As a part of a hog hunting trip for my husband and his brother we rented a truck and planned a road trip from Chicago, Illinois to Dallas, Texas  with the girls going on to San Antonio and the boys staying closer to Dallas for their hunting trip. In planning for this trip, I developed a multi-state road trip to hit up all the best cities that I could along the way. I am sharing  our Illinois to Texas itinerary here now so you too can enjoy his fun-filled route too.

Day One

Chicago, Illinois

We live here so for us, Chicago was not an official stop but just the starting and ending point for our trip. But for those considering this trip from other areas of the midwest or who would be completing this itinerary starting from Texas, it absolutely would be. Here are our recommended sights if you will be visiting Chicago as a part of your trip.

• Science and Industry Museum
• Shedd Aquarium
• Any of Lake Michigans many great beaches
• High-end shopping on the magnificent mile

For those of you who cannot handle large chunks of driving this itinerary is probably not for you. Actually,in that case  taking on a road trip at all is probably not for you. Need help deciding? Our post about planning your road trip style will probably help.  Once you have determined that this is indeed the trip for you it is approximately a 4.5 hour drive from Chicago to your first stop St. Louis, Missouri.

                     St. Louis, Missouri

Our St. Louis pitstop is to the Gateway Arch. I recommend you book a time to go up online which can be done here. You need to keep a fairly tight schedule on the first day and don’t want to risk having to wait for an open time. This will of course require you to ensure you arrive in St. Louis on time. Parking is located down the block and there is a screening process before you can go up so be sure to account for this in your timing. Touring includes museum exhibits in the base and a short tram ride to the top to see the views. If you have time, I recommend walking around by the water and viewing the iconic riverboats. Plan for at least 1.5 hours here and potentially more as this is the perfect time to grab some lunch.

Our next part of the trek was definitely the longest at 9.5 hours. We made sure we had our hotel booked in Dallas as we knew we would be getting in late and had a few bathroom breaks. Despite this, we were still able to make a pit stop upon arrival to the cupcake ATM at Sprinkles which allowed us to have a tasty treat despite the fact that we were getting into town close to midnight. And when else can you get midnight cupcakes then on vacation?

Day Two

                            Dallas, Texas

They don’t lie when they say everything is bigger in Texas. Everything in Dallas seems so large and pristine. Dallas is also sadly the site of the assassination of President John F. Kennedy.  So start at the Sixth Floor Museum at Dealey Plaza to learn all about this somber event in U.S. History. Then check out the site on the street below  where you will likely find a conspiracy theorist happy to gab your ear off about his personal theories as to who killed JFK. Also nearby is the beautiful John F. Kennedy Memorial Plaza which is worth a visit. If you are a fan of the car repair show Gas Monkey you can check out there location in Dallas and maybe even see them filming. We visited their restaurant of the same name for lunch and enjoyed the food, car decor and view of the ducks and turtles in their pond from the outdoor seating.

                    Fort Worth, Texas

Spend the evening in nearby Fort Worth, Texas at an authentic Texas Rodeo. The Fort Worth Stock Yards provide a truly Texan experience and a great place to dine on some Texas Barbecue.  Be sure and arrive early so you can wander the nearby streets and check out all the shops selling western wear. Then sit down for an evening of rodeo fun.

Day Three

                       San Antonio, Texas

Leaving Dallas for San Antonio is a four hour drive. I recommend leaving right after your breakfast so you can get there before lunch. Once you arrive and settle into your accommodations, start your time with a stroll down the beautiful River Walk pathways. It is a beautiful walk and what should be San Antonio’s  true claim to fame in my opinion.  Lined along it’s paths are tourist shops, restaurants and hotels. This is the perfect time to try a place out for lunch. We tried out a Mexican and an Italian restaurant on the riverwalk, with the river view of course, and enjoyed them both thoroughly. Book a visit to the Alamo in afternoon, San Antonio’s most well-known site. . You will view what left of its’s architecture  and learn more about it’s iconic story in the inner exhibits.  You just can’t visit San Antonio without checking it out at least once. Spend the evening going up the Tower of the Americas. For a price, you can go up the Tower of the Americas in one of the three elevators to the observation deck. Once up there you have the best views of the San Antonio skyline. You can also book to eat dinner at the restaurant they have up there. The tower is located in Hemisfair park which I wish we had more time to better explore as it seems like a fun space in it’s own right. If you time it right you could be up there at sunset and get the daytime and night lights views.

Day Four

Wake up in San Antonio and head to the Missions National Historic Park. These beautiful 1700’s christian missions are remnants of the Spanish attempts to  convert the native community to christianity. It’s a pretty somber story that they explain in a short video in the  visitor center. Given that they pre-date the United States, they are very old in comparison to most sites in America. For our full San Antonio trip  After the Missions it is time to bid San Antonio adieu and head to your next location either an hour and a half to Austin, Texas or the long trek to Memphis , Tennessee 11 hours. If going straight to Memphis you could skip missions,  or spend another full day in San Antonio as we did and go to Memphis the next day. Either way, let your accommodations know to expect a late check-in. 

                           Austin, Texas

Due to limited time, we had to make a choice between San, Antonio and Austin and I ultimately chose San Antonio. While I have no regrets, San Antonio was lovely, Austin also has a lot to offer. If you have extra days for your trip, add a stop in Austin as shown on the map. Only an hour and a half from San Antonio it’s fits perfectly into the itinerary as it heads you in the direction of your next stop, Memphis, Tennessee.

Day Five

                     Memphis, Tennessee

Our number one stop for a trip to Memphis was to visit Graceland, former home of Elvis Presley. You will need to set either your whole morning or whole afternoon for this activity. Graceland was one of my favorite attractions on this road trip. We will continue to remember fondly the extensive Elvis Presley Memorabilia, the in depth look into his home and belongings and the opportunity to visit the final resting place of the King himself. To hear more about Graceland check out our full post here.

After your morning at Graceland head down to Bond Street, home of the blues and great eats, especially Barbeque. The street is worth a wander and great spot to get your lunch. Then find time to see the National Civil Rights Museum which includes the Lorraine Motel, where Martin Luther King was assassinated. Another quick spot to see is the Peabody Hotel which  for 90 years has had ducks march to the lobby fountain at 11 a.m. and 5 p.m. each day.

Day Six

Nashville, Tennessee

From Memphis to Nashville is a three hour drive. So if you just get up and go you can make it to Nashville for lunch and some iconic Spicy Nashville style chicken. You can spend the vast majority of your time on the main drag of Broadway Street. Checking out the bars alone, with their near constant live performances can keep you entertained for many hours.  You can also explore the western style shops and restaurants. We also made time for some Tennessee Whiskey, with a tasting and distillery tour. If you are a big country music fan you can also check out the numerous country music artist museums in the area as well. 

Day Seven

Louisville, Kentucky

From Memphis, Tennessee to  Louisville, Kentucky is a three hour drive. Leave in the morning and book yourself a late morning or early afternoon tour at Kentucky Derby Museum at Churchill Downs. We enjoyed touring the ground of  the location of the Iconic Kentucky Derby and learning more about the races themselves in the museum. I am sure Louisville has even more to offer if you desire to spend more time there, but due to time constraints, this was our only stop. 

Day seven is your final travel day and the end of your epic Illinois to Texas Road Trip Itinerary. You will leave Louisville and  head back to Chicago, a five hour drive. It’s plenty of time to cherish all the great memories you have created on this five state trip, more if you count how many states you drove through. Now get home and cherish all the new memories you have created with your road trip companions and start planning  your next one. There are so many ways in which you can spend more or less time in any given location and we would love to hear what you include in your own Texas to Illinois road trip in the comments below.