where the Civil War hero and the country’s 18th President lived following his return home from the war in 1865. Do note—the original furnishings remain in the home, so if you’re wondering whether you’re allowed to sit in President Grant’s favorite chair, the answer—unfortunately—is no.
If you’re going to stay the night in Galena, you can’t sleep in President Grant’s bed. But you can rest your head at The Desoto House Hotel, Illinois’ oldest hotel, which has been open since 1855.
The red brick exterior of the Desoto House Hotel, with bright red letters indicating the hotel name and restaurant inside.
Galena, Illinois

Kewanee

Why you should go

Visit Kewanee for amazing murals painted by an international group of artists.

What you should do

Take the guided History of Paint Tour to check out the 15 incredible murals on downtown Kewanee buildings, celebrating the city’s past, present, and future. The murals were created in 2013 after an internationally-renowned group of muralists came to town. Though all the murals are incredible, Sandy’s Fast Food Chain and Roger Reimer are standouts.
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Shawnee National Forest

Why you should go

Shawnee National Forest is 280,000 acres of resplendent natural wonders.

What you should do

Explore seven wilderness areas in Shawnee, and don’t miss out on The Garden of Gods—stunning ancient sandstone rock formations. You can even camp under them, too!
For some exercise, hike the River To River Trail, which connects the Ohio and Mississippi rivers on a 160-mile trek.
Also be sure to hit Inspiration Point for incredible, scenic views.
A couple stands atop a rounded rock overlooking the Garden of the Gods in Shawnee National Forest.
Shawnee National Forest, Illinois

Anderson Japanese Rock Gardens

Why you should go

Visit Anderson Japanese Rock Gardens, one of the most stunning and authentic Japanese gardens in North America.

What you should do

Immerse yourself in the beauty of this spot in the heart of Rockford, where you’ll find beautiful waterfalls, intricate rock gardens, opulent bridges, and a charming, traditional Japanese tea house. Be sure to take time for a moment of Zen.
A lake in the Japanese Gardens of Rockford, with a patio, pines, and Japanese maple visible among the foliage.
Rockford, IL

Matthiessen State Park

Why you should go

If you’re intent on keeping your distance from other people, visit Matthiessen State Park for a variety of beautiful wide open spaces.

What you should do

Wander through Matthiessen’s diverse natural settings—you’ll find canyons, waterfalls, rock formations, and even prairies as you meander through the park.
In the summer, Matthiessen is perfect for forest hikes. In the winter, there are plenty of trails for snowshoeing and cross country skiing.
A concrete bridge slick with translucent ice in the winter at Matthiessen State Park in Ottawa, Illinois.
Matthiessen State Park, Illinois
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Mississippi Palisades Park

Why you should go

Mississippi Palisades Park is located at the meeting point between the Mississippi and Apple Rivers, and it offers both summer and winter activities, including rock climbing.

What you should do

Hiking is a must—you’ll pass by huge cliffs, through limestone caves, and across forested ravines. In the winter, Palisades is perfect for snowshoeing and cross country skiing across both groomed and ungroomed trails.
Rock climbers love the Palisades, especially the popular climbing spots Twisted Sister and Indian Head.
The sun sets above a rocky riverside area of Savanna, Illinois
Savanna, Illinois

Why you need roadside assistance

Before you cross Illinois, do yourself a favor and sign up for [Jerry]’s (https://getjerry.com/signup) roadside assistance program. It costs just $6.99, and you’ll be covered for tire fixes, towing, emergency fuel delivery, winching, and more. Members receive a slew of benefits, including Uber credits!

Finding cheap car insurance

Car insurance is required in nearly every state, so if you’re looking for the best deal, Jerry will help you find it.
This intelligent car insurance broker and comparison shopping app is built for quickly finding you the best deal on car insurance. Not only will Jerry sign you up for your new policy and cancel your old one, but the app will also automatically search for new rates for you before each renewal period.
Best of all, Jerry users save an average of $879 on car insurance each year!
“I’ve been dealing with agencies and quote websites for the longest time and Jerry made it easier than it’s ever been. In a matter of minutes, I was able to get multiple quotes, cancel my policy, start my new one, save $230 a month!” - Satisfied Jerry user
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