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  • Writer's pictureChristina Trotter

The Ultimate Road Trip on Interstate 55: Drive Chicago to New Orleans

Interstate 55, commonly known as I-55, is a major highway that stretches from the vibrant city of New Orleans, Louisiana on the Gulf of Mexico, to the bustling metropolis of Chicago, Illinois on Lake Michigan. Spanning over 960 miles, this iconic route passes through several states, each offering its unique blend of history, culture, and attractions.

One of my favorite things about road trips is seeing how the country is connected by highways that crisscross the nation. As you get into a large city, often you will come across an interchange of another major highway.

Traveling anytime soon on I-10? Here's my article on Things to Do on an I-10 Roadtrip

We drive from Dallas to Chicago often because that is where my sister and her family lives and we always drive into Chicago on I-55 after connecting onto it in St. Louis.

Alas, we are not headed to Chicago today, but just crossing from Dallas to Smoky Mountain National Park via I-55 in Memphis before connecting onto I-40 to Nashville.

Ah, Memphis. Easily one of my favorite cities. I-55, in fact, has a lot of great cities along its path and is a great road trip. Let me explain…

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I-55 History

Interstate 55 holds a significant place in America's transportation history. Its origins can be traced back to the Federal-Aid Highway Act of 1956, which aimed to develop a comprehensive network of interstate highways across the nation. Construction on I-55 began in the late 1950s and continued through the 1970s, connecting various regions and boosting economic growth. Today, I-55 stands as a testament to the nation's commitment to modernizing its transportation infrastructure.

But why do I love it? Because it starts and ends in 2 of my favorite cities (New Orleans and Chicago) and has some cool cities in between, like Memphis, Jackson, and St. Louis!

Map of Interstate 55 (I-55)

States Traveled Through on I-55: 5

I-55 takes travelers through six states:

  • Louisiana

  • Mississippi

  • Tennessee

  • Arkansas

  • Missouri

  • Illinois

Major Cities along I-55:

  • LaPlace, Louisiana

  • New Orleans (Ok, so it's technically 29 miles off of it)

  • Jackson, Mississippi

  • Memphis,

  • St. Louis

  • Springfield, Illinois

  • Bloomington, Illinois

  • Chicago

Major Attractions / Things to Do Along I-55

La Place and New Orleans, Louisiana

If you've read any of my articles before, I have made it well-known that I love New Orleans. Why? There are many reasons, such as the amazing people, excellent food, intriguing history, celebrations, music, and paranormal activity.

There so many things to do, but some of my favorite things are to:

  • Eat chargrilled oysters at Felix's and generally eat my way through the city

  • Take a riverboat ride on the Mississippi River

  • Visit the World War II Museum (it's amazing - make sure to spend at least half a day there

  • Watch a show at Preservation Hall

Trying to see a lot in one visit? Use my Go City tool to decide if it will save you money to buy a Go City Pass!


Like New Orleans, Memphis is one of my favorite cities to visit. I love Memphis barbecue and enjoy the music and general vibe of the city. Make sure to visit Beale Street and don't leave without visiting Stax or Sun Studios!

  • Memphis Pyramid

  • Beale Street

  • Graceland Memphis

  • The Peabody

  • Civil Rights Museum

  • Sun Studios

  • Stax Studios

Jackson, Mississippi

  • Mississippi Civil Rights Museum

  • Mississippi State Capitol

  • Mississippi Museum of Natural Science Jackson, MS

  • Mississippi Blues Trail Sites

  • Mississippi Writer's Trail Sites

  • Mississippi Civil Rights Trail

Visiting State Capitols is one of many things that I call Super Bucket List items. Learn more and add some to your bucket list. Here's how I suggest you create and manage your bucket list.

St. Louis

  • Gateway Arch & Museum St Louis, MO

  • City Museum St Louis, MO

  • Budweiser Brewery St Louis, MO

Springfield, Illinois

  • Lincoln Home National Historic Site Springfield


My sister and her family live in Chicago so we go at least twice a year, if not more. I also spent many years working in Chicago. It is definitely one of my favorite cities in the United States. There's so many things to do, but if you had limited time, do the following:

  • Go to the top of Willis Tower or the John Hancock (my rec: John Hancock because there are less people, a great view and its on the Magnificent Mile!)

  • Millenium Park

  • The Art Institute of Chicago Chicago, IL

  • Walk and shop the Magnificent Mile Chicago, IL

  • Take the Architectural Tour

Want more ideas? Here is my list of 35 Epic Things to do in Chicago

Total Mileage from New Orleans to Chicago on I-55:

964 miles

Interesting Facts about I-55

  • It crosses the Mississippi River twice (in St. Louis and in Memphis)

  • It connects the jazz of New Orleans to the blues of Chicago

  • I-55 in New Orleans partly consists of the Manchac Swamp Bridge, a nearly 23-mile causeway, one of the largest viaducts in the world.


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