Cheap flights from St. Louis to Historic Route 66

View AU$106 flight on Sat, 6 Sep. 2025Opens in a new window

Popular airlines from St. Louis to Historic Route 66

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

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Cheap Flights from St. Louis (STL) to Historic Route 66 (CHI)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 6 Sep. - Sat, 13 Sep.
STL
St. Louis
ORD
Chicago
AU$141 Return, found 1 day ago
AU$141
Return
found 1 day ago
Select American Airlines flight, departing Sat, 6 Sep. from St. Louis to Chicago, returning Sat, 13 Sep., priced at AU$141 found 1 day ago
United
Sat, 6 Sep. - Sat, 13 Sep.
STL
St. Louis
ORD
Chicago
AU$211 Return, found 1 day ago
AU$211
Return
found 1 day ago
Select United flight, departing Sat, 6 Sep. from St. Louis to Chicago, returning Sat, 13 Sep., priced at AU$211 found 1 day ago
American Airlines
Sat, 6 Sep. - Sat, 13 Sep.
STL
St. Louis
ORD
Chicago
AU$232 Return, found 1 day ago
AU$232
Return
found 1 day ago
Select American Airlines flight, departing Sat, 6 Sep. from St. Louis to Chicago, returning Sat, 13 Sep., priced at AU$232 found 1 day ago
United
Sat, 6 Sep. - Sat, 13 Sep.
STL
St. Louis
ORD
Chicago
AU$242 Return, found 1 day ago
AU$242
Return
found 1 day ago
Select United flight, departing Sat, 6 Sep. from St. Louis to Chicago, returning Sat, 13 Sep., priced at AU$242 found 1 day ago
Delta
Sat, 6 Sep. - Sat, 13 Sep.
STL
St. Louis
MDW
Chicago
AU$272 Return, found 1 day ago
AU$272
Return
found 1 day ago
Select Delta flight, departing Sat, 6 Sep. from St. Louis to Chicago, returning Sat, 13 Sep., priced at AU$272 found 1 day ago
Southern Airways Express
Sun, 3 Aug. - Thu, 7 Aug.
STL
St. Louis
ORD
Chicago
AU$345 Return, found 6 days ago
AU$345
Return
found 6 days ago
Select Southern Airways Express flight, departing Sun, 3 Aug. from St. Louis to Chicago, returning Thu, 7 Aug., priced at AU$345 found 6 days ago

Find the cheapest month to fly from St. Louis (STL) to Chicago (ORD)

September is typically the cheapest month to fly

From AU$131 - AU$402 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.