The best stops to add to a St Louis to Chicago road trip itinerary are the Cahokia Mounds State Historic Site, the Abraham Lincoln Presidential Library in Springfield and the Route 66 Hall of Fame in Pontiac. By car, the distance from St Louis to Chicago is 299 miles, with a driving time of around 4h27m.
Planning a St Louis to Chicago road trip itinerary
A St Louis to Chicago road trip connects the largest city in Missouri to the unquestioned star of Illinois. It’s also the last leg of Route 66 if coming from west to east.
5 great St Louis experiences to book
- 🌆 Take a small group tour of the Gateway Arch – including tickets to the top.
- 🚢 Combine a visit to the Gateway Arch with a river cruise.
- 📸 At the Museum of Illusions, get reels of cool social media photos.
- 👻 Discover the dark side of St Louis on an evening ghost tour.
- 🍽️ On a food and history walking tour, learn about the flavours and stories of 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 Saint Louis Zoo, the Saint Louis Art Museum and the Missouri History Museum in Forest Park, plus the Pulitzer Arts Foundation and Old Courthouse in the city.
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.
Highly recommended Chicago experiences include an architecture river cruise, a crime and gangsters tour of famous Mob sites and a bike tour of the lakefront neighbourhoods.
Key Chicago attractions such as the Chicago Architecture Center, the Art Institute of Chicago, the Shedd Aquarium and the Griffin Museum of Science and Industry are worth visiting. But save time for smaller delights like the Frank Lloyd Wright architecture and the Tiffany Dome in Preston Bradley Hall.
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.
Five great things to do in Chicago
- 🏙️ Marvel at the skyscrapers – on a Chicago River architecture cruise.
- 🖼️ Take an interiors architecture tour – to see stunning glass art and mosaics.
- 🍕 Taste Chicago’s favourite dishes – on a city favourites food tour.
- 🌆 Visit the Willis Tower observation deck – and see the city from above.
- 🕵️ Discover Chicago’s gangster heritage – on a crime and mob tour.
St Louis to Chicago distance and driving time
By car, the distance from St Louis to Chicago is 299 miles. You can expect an approximate driving time of four hours and 27 minutes. The drive from St Louis to Chicago is almost entirely along the I-55.
The best stops on a St Louis to Chicago road trip are the Cahokia Mounds State Historic Site, the Abraham Lincoln Presidential Library in Springfield and the Route 66 Hall of Fame in Pontiac.
St Louis to Chicago road trip attractions: Cahokia Mounds State Historic Site
Just over the Illinois border, the Cahokia Mounds are thought to be the remains of the largest pre-Columbian city in the US. Cahokia was the centre for the Mississippian Culture, and reached its peak in the 11th and 12th centuries.
The mounds themselves are not especially exciting to look at, but the guided tours and Interpretive Center should give a better idea of the scale and sophistication of a city that left no written records behind.
St Louis to Chicago drive: Springfield
The capital of Illinois is more than a little obsessed with Abraham Lincoln. Springfield plays host to Lincoln’s former law offices and home, and his tomb is in the Oak Ridge Cemetery.
The centrepiece attraction of Springfield, however, is the Abraham Lincoln Presidential Library and Museum. It’s expensively assembled, enormous, reverent and utterly riveting if you’ve got even the slightest interest in Lincoln and the American Civil War.
Attractions between St Louis and Chicago: Pontiac
Those with a thing for American cars will probably fancy a peek at the Pontiac-Oakland Museum, but lovers of road trips will gravitate towards the Route 66 Hall of Fame and Museum.
This museum is a much-loved collection of Route 66 memorabilia, with buses, vans, signs and all matter of little oddities that will help road-trippers stock up on ideas for next time.
More St Louis and Chicago road trips
- Getting to St Louis: The best stops on the Detroit to St Louis drive and Indianapolis to St Louis drive.
- Road trips from St Louis: The best stops on the St Louis to Cleveland drive, St Louis to Columbus drive, St Louis to Philadelphia drive and St Louis to Pittsburgh drive.
- Road trips to Chicago from Indiana: Guides to the Indianapolis to Chicago drive and South Bend to Chicago drive.
- Getting to Chicago from Ohio: What to see on the Cincinnati to Chicago drive, Cleveland to Chicago drive, Columbus to Chicago drive and Toledo to Chicago drive.
- The best stops on the Detroit to Chicago drive and Chicago to Philadelphia drive.
