Houston to Chicago Road Trip Through America’s Heartland

This Houston to Chicago road trip will take you through the greatest spots in America’s Heartland, including New Orleans, Jackson, and Memphis.
Written by Bonnie Stinson
Reviewed by Carrie Adkins
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
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Keep reading to learn about the greatest scenic spots on your road trip from Houston to Chicago.
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Key trip details

Houston to Chicago
​​Distance: 1,567 miles
Driving time: 24 hours
Suggested length of trip: 3 to 5 days

Itinerary

  • Houston, TX—Half a day
  • Lake Charles, LA—1 day
  • New Orleans, LA—1 to 2 days
  • Jackson, MS—One half to 1 day
  • Memphis, TN—One half to 1 day
  • Nashville, TN—1 to 2 days
  • St. Louis, MO—1 day
  • Springfield, IL—One half to 1 day
  • Chicago, IL—1 to 2 days

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.

Where to eat in Houston

  • Ninfa’s
    ($$-$$$): It’s said that Ninfa’s can be credited with popularizing fajitas in Texas — and ultimately, in the United States. Eating here is basically a historical experience.
  • Eugene’s Gulf Coast Cuisine
    ($$): Eat at this family-run oyster restaurant that specializes in Cajun flavors and seafood dishes.

What to do in Houston

A light show in Houston, TX
  • Houston Zoo
    : The 55-acre Houston Zoo in Herman Park is home to more than 6,000 animals from over 900 species. The cost of admission is around $22, but it's worth a visit while you’re in town.
  • NASA’s Johnson Space Center
    : You can’t leave Houston without visiting the NASA Space Center, which has served as a hub of space exploration for over 50 years.
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

143 miles, 2 hours
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!
To get to Lake Charles, follow the I-10 E until you reach exit 29.

Where to eat from Houston to Lake Charles

  • Steamboat Bill’s
    ($$): For a lively dining experience, check out this bustling Cajun seafood restaurant with a nautical theme.
  • Villa Harlequin
    ($$): Located in a historic building, this restaurant will be one of your best bets for Italian dishes in an intimate setting.

What to do from Houston to Lake Charles

Lake Charles, Louisiana
  • Mardi Gras Museum
    : Stop by the Mardi Gras Museum to learn about this Louisiana festival. Get a feeling of what the event is like, even if you don’t happen to be in town for it.
  • Golden Nugget
    : If you want to try your luck at one of the casinos, we recommend you try out the Golden Nugget.

Stop in—New Orleans, LA

205 miles, 3.5 hours
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.
Continue on the I-10 E and take exit 234B to arrive in New Orleans.

Where to sleep in New Orleans

  • Hotel Monteleone
    : According to the hotel’s website, it’s been said that this location marks the beginning of the French Quarter of New Orleans. Quite the majestic place to stay in town. Cost per night: from $170.

Where to eat in New Orleans

  • Cochon Restaurant
    ($$): Cochon Restaurant is a favorite among tourists and locals alike. Its name, meaning "pig" in French, hints at its specialty: pork-based dishes.
  • Mulate’s
    ($$): Get your fill of Cajun food at this world-famous eatery, then dance the night away on the dance floor inside.

What to do in New Orleans

The French Quarter, New Orleans, LA
  • Stroll the French Quarter: 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.
  • Natchez steamboat
    : This old-fashioned steamboat cruise experience will be sure to keep you satisfied with live jazz and a buffet — that includes brunch, too!
  • Take a ghost tour: Explore New Orleans’ haunted history with a spooky ghost or voodoo tour. Some great options are
    French Quarter Phantoms
    ,
    History Haunts and Carriage Tour
    , and
    New Orleans Ghost Adventures
    . It’s not all fun and festivities in this town, as you’ll quickly learn.

Stop in—Jackson, MS

188 miles, 3 hours
Jackson,
Mississippi
is another great place to stop off for a quick overnight stay, or even just to stretch your legs and eat lunch.
To get to Jackson, take the I-55 N and get off at exit 96A.

Where to eat in Jackson

  • Crazy Cat Eat Up
    ($$): Ready to eat? Check out the Crazy Cat Eat Up for some classic delta food.
  • Sugar’s Place
    ($$): Having breakfast at Sugar’s Place on Griffith Street is something you won’t want to pass up!

What to do in Jackson

The Mississippi River
  • Mississippi Civil Rights Museum
    : The Mississippi Civil Rights Museum is packed to the brim with vital history every American should take the time to learn more about.
  • Mississippi Petrified Forest
    : Hang out among ancient trees for a relaxing stroll through the Mississippi Petrified Forest. It’s bound to smell great there — like honeysuckle or pine and cedar, depending on where you are.
  • Mississippi Children’s Museum
    : Take the kids to visit the Mississippi Children’s Museum to make the trip an educational one.
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Stop in—Memphis, TN

210 miles, 3 hours
Continuing north 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.

Where to eat in Memphis

  • Soul Fish Cafe
    ($): A visit to Memphis just doesn’t feel right without stopping by the Soul Fish Cafe for great seafood.
  • Seasons 52
    ($$): For an upscale dining experience, pay a visit to Seasons 52 on Poplar Avenue, which specializes in season-specific Americana.

What to do in Memphis

The Jungle Room, Graceland
  • Sun Studios
    : While visiting Memphis, be sure to see Sun Studios, where Elvis and other famous musicians recorded a great many hits.
  • Graceland
    : Speaking of Elvis, fans of "The King" should also visit Graceland, Elvis’ stunning mansion, where you can also see his grave.
  • Beale Street
    : Music fans would be remiss not to take in a live show on Beale Street, whether or not you’re into the blues.

Stop in—Nashville, TN

212 miles, 3 hours
Nashville,
Tennessee
is another great stop on the trip. Like Memphis, Nashville is another world-famous city with deep roots in the music industry.
Follow the I-40 and take exit 209A to arrive in Nashville.

Where to stay in Nashville

  • Hutton Hotel
    : The location of this hotel — just steps away from the famed Music Row — makes Hutton Hotel a great place for a night of rest. Cost per night: from $208

Where to eat in Nashville

  • Big Al’s Deli
    ($): Nashville is famous for its food, and if you’re a foodie, Big Al’s Deli is one of the most irresistible joints on this road trip.
  • Ed’s Fish and Pizza House
    ($): 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.

What to do in Nashville

Country Music Hall of Fame
  • For country music fans: 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.
  • The Gibson Garage
    : 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.

Stop in—St. Louis MO

309 miles, 4.5 hours
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!
To get to St. Louis, follow the I-24 W, I-57 N, and I-64 W and take exit 40A.

Where to eat in St. Louis

  • Gioia’s Deli
    ($): You definitely won’t go hungry visiting St. Louis. This city has a bustling food scene with every type of cuisine you can imagine. Try the staple sandwiches at Gioia’s Deli for a casual bite.
  • Brasserie by Niche
    ($$$): For a more elegant fine dining experience, go to Brasserie by Niche. You’ll quickly learn that St. Louis is a great city to get your grub on.

What to do in St. Louis

The St. Louis Gateway Arch, MI
  • Gateway Arch
    : 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.
  • Six Flags
    : St. Louis is a very family-friendly city. There’s a Six Flags in town, which is a sure shot for a blast.
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Stop in—Springfield, Illinois

96 miles, 1.5 hours
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.
You can get to Springfield via the I-55 N and I-55BL N.

Where to eat in Springfield

  • D’Arcy’s Pint
    ($$): Ready for lunch? Try D’Arcy’s Pint, a lively diner and pub with an excellent assortment of Irish meals.

What to do in Springfield

Lincoln's Tomb, Springfield, IL
  • Lincoln Tomb
    : 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 Tomb if you’re a history buff.
  • Lincoln House
    : Lincoln lived here from 1844 to 1861 right before he became president. If you’re not a history buff, this is sure to be a cool stop anyway.
  • Lincoln’s New Salem
    : Not sick of Lincoln-themed historical sites yet? This may be the most impressive one yet — it’s a reconstruction of the town that he lived in from 1831 to 1837.

Arrive in—Chicago, IL

203 hours, 3.5 hours
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.
To get to Chicago, continue on the I-55 N and take exit 293A.

Where to stay in Chicago

  • The Robey
    : Sleep in an art deco-style former office building to rest up after arriving at your destination. It’s at an intersection with eateries and shops, and it is a short walk from the L-train if you’re over driving for a bit. Cost per night: from $135.

Where to eat in Chicago

  • The Berghoff
    ($$): Chicago’s a city with serious food game, too. The Berghoff has been in operation since 1898 and features a wide variety of German cuisine.
  • Gibson’s
    ($$$$): Gibson’s is one of the most famous steakhouses in America — get ready for a very worthwhile splurge if you end up here for dinner.
  • Giordano’s
    ($$-$$$): And don’t forget to gobble up some classic Chicago deep-dish pizza at Giordano’s! You’re in the land of deep-dish pizza, anyway. At least grab a pie for the road, although it’ll be best eaten fresh.

What to do in Chicago

The Bean at Millenium Park
  • The Bean
    : 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.
  • Magnificent Mile
    : The famed Magnificent Mile is a shopping district along Michigan Avenue that serves as Chicago’s answer to Times Square.
  • Art Institute of Chicago
    : 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.
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?

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

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