Houston to Chicago Road Trip Through America’s Heartland

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  • Start in— Houston, TX
  • Stop in—Lake Charles, LA
  • Stop in—New Orleans, LA
  • Stop in—Jackson, MS
  • Stop in—Memphis, TN
  • Stop in—Nashville, TN
  • Stop in—St. Louis MO
  • Stop in—Springfield, Illinois
  • Arrive in—Chicago, IL
  • Why you need roadside assistance
  • Finding cheap car insurance
From the Gulf of Mexico to Lake Michigan, this Houston to Chicago road trip serves as a grand tour of America’s heartland. You’ll explore some of North America’s most iconic cities, including New Orleans Jackson, St. Louis, and Nashville. You’ll take in the country’s music history, fine art, and a lot of great food too.
Driving directly from Houston to Chicago takes about 16 hours, but there’s not much to do on that direct route. Little Rock, Arkansas and Memphis, Tennessee are the only big-ticket places worth exploring. So we extended your trip a little bit so that you can take your family on a fun tour through America’s heartland.
For this trip, you’ll need great roadside assistance. With roadside assistance from car insurance comparison and broker app, Jerry, you’ll be covered! This cheap and comprehensive coverage includes tire, fuel, battery, towing, and lockout services your family can depend on.
Keep reading to learn about the greatest scenic spots on your road trip from Houston to Chicago.
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Start in— Houston, TX

Houston, Texas is a very cool city to start off an epic road trip adventure. There’s a lot to see and do in Space City, from world-class zoos and museums to some of the best eateries in all of Texas.
A couple stands beneath an illuminated sign that reads "Houston" with a fluorescent skyline behind it.
A light show in Houston, TX
Try this: The 55-acre Houston Zoo in Herman Park is home to more than 6,000 animals from over 900 species. Your kids won’t want to miss out on the Children’s Museum of Houston, a fun interactive space encouraging educational play. And you can’t leave Houston without visiting NASA’s Johnson Space Center.
Eat here: Like any big city in Texas, Houston has incredible food! Ninfa’s on Navigation Boulevard is said to be the birthplace of the fajita. Eugene’s Gulf Coast Cuisine serves up dishes that are local to the Gulf region. And if you’re in the mood for fine dining, be sure to try State of Grace, Turner’s, and Xochi.

Stop in—Lake Charles, LA

Lake Charles, Louisiana. is a cool little town with some beautiful beaches, as well as some of America’s best Cajun food. If you’re not traveling with kids, the Lake Charles casinos are lots of fun, too. Just make sure you leave with enough money for the rest of your trip!
Travel time: 2 hours and 22 minutes
A pastel sunset over the port of Lake Charles.
Lake Charles, Louisiana
Try this: Stop by the Mardi Gras Museum to learn about this Louisiana festival. If you want to try your luck at one of the casinos, we recommend you try out the Golden Nugget. And if you want to soak up the sun, why not head over to Holly Beach?
Eat here: Steamboat Bill’s is a nautical-themed Cajun seafood restaurant with portions that will leave you asking for a doggy bag. And if you’re more in the mood for something upscale, try the chic Villa Harlequin restaurant for refreshingly modern Italian food.

Stop in—New Orleans, LA

New Orleans is one of those cities everyone should try to visit at least once in their lifetime. There is no place quite like The Big Easy. Lively music erupts from every corner. The buildings are staggeringly gorgeous. And the food? You’d be hard-pressed to find better eateries anywhere in the United States.
Travel time: 3 hours and 5 minutes
A group of street performers play instruments in the French Quarter.
The French Quarter, New Orleans, LA
Try this: While visiting New Orleans, it’s only natural to want to B-line straight toward the legendary French Quarter. This is the spiritual home of jazz music, which echoes from every brick your feet touch. And the buildings are some of the most gorgeous structures you’ll find anywhere in North America.
Be sure to schedule a trip on the Natchez steamboat, and explore New Orleans’ haunted history with a spooky ghost or voodoo tour.
Eat here: The Cajun food here makes the French Quarter a foodie paradise, and the Cochon Restaurant is a favorite among tourists and locals alike. Also try Mulate’s, another world-famous eatery. And when it’s time for the next leg of your trip, stop by Mother’s on Poydras Street and get yourself a po boy sandwich for the road.

Stop in—Jackson, MS

Jackson, Mississippi is another great place to stop off for a quick overnight stay, or even just to stretch your legs and eat lunch.
Travel time: 2 hours and 50 minutes
A stormy sky behind a bridge over the Mississippi River.
The Mississippi River
Try this: Take the kids to visit the Mississippi Children’s Museum and the Mississippi Petrified Forest. The Mississippi Civil Rights Museum is packed to the brim with vital history every American should take the time to learn more about.
Eat here: Ready to eat? Check out the Crazy Cat Eat Up for some classic delta food. And having breakfast at Sugar’s Place on Griffith Street is something you won’t want to pass up.
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Stop in—Memphis, TN

Travel time: 3 hours
Continuing North on I-55 will lead you to another big tourist destination: Memphis, Tennessee. Memphis is famous for its contributions to popular music, with a long list of globally famous musicians having been born here, from B.B. King to Elvis Presley to Justin Timberlake.
Try this: While visiting Memphis, be sure to see Sun Studios, where Elvis and other famous musicians recorded a great many hits. Speaking of Elvis, fans of “The King” should also visit Graceland, Elvis’ stunning mansion, where you can also see his grave. And music fans would be remiss not to take in a live show on Beale Street.
Eat here: A visit to Memphis just doesn’t feel right without stopping by the Soul Fish Cafe for great seafood. For an upscale dining experience, pay a visit to Seasons 52 on Poplar Avenue, which specializes in season-specific Americana.

Stop in—Nashville, TN

Nashville, Tennessee is another great stop on the trip. Like Memphis, Nashville is another world-famous city with deep roots in the music industry.
Travel time: 3 hours
A sculpture in front of the Nashville skyline at sundown.
Nashville, TN
Try this: For country music fans, the pilgrimage to Nashville is irresistible. From the Grand Ole Opry to the Country Music Hall of Fame, Nashville is to country music what New Orleans is to jazz. The blues is a popular genre with deep ties to Nashville, too.
Are there any guitarists in your family? Gibson Guitars calls Nashville home, too. While the company was originally founded in Kalamazoo, Michigan, Nashville is presently the company’s world headquarters. No guitarist should leave Nashville without having visited the Gibson Garage.
Eat here: Nashville is famous for its food, and if you’re a foodie, Big Al’s Deli is one of the most irresistible joints on this road trip. You might also consider paying a visit to Ed’s Fish and Pizza House. Just don’t expect to find pizza on the menu. Strange, we know. But if you don’t mind waiting in line for a while, get yourself a Whiting sandwich to go.

Stop in—St. Louis MO

St. Louis, Missouri is a place you’ll want to visit for more than just the break from driving. It’s a great tourist destination with lots to see and do!
Travel time: 4.5 hours
The St. Louis Gateway Arch and State Building in this daytime skyline scene.
The St. Louis Gateway Arch, MI
Try this: St. Louis is home to the famous Gateway Arch, a 630-foot stainless steel monument. You can actually take a ride up into the arch itself and see a stunning view of St. Louis from the summit. If you’re not afraid of heights, this is something you definitely want to check out.
St. Louis is a very family-friendly city. There’s a Six Flags amusement park, a zoo, and an aquarium. And the Magic House is an exciting interactive children’s museum where your kids can explore a life-size replica of the Oval Office.
Eat here: You definitely won’t go hungry visiting St. Louis. This city has a bustling food scene with every type of cuisine you can imagine. From the staple sandwiches at Gioia’s Deli to the elegant fine dining of the Brasserie by Niche, St. Louis is a great city to get your grub on.
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Stop in—Springfield, Illinois

Springfield, Illinois is a great place to stop briefly and spend a little time sightseeing. It’s a fun stop for a rest, especially if you’re an American history buff.
Travel time: 1.5 hours
![alt text](https://s3-us-west-2.amazonaws.com/jerry-uploads-prod/article/images/lincolns-tomb-springfield-il_t20_yRrQN2.jpg “Lincoln’s Tomb, Springfield, IL) Lincoln’s Tomb, Springfield, IL
Try this: Springfield is the hometown of America’s 16th President, Abraham Lincoln. And the city celebrates his life just about everywhere you go, too. You’ll want to see the Lincoln Tome, the Lincoln House, Lincoln’s New Salem, and the Abraham Lincoln Presidential Library.
Eat here: Ready for lunch? Try D’Arcy’s Pint, a lively diner and pub with an excellent assortment of Irish meals.

Arrive in—Chicago, IL

You’ve reached the final destination on this epic Houston to Chicago road trip: Chicago. The Windy City is the third biggest metropolis in the United States, and it’s easy to spend a lot of time here. But there are some must-see locations every tourist needs to visit.
A marquee in Chicago announces Pixies to perform.
Chicago, IL
Travel time: Let’s take the scenic route, shall we? This brief three-hour trip concludes on the final stretch of The Mother Road, Route 66. You can take Interstate 55 to get to Chicago a little quicker, but where’s the fun in that?
Try this: Getting your photo taken in front of The Bean in Millenium Park—it’s actually called “the Cloud Gate”—is a must for Chicago visitors. The famed Magnificent Mile is a shopping district along Michigan Avenue that serves as Chicago’s answer to Times Square.
Ferris Bueller fans should visit the Art Institute of Chicago and stare longingly at Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.” Daydreaming about how angry your father will be about “borrowing” his Ferrari is optional.
Eat here: Chicago’s a city with serious food game, too. The Berghoff has been in operation since 1898 and features a wide variety of German cuisine. Gibson’s is one of the most famous steakhouses in America. And don’t forget to gobble up some classic Chicago deep-dish pizza at Giordano’s!

Why you need roadside assistance

Like with any big road trip, you’ll want to make sure your car is in good shape before you start driving. Check your oil, top off your fluids, and make sure your tires and brakes are in good order. And if a roadside emergency does happen, having roadside assistance you can rely on will really save your whole vacation.
The Jerry app offers a roadside assistance program that will keep you and your family safe from the Houston bayou to the bay buildings of Chicago. With fuel delivery, tire assistance, battery services, towing, and more, Jerry’s roadside assistance will be standing by 24/7 to help you out of an otherwise nerve-racking roadside crisis.

Finding cheap car insurance

And hey, since you’re downloading the Jerry app and signing up already (it takes less than a minute to register), why not take the opportunity to shop for car insurance? Jerry will gather up to 50 car insurance quotes for you to browse.
And when you find a plan you like, Jerry can eliminate the paperwork and phone calls and even cancel your old policy for you!
Jerry blew my mind, honestly. From start to finish, using the app took me 10 minutes and I ended up with $100 of savings a month. Best of all, customer service answered all my questions about rental car reimbursement and roadside assistance.” ––Savanna R.
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