Cheap flights from Cleveland to Historic Route 66

View AU$98 flight on Mon, 17 Nov. 2025Opens in a new window

Popular airlines from Cleveland to Historic Route 66

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

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Cheap Flights from Cleveland (CLE) 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
Thu, 25 Sep. - Sat, 27 Sep.
CLE
Cleveland
ORD
Chicago
AU$196 Return, found 21 hours ago
AU$196
Return
found 21 hours ago
Select American Airlines flight, departing Thu, 25 Sep. from Cleveland to Chicago, returning Sat, 27 Sep., priced at AU$196 found 21 hours ago
American Airlines
Fri, 5 Sep. - Fri, 12 Sep.
CLE
Cleveland
ORD
Chicago
AU$234 Return, found 2 days ago
AU$234
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Sep. from Cleveland to Chicago, returning Fri, 12 Sep., priced at AU$234 found 2 days ago
Delta
Thu, 25 Sep. - Sat, 27 Sep.
CLE
Cleveland
MDW
Chicago
AU$272 Return, found 21 hours ago
AU$272
Return
found 21 hours ago
Select Delta flight, departing Thu, 25 Sep. from Cleveland to Chicago, returning Sat, 27 Sep., priced at AU$272 found 21 hours ago
United
Thu, 25 Sep. - Sat, 27 Sep.
CLE
Cleveland
ORD
Chicago
AU$281 Return, found 21 hours ago
AU$281
Return
found 21 hours ago
Select United flight, departing Thu, 25 Sep. from Cleveland to Chicago, returning Sat, 27 Sep., priced at AU$281 found 21 hours ago
Frontier Airlines
Thu, 9 Oct. - Tue, 14 Oct.
CLE
Cleveland
ORD
Chicago
AU$421 Return, found 6 days ago
AU$421
Return
found 6 days ago
Select Frontier Airlines flight, departing Thu, 9 Oct. from Cleveland to Chicago, returning Tue, 14 Oct., priced at AU$421 found 6 days ago
Spirit Airlines
Thu, 9 Oct. - Sat, 11 Oct.
CLE
Cleveland
ORD
Chicago
AU$422 Return, found 6 days ago
AU$422
Return
found 6 days ago
Select Spirit Airlines flight, departing Thu, 9 Oct. from Cleveland to Chicago, returning Sat, 11 Oct., priced at AU$422 found 6 days ago

Find the cheapest month to fly from Cleveland (CLE) to Chicago (ORD)

June is typically the cheapest month to fly

From AU$118 - AU$300 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.