Visit numerous iconic cities and attractions as you drive from urban America through the countryside and mountains, all the way to the Atlantic Ocean.

A road trip from Chicago to Myrtle Beach covers four distinct types of landscape: bustling cities, peaceful countryside, dramatic mountains, and sandy beaches. You’ll find loads of iconic spots—and a fair few hidden gems—as you head southeast!

With the help of

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comparison and broker app with help from

Jerry

, here’s an itinerary that will let you hit all four over the course of a week! From where to eat and sleep to what to do, Jerry’s got you covered.

And part of that coverage is great roadside assistance! There’s nothing worse than being stuck in the middle of nowhere with a flat tire, cracked windshield, or an empty tank. For just $6.99,

Jerry

offers an excellent program to give you peace of mind as you hit the road.

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Key trip details

Distance: 1,074 miles

Driving time: 17 hours and 16 minutes

Suggested length of trip: 3 to 5 days

This is definitely a trip that requires some rest along the way, so why not take advantage of the drive and get the most out of every stop? Feel free to add time to any city on the way there or back.

Itinerary

Chicago, IL—Half a day

Indianapolis, IN—1 to 2 days

Louisville, KY—Half a day

Nashville, TN—Half a day

Asheville, NC—1 to 2 days

Myrtle Beach, SC—1 to 2 days

Chicago to Indianapolis

183 miles, 3 hours

You could spend weeks exploring everything the Windy City has to offer. From delicious cuisine to fascinating museums, it’s a sprawling metropolis easy to lose yourself in.

But we’ve put together some quick hits, including the Field Museum and foodie necessities. Day one finishes with a drive to Indianapolis to get your journey started in earnest.

To get to Indianapolis, follow the I-90 E and I-65 S, then take exit 113.

Where to stay from Chicago to Indianapolis

Freehand Chicago

: If you need to spend the night, Freehand Chicago is one of the city’s trendiest, most interesting hotels. Comfortable accommodations and delicious dining make this a great option. Cost per night: from $117.

Ironworks Hotel

: Once you reach Indianapolis, bed in at this cool-looking spot, inspired by America’s industrial heritage. It’s located just outside the city in historic downtown Beloit. Cost per night: from $189.

Where to eat from Chicago to Indianapolis

Bryn Mawr Breakfast Club

($$): Eat breakfast at Bryn Mawr Breakfast Club in Chicago. They have a unique acorn squash & tofu plate—a really interesting and tasty veggie option!

Saucy Porka South Loop

($): For lunch, you can’t go wrong with this Chicago eatery! It’s an Asian-Latin fusion food truck-style spot, famous for its tacos and banh mi.

Mimi Blue

($-$$): Grab dinner here in Indianapolis, a quirky meatball bar with vegan options. Mix and match meatballs with different sauces for a plate that’s uniquely yours.

What to do in Chicago

Field Museum

: Take a look around this popular Chicago museum. It’s one of the best museums of natural history in the US—highlighted by "Sue" the T-Rex. Basic admission will cost you $26.

Millenium Park

: If you have time before you get going to Indianapolis, head to this iconic Chicago staple—picture in front of The Bean optional!

Indianapolis to Louisville

115 miles, 1.5 hours

Have a look around Indianapolis before heading south to Louisville. Along the way stop at Muscatatuck Wildlife Refuge, which boasts a whopping 8,000 acres of wetlands and nature.

After leaving Indianapolis, follow the I-65 S to S 9th St/Roy Wilkins Ave.

Where to stay in Louisville

Vu Guesthouse

: Don’t be misled by the strange facade of the Vu Guesthouse. The hotel is a converted tobacco factory that now has 34 rooms and a coffee lounge, and it’s a great pick for your night in Louisville. Cost per night: from $143.

Where to eat from Indianapolis to Louisville

Cafe Patachou

($$-$$$): Enjoy breakfast at this spot in Indianapolis, dubbed a "student union for adults." It features tons of fresh ingredients, delicious eats, and a warm atmosphere.

Brown Hotel

($$-$$$): Hit up the dining room at the Brown Hotel for a signature Louisville "Hot Brown"—an open-face turkey sandwich covered in melted mozzarella.

What to do from Indianapolis to Louisville

Muscatatuck Wildlife Refuge

:Stop here along highway 50 in Seymour, Indiana. While you’re exploring nature at its finest, keep your eyes peeled for bald eagles and turtles in the wetlands.

Louisville Slugger Factory and Museum

: Once you get to Louisville, explore on foot before dipping into this museum for a primer on baseball history. Stop into Sunergos for a coffee and pastry pick-me-up.

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Louisville to Nashville

175 miles, 2.5 hours

Drop into the Muhammad Ali Center in Louisville before meandering further south to the Music City—with a brief stop for some more beautiful landscapes on the way!

The I-65 S is your fastest route to Nashville—just be sure to take exit 48 from I-24 E.

Where to stay in Nashville

The Russell

: A converted church with funky rooms and stained glass windows—a fun pick for your two nights in Nashville. A portion of your nightly rate will be donated to local nonprofits fighting homelessness. Cost per night: from $233.

Where to eat from Louisville to Nashville

Wild Eggs

($$): Tuck into breakfast at this Louisville destination, a midwestern chain specializing in hearty American food.

Spelunkers Cafe

($): Grab a quick lunch here in Mammoth Cave National Park, a spot for a quick salad or sandwich after you’ve explored the caves.

FOLK

($$-$$$): Once you get to Nashville, finish your day at this specialty pizza spot, serving innovative dishes in a classy, chill space.

What to do from Louisville to Nashville

Muhammad Ali Center

: A celebration of the life of the renowned boxer and Louisville native. Allow yourself a couple of hours to explore the museum, which has plenty to offer both adults and kids.

Mammoth Cave National Park

: About an hour outside the city, enjoy a guided tour around the caves at one of the world's longest known cave systems. At more than 412 miles, it’s the largest known cave system in the world!

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A day in Nashville

The music city presents a number of options for music and sightseeing. Explore the roots of country music before checking on the city’s quirky cultural features.

Where to eat in Nashville

Biscuit Love

($-$$): You have to try this iconic destination for breakfast. Get the bonuts to share—you definitely won’t be disappointed!

Cafe Roze

($$): For something a little lighter, stop for lunch at this hip, all-day cafe to enjoy fresh salads and healthy sandwiches.

Lou Nashville

($$): There’s no better dinner spot for you to finish your day in Nashville. You can’t go wrong with anything from their menu of American fare (and their extensive wine list—after all, you’re on vacation!).

What to do in Nashville

Country Music Hall of Fame

: Country music fan or not, you’re in Nashville—so drop by the Country Music Hall of Fame in the morning to learn about the origins of some of America’s most famous music.

Parthenon

: This is a near-full size replica of the famous Athenian building that shows the city’s art and culture. It also houses sculptures and paintings by 19th- and 20th-century American artists.

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Road trip essentials

Nashville to Asheville

294 miles, 4.5 hours

For your first major change in scenery, switch urban Nashville for secluded Asheville. Drive to a secluded city in the heart of Appalachia for the night—and get your hiking boots ready!

You just have to take the I-40 E to Patton Ave once leaving Nashville.

Where to stay in Asheville

Princess Anne Hotel

: Get some rest at this historic building that opened in 1924 and offers warm, cozy accommodations at good rates. Cost per night: from $215.

Omni Grove Park Inn

: If you want something fancier—and a little more expensive—go for this highly regarded inn. It’s understated elegance and southern charm make it one of the most celebrated hotels in the nation. Cost per night: from $332

Where to eat from Nashville to Asheville

The Tomato Head

($$): For lunch, stop in Knoxville—about halfway between Nashville and Asheville—and grab a slice of yummy pizza from The Tomato Head.

Chiesa

($$): A good option for dinner., with great pasta dishes on the menu. It’s also in the Montford District, a cool place to stretch your legs after a big meal.

What to do in Asheville

Take in the Great Smoky Mountains: The last hour of your drive to Asheville is one of the prettiest drives in America, cutting through these mountains and into Appalachia. So sit back and enjoy the scenery (make sure you fuel up before you head into the countryside, though!).

Biltmore Estate

: If you arrive in Asheville with some time to spare, spend the afternoon visiting Biltmore Estate. Built by George Vanderbilt, it’s America’s largest home and rests on a beautiful 8,000-acre estate in Asheville’s Blue Ridge Mountains.

Pisgah National Forest

: Drive about 45 minutes into this forest to the Looking Glass Rock trailhead. The trail is 5.8 miles out and back at a gentle climb. And when you reach the top, you’ll be rewarded with a magnificent vista of the Appalachian mountains. It’s dog friendly, too!

Where to eat in Asheville

Twisted Laurel

($$): For a filling dinner after a long day, this is a great option for Mediterranean food. It’s a charming cafe that offers healthy meals and an extensive cocktail list. Their lasagna is an ideal treat after a long day of walking!

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Food trail road trips

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On the road: Asheville to Myrtle Beach

307 miles, 5 hours

After a long day of hiking, relax on a slightly longer car ride that cuts from mountain scenery to the Atlantic Ocean. Enjoy some beautiful views and interesting landscapes along the way.

After leaving Asheville, follow the I-26 E and take exit 170. Take State Rd S-21-24, US-76 E and US-501 S to US-17 BUS N until you reach Myrtle Beach!

Where to eat from Asheville to Myrtle Beach

Early Girl Eatery

($$-$$$): Check out this farm-to-table southern-style spot in Asheville for a hearty breakfast before you hit the road.

Real Mexico Restaurant y Tienda

($): Stop in Columbia, South Carolina for some delicious, authentic food. We recommend trying their birria tacos with the consomme!

Hook and Barrel

($$-$$$): There are a few good options for dinner in Myrtle Beach, but Hook and Barrel’s fresh seafood and hip atmosphere shouldn’t be missed!

What to do from Asheville to Myrtle Beach

Chimney Rock

: Set off from Asheville early, stopping at this nature lover’s paradise for dramatic views and mountain air.

A day on Myrtle Beach

Myrtle Beach is full of attractions, home to 14 distinct communities and 60 miles of sand along the Atlantic Ocean. But after a long journey, nothing is better than soaking up some rays and enjoying local cuisine.

Where to stay in Myrtle Beach

Westgate Myrtle Beach Oceanfront Resort

: Myrtle Beach is home to a number of good hotels at different price points. For an affordable but luxurious stay, try this beautiful, all-service resort overlooking the ocean. Cost per night: from $119.

Where to eat in Myrtle Beach

Croissants Bistro

($$): Head to this Myrtle Beach staple for breakfast. Try the avocado toast and one of their many extensive coffee options.

River City Cafe

($$-$$): For lunch, look into River City Cafe. They offer a wide range of food options in cool, seaside-themed digs. Their burgers are a Myrtle Beach staple, but give the Mahi sandwich a go.

Banditos

($$): Finish your day with yummy Mexican food at this pint-sized, oceanfront restaurant. The tacos are a must, accompanied by any of a number of their specialty margaritas.

What to do in Myrtle Beach

Beach day!: Bring your swimming gear, beach towels, and sunscreen—a day at the beach is a perfect way to cap off the trip. If you’re inclined to give something else a go, check out any number of old-fashioned arcades along the beachfront.

SkyWheel

: You can also cap off your evening with a ride on the SkyWheel, which rises almost 200 feet into the night sky and provides incomparable views of the beach.

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Road trip games

Why you need roadside assistance

Unfortunately, breakdowns happen. Whether you run out of gas, collide with another car, or pop a tire, it’s possible that you might need help to keep your road trip going.

For those situations,

Jerry

has a great roadside assistance package. It features up to 10 miles of towing plus jump starts, tire changes, fuel deliveries, and more.

The package also comes with some exclusive benefits, including car advice, key replacement, and Uber credits. And it only costs $6.99 for one car!

The fast route back

The speediest way to Chicago is to effectively go back the way you came—but a bit more directly. Head up through North Carolina, Tennessee, Kentucky, and Indiana before arriving back in the Windy City.

Without an overnight stop, the journey will likely take you 12 hours. But if you fancy breaking it up, stay for a night in Lexington, about halfway to Chi-Town.

The scenic route back

If you’re pining for more mountain scenery—as well as another city to check out—you can extend the trip by three days.

Set off by heading northeast towards Virginia, getting on the famous Blue Ridge Parkway in Grayson County. Take the BRP north, stopping at Grayson Highlands State Park to stretch your legs. Get off the BRP at i-85, driving northeast to Roanoke, where you can stay for the night.

The next morning, drive five hours to Cincinnati and explore the Over-the-Rhine district for interesting architecture and a variety of food. You can also catch a ballgame at Great American Ballpark.

21c Museum Hotel is a good resting point for the evening—and a final stop before finishing the six-hour journey to Chicago.

Key Takeaway An extra couple of days will allow you to explore more mountain scenery, as well as another exciting midwestern city.

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What can give me peace of mind on a 1,000-mile road trip?

Finding great roadside assistance

No matter where you’re going or for how long you’re traveling, you’ll want excellent roadside assistance coverage. No one enjoys getting stuck on the side of the road with a flat!

For the best rate and coverage, try

Jerry

. Jerry’s roadside assistance includes tons of amazing features and benefits that will keep you safe and offer peace of mind during your trip:

Vehicle towing up to 10 miles

Jumpstarts

Tire changes

Lockout services

Fuel delivery

Winching

Roadside reimbursement

Rental vehicle roadside reimbursement

Your exclusive member benefits include Uber credits, key replacement, tire repair, and so much more. And it all starts at just $6.99 for one car!

"I’m saving money! I received a quote of half of what I was paying and added stuff like roadside assistance. I paid for 6 months upfront and it made it even cheaper! I’m blown away at how easy the process was and now my insurance is paid for 6 months. I’ve never been able to do that before and I have the same coverage—I’m so glad I gave this a try!" —Jerry user

FAQs

Are there any must-try foods on my road trip?

Yes! We’ve covered some classics, but there are some local specials, too.

When you’re in Louisville, tuck into a Hot Brown, a warm, open-faced sandwich loaded with turkey and cheese. Otherwise, enjoy as many southern side dishes as you can—mac n cheese, baked beans, and collard greens are always good bets.

What happens if I break down?

It’s possible your car could malfunction, but you can take several steps to ensure that you’re as safe as possible. Get your car serviced on time, keep refilling your gas tank, and check your tire pressure before you leave. Most importantly, purchase the best, most affordable insurance—and sign up for Jerry’s roadside assistance program so you’re always covered!

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