Cheap flights from Vancouver to Historic Route 66

View AU$274 flight on Thu, 18 Sep. 2025Opens in a new window

Popular airlines from Vancouver to Historic Route 66

  • WestJet

    WestJet

  • American Airlines

    American Airlines

  • Air Canada

    Air Canada

  • Alaska Airlines

    Alaska Airlines

  • United

    United

  • Delta

    Delta

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Cheap Flights from Vancouver (YVR) 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.
YVR
Vancouver
ORD
Chicago
AU$487 Return, found 7 hours ago
AU$487
Return
found 7 hours ago
Select American Airlines flight, departing Wed, 10 Sep. from Vancouver to Chicago, returning Wed, 17 Sep., priced at AU$487 found 7 hours ago
United
Wed, 10 Sep. - Wed, 17 Sep.
YVR
Vancouver
ORD
Chicago
AU$487 Return, found 7 hours ago
AU$487
Return
found 7 hours ago
Select United flight, departing Wed, 10 Sep. from Vancouver to Chicago, returning Wed, 17 Sep., priced at AU$487 found 7 hours ago
WestJet
Wed, 10 Sep. - Wed, 17 Sep.
YVR
Vancouver
ORD
Chicago
AU$487 Return, found 7 hours ago
AU$487
Return
found 7 hours ago
Select WestJet flight, departing Wed, 10 Sep. from Vancouver to Chicago, returning Wed, 17 Sep., priced at AU$487 found 7 hours ago
United
Wed, 10 Sep. - Wed, 17 Sep.
YVR
Vancouver
ORD
Chicago
AU$487 Return, found 7 hours ago
AU$487
Return
found 7 hours ago
Select United flight, departing Wed, 10 Sep. from Vancouver to Chicago, returning Wed, 17 Sep., priced at AU$487 found 7 hours ago
Air Canada
Thu, 28 Aug. - Wed, 3 Sep.
YVR
Vancouver
ORD
Chicago
AU$492 Return, found 2 days ago
AU$492
Return
found 2 days ago
Select Air Canada flight, departing Thu, 28 Aug. from Vancouver to Chicago, returning Wed, 3 Sep., priced at AU$492 found 2 days ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
YVR
Vancouver
ORD
Chicago
AU$496 Return, found 7 hours ago
AU$496
Return
found 7 hours ago
Select Delta flight, departing Wed, 10 Sep. from Vancouver to Chicago, returning Wed, 17 Sep., priced at AU$496 found 7 hours ago

Find the cheapest month to fly from Vancouver (YVR) to Chicago (ORD)

May is typically the cheapest month to fly

From AU$293 - AU$804 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.