Flights to Historic Route 66 from Cleveland - ￥6,660

View ￥6,660 flight on Thu, Oct 16, 2025Opens in a new window

Popular airlines from Cleveland to Historic Route 66

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Cheap Flights from Cleveland to Historic Route 66 (CLE-CHI)

Prices were available within the past 7 days and start at ￥6,660 for one-way flights and ￥25,320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 9 - Thu, Aug 14
CLE
Cleveland
TUL
Tulsa
￥25,320 Roundtrip, found 5 days ago
￥25,320
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 9 from Cleveland to Tulsa, returning Thu, Aug 14, priced at ￥25,320 found 5 days ago
American Airlines
Sat, Aug 9 - Thu, Aug 14
CAK
Akron
ORD
Chicago
￥38,000 Roundtrip, found 6 days ago
￥38,000
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug 9 from Akron to Chicago, returning Thu, Aug 14, priced at ￥38,000 found 6 days ago
American Airlines
Sat, Aug 9 - Thu, Aug 14
CLE
Cleveland
TUL
Tulsa
￥38,860 Roundtrip, found 5 days ago
￥38,860
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 9 from Cleveland to Tulsa, returning Thu, Aug 14, priced at ￥38,860 found 5 days ago
American Airlines
Sat, Aug 9 - Thu, Aug 14
CLE
Cleveland
TUL
Tulsa
￥39,510 Roundtrip, found 5 days ago
￥39,510
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 9 from Cleveland to Tulsa, returning Thu, Aug 14, priced at ￥39,510 found 5 days ago
United
Sat, Aug 9 - Thu, Aug 14
CAK
Akron
ORD
Chicago
￥42,340 Roundtrip, found 6 days ago
￥42,340
Roundtrip
found 6 days ago
Select United flight, departing Sat, Aug 9 from Akron to Chicago, returning Thu, Aug 14, priced at ￥42,340 found 6 days ago
Delta
Thu, Aug 14 - Tue, Aug 19
CLE
Cleveland
ABQ
Albuquerque
￥46,770 Roundtrip, found 17 hours ago
￥46,770
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Aug 14 from Cleveland to Albuquerque, returning Tue, Aug 19, priced at ￥46,770 found 17 hours ago

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

June is typically the cheapest month to fly

From ￥11,284 - ￥28,651 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.