Chicago to Dallas Road Trip Itinerary

Chicago – Dallas

Road trip memories come from the stops you make along the way, more so than the destination itself. Every road trip planning begins with researching dozens of optional stops to take in as the adventure begins. From Chicago, Illinois, to Dallas, Texas, we’ve handled the planning. These are the best places to stop and visit.

Monument Circle, Indianapolis, Indiana

A ground view of the Soldiers and Sailors Monument in Indianapolis, Indiana

In the heart of Downtown Indianapolis sits Monument Circle. Bustling with activity almost any day of the week, be sure to plan lunch at a nearby restaurant. Take the time to visit the top observation deck of the Soldiers and Sailors Monument and take in the breathtaking views of the Circle City.

Gasthof Amish Village, Montgomery, Indiana

Amish horse-drawn buggy
Horse-drawn buggy in the Gasthof Amish Village in Montgomery, Indiana – Photo: Katerina Papathanasiou/The Vale Magazine

Described as an “Oasis in the Farmland” of Southern Indiana, there is plenty to do and see in the Gasthof Amish Village. Enjoy locally made Amish food and crafts and the Gasthof Restaurant, serving up delicious meals all day long. If there’s time, book a stay at the Gasthof Amish Village Inn.

Lower Broadway, Nashville, Tennessee

Lower Broadway in Nashville, Tennessee – Photo: Katerina Papathanasiou/The Vale Magazine

Lower Broadway is the entertainment hub of Nashville. The streets are littered with Honky Tonks and live country music at every turn. With retail shops and restaurants, there is no shortage of things to do.

Printer’s Alley, Nashville, Tennessee

Printer’s Alley in Nashville, Tennessee – Photo: Katerina Papathanasiou/The Vale Magazine

Printer’s Alley, another Nash nightlife hot spot, is a must-see for a hearty dose of history and partying. There is much to eat and drink, as the historic alley boasts restaurants, bars, clubs, and print shops that pay tribute to the once flourishing publishing industry.

The Parthenon, Nashville, Tennessee

The Parthenon in Nashville, Tennessee – Photo: Katerina Papathanasiou/The Vale Magazine

Located in Centennial Park, The Parthenon in Nashville is a full-scale replica of the original, located in Athens, Greece. At its core, the Parthenon is a tribute to architecture, and if the opportunity presents itself to see it at night, take it.

Beale Street, Memphis, Tennessee

Beale Street in Memphis, Tennessee – Photo: Katerina Papathanasiou/The Vale Magazine

Beale Street is all about singing the blues, so expect to hear plenty of live music on this Mississippi river-side historic road. Rich with history, restaurants, and nightlife, Beale Street (Home of the Blues) is knee-deep in blues culture. It’s a Southern road trip staple.

Graceland, Memphis, Tennessee

Graceland, the Home of Elvis Presley
Graceland, the Home of Elvis Presley in Memphis, Tennessee – Photo: Katerina Papathanasiou/The Vale Magazine

Now owned by Lisa Marie Presley, Graceland is the famous estate owned by the late singer, Elvis Presley. Graceland is beautiful, and the perfect stop for anyone who has an interest in music. There is much to do, so maybe plan on an extra day.

The Lorraine Motel, Memphis, Tennessee

the Lorraine Motel in Memphis, Tennessee
The Lorraine Motel, now known as the National Civil Rights Museum, where Martin Luther King Jr. was assassinated – Photo: Katerina Papathanasiou/The Vale Magazine

The National Civil Rights Museum at The Lorraine Motel is a complex of buildings and museums in Memphis that follow the Civil Rights Movement’s timeline, dating back to the 17th century. Newly renovated, The Lorraine Motel is rich with cultural history.

Petit Jean State Park, Conway County, Arkansas

Petit Jean State Park, Conway County, Arkansas – Photo: John W. Iwanski/Flickr

Over 3,000 acres on Conway County, Arkansas, makes up Petit Jean State Park. From overlooks and hiking to waterfalls and mountain views, even the most experienced road-tripper could lose themselves in this park for days. Cabin rentals are available, and there is a restaurant on site.

Ouachita National Forest, Hot Springs, Arkansas

Ouachita National Forest overlooking Hot Springs, Arkansas – Photo: Images By Lane/Flickr

Make it a point to stop off at Ouachita National Forest for a day or two to take in the bike and hiking trails, camping areas, and the beautiful scenery the forest provides. Spend the day fishing, or bring a book and relax next to Cedar Lake.

Hot Springs, Arkansas

Bill Clinton’s boyhood home in Hot Springs, Arkansas – Photo: Katerina Papathanasiou/The Vale Magazine

In addition to Ouachita National Forest, there is a ton to see in Hot Springs. Mountain Tower allows visitors to ascend to the top, taking in breathtaking Hot Springs and beyond. Bill Clinton’s boyhood home is a fun stop, as are Bathhouse Row and the Garvan Woodland Gardens.