St Louis to Chicago road trip: Best stops, distance & drive time

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.

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.

Book mobile-friendly tickets here.

Good St Louis experiences include 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 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.

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 11^th and 12^th 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.

Chicago skyline from Grant Park. Photo by David Whitley/ Best3Stops.

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St Louis to Chicago road trip: Best stops, distance & drive time

Planning a St Louis to Chicago road trip itinerary

Our favourite thing to do in Chicago

St Louis to Chicago distance and driving time

St Louis to Chicago road trip attractions: Cahokia Mounds State Historic Site

St Louis to Chicago drive: Springfield

Attractions between St Louis and Chicago: Pontiac

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