Plan with Rovo. Drive with your favorite map.
Chicago to St. Louis covers about 297 miles and 4.5 to 5 hours, running southwest on I-55 the entire way through Joliet, Bloomington-Normal, Springfield, and Litchfield before crossing into Missouri.
This is the old Route 66 corridor, and I-55 largely parallels the historic highway, so there are frequent small-town exits if you want to detour. As a straight interstate drive, though, it's a simple one — I-55 south the whole way, with no highway changes needed.
I-55 itself isn't tolled between Chicago and St. Louis, but if your trip starts near O'Hare or the western suburbs, you may pick up a few dollars in tolls getting onto I-55 via I-294 or I-355 before you're clear of the tollway system. Once you're on I-55 proper, it's toll-free the rest of the way.
Plan This Route with Rovo →Not on I-55 itself. Illinois Tollway roads like I-294 and I-355 charge tolls, but those only come into play if you're using them to reach I-55 from the Chicago suburbs — the direct I-55 corridor to St. Louis is free.
Yes — at under 5 hours on a single interstate, it's one of the easier one-day drives in the Midwest.
Leaving before 7am or after 9am avoids the worst of the Stevenson Expressway's morning crush getting out of the city; I-55 south of Joliet runs free of major congestion the rest of the way.