Cheap flights from Dallas to Historic Route 66

View AU$72 flight on Wed, 10 Sep. 2025Opens in a new window

Popular airlines from Dallas to Historic Route 66

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Cheap Flights from Dallas (DFW) 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
Wed, 10 Sep. - Wed, 17 Sep.
DFW
Dallas
TUL
Tulsa
AU$142 Return, found 3 days ago
AU$142
Return
found 3 days ago
Select American Airlines flight, departing Wed, 10 Sep. from Dallas to Tulsa, returning Wed, 17 Sep., priced at AU$142 found 3 days ago
American Airlines
Sat, 18 Oct. - Sat, 25 Oct.
DFW
Dallas
ORD
Chicago
AU$232 Return, found 1 day ago
AU$232
Return
found 1 day ago
Select American Airlines flight, departing Sat, 18 Oct. from Dallas to Chicago, returning Sat, 25 Oct., priced at AU$232 found 1 day ago
American Airlines
Wed, 10 Sep. - Wed, 17 Sep.
DFW
Dallas
TUL
Tulsa
AU$234 Return, found 3 days ago
AU$234
Return
found 3 days ago
Select American Airlines flight, departing Wed, 10 Sep. from Dallas to Tulsa, returning Wed, 17 Sep., priced at AU$234 found 3 days ago
Delta
Tue, 16 Dec. - Wed, 17 Dec.
DFW
Dallas
STL
St. Louis
AU$299 Return, just found
AU$299
Return
just found
Select Delta flight, departing Tue, 16 Dec. from Dallas to St. Louis, returning Wed, 17 Dec., priced at AU$299 just found
United
Sat, 18 Oct. - Sat, 25 Oct.
DFW
Dallas
ORD
Chicago
AU$340 Return, found 1 day ago
AU$340
Return
found 1 day ago
Select United flight, departing Sat, 18 Oct. from Dallas to Chicago, returning Sat, 25 Oct., priced at AU$340 found 1 day ago
Alaska Airlines
Mon, 18 Aug. - Mon, 25 Aug.
DFW
Dallas
OKC
Oklahoma City
AU$717 Return, found 4 days ago
AU$717
Return
found 4 days ago
Select Alaska Airlines flight, departing Mon, 18 Aug. from Dallas to Oklahoma City, returning Mon, 25 Aug., priced at AU$717 found 4 days ago

Find the cheapest month to fly from Dallas (DFW) to Chicago (ORD)

September is typically the cheapest month to fly

From AU$62 - AU$181 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.