Chicago to San Antonio road trip: Distance, drive time & best stops
The best road trip stops on the Chicago to San Antonio drive are St Louis, Springfield MO and Dallas. The distance from Chicago to San Antonio by car is 1,199 miles, with an 18h10m driving time.
Planning a Chicago to San Antonio road trip itinerary
The Chicago to San Antonio drive is an epic journey from Illinois to Texas.
Our favourite thing to do in Chicago
The Chicago architecture cruise has a phenomenal wow factor, with the boat gliding between some of the world’s most legendary skyscrapers.
We found the commentary matches the views, too. Expect a fascinating run-down of the city’s history – and plenty of surprising detail about the buildings you’re seeing.
Chicago’s skyscrapers, music scene and massive collection of cultural attractions make it arguably the most exciting city in the US to visit.
Highly recommended Chicago experiences include an architecture river cruise, a gangsters and ghosts tour of famous Mob sites and a bike tour of the lakefront neighbourhoods. It’s also worth paying a visit to the Field Museum, the 360 Chicago observation deck at the Hancock Tower and the Chicago Architecture Center.
Recommended Chicago hotels include the Club Quarters Central Loop for astonishingly good value. Also consider the Intercontinental Chicago Magnificent Mile for its amazing, historic pool, and the entertainingly science-themed Hotel EMC2.
San Antonio’s most famous site is the Alamo, a fortified Spanish mission that played host to a critical battle in the Texas Revolution. It’s far from the only historic building in the city, though – the San Fernando Cathedral and San Antonio Missions National Historical Park are both visually impressive. It’s worth taking a guided tour of the missions for better understanding.
Further attractions include San Antonio Zoo, the Sea Life aquarium, the magic show at the Magicians Agency Theater and the Hopscotch Immersive Art Experience.
Other San Antonio experiences worth considering are the haunted ghost bus tour, downtown food tours, hop-on hop-off buses and Segway tours.
Book ahead for San Antonio accommodation deals. But try the Hotel Emma for five star opulence and the Canopy by Hilton for youthful energy on the Riverwalk.
Chicago to San Antonio distance and driving time
By car, the distance from Chicago to San Antonio is 1,199 miles. You can expect a driving time of around 18 hours and 10 minutes. The quickest route is usually via the I-55, I-44, US-69 and I-35.
The best stops to add to a Chicago to San Antonio road trip itinerary are St Louis, Springfield MO and Dallas.
For more suggestions, check out the guides to individual legs of the Chicago to San Antonio road trip.
Chicago to San Antonio road trip attractions: St Louis
St Louis is one of America’s great crossroads cities. The major landmark is the 630ft-tall Gateway Arch, which visitors can go to the top of. Other top attractions include the Cathedral Basilica of St Louis, the Missouri Botanical Garden and Busch Stadium.
Good St Louis experiences include highlight-packed trolley tours, true crime walking tours and small group tours that include going to the top of the St Louis Arch and a Mississippi River cruise.
For St Louis accommodation with personality, try the Last Hotel or the Pennywell.
Chicago to San Antonio drive: Springfield MO
Springfield is the third biggest city in Missouri, and packs an impressive amount in. Top of most visitor’s lists is the Wonders of Wildlife National Museum and Aquarium. The aquarium is the best section, but the rest is a quirky celebration of model animals. It flits from penguins in the Antarctic to elephants on the African savanna.
Other options include the Route 66 Car Museum, the Dickerson Park Zoo, the Mizumoto Japanese Garden and craft beer tours.
For something totally bizarre, head to the Pythian Castle, built in 1913 by an order of knights. You can visit on a history tour or a nighttime ghost tour.
Best stops between Chicago and San Antonio: Dallas, Texas
Dallas has plenty of high quality cultural attractions. These include the Nasher Scupture Center, Pioneer Square and the Perot Museum of Science and Nature.
But for many visitors, the main reason to visit Dallas is the JFK assassination. Yes, you can go up to the Book Depository where Lee Harvey Oswald supposedly took his shot from.
Top Dallas experiences include a JFK Assassination and Museum tour, the GeO-Deck at Reunion Tower and a self-guided scavenger hunt.
Good places to stay in Dallas with a pool include the sassy Kimpton Pittman downtown and the historic Warwick Melrose near Turtle Creek.
How to do the JFK sites in Dallas
The best way to combine the JFK sites in Dallas is a special themed tour. This takes in the JFK Memorial, Dealey Plaza and the Grassy Knoll before heading to Lee Harvey Oswald’s rooming house. It finishes in the Sixth Floor Museum of the Texas Book Depository. On the way, expert guides take you through the assassination facts and theories. Find out more here.
More Chicago road trips
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Lafayette IN to Chicago | Lansing MI to Chicago | Chicago to Lexington KY | Chicago to Lincoln NE | Chicago to Little Rock |Louisville to Chicago | Chicago to Madison WI | Chicago to Memphis | Chicago to Milwaukee | Chicago to Minneapolis | Moline IL to Chicago | Chicago to Nashville | Chicago to New Orleans | New York City to Chicago | Chicago to Niagara Falls.
Chicago to Omaha | Chicago to Peoria IL | Chicago to Pigeon Forge | Chicago to Pittsburgh | Chicago to Philadelphia | Chicago to Richmond VA | Rockford IL to Chicago | Scranton to Chicago | Chicago to Sheboygan | Chicago to Springfield IL | South Bend to Chicago | St Louis to Chicago | Syracuse to Chicago | Toledo to Chicago | Chicago to Tulsa | Chicago to Washington DC | Chicago to Wichita | Chicago to Wisconsin Dells.
More San Antonio road trips
Abilene to San Antonio | Albuquerque to San Antonio | Amarillo to San Antonio | Arlington to San Antonio | Austin to San Antonio | San Antonio to Baton Rouge | Colorado Springs to San Antonio | Dallas to San Antonio | Denver to San Antonio | San Antonio to El Paso | Fort Worth to San Antonio | San Antonio to Galveston | Houston to San Antonio | Katy TX to San Antonio | Las Cruces to San Antonio | Memphis to San Antonio | Nashville to San Antonio | New Orleans to San Antonio | Oklahoma City to San Antonio | Phoenix to San Antonio | San Antonio to Salt Lake City | Tulsa to San Antonio.