Cheap flights from Vancouver to Historic Route 66

View AU$277 flight on Sat, 6 Sep. 2025Opens in a new window

Popular airlines from Vancouver to Historic Route 66

  • American Airlines

    American Airlines

  • Air Canada

    Air Canada

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

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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.

Air Canada
Thu, 28 Aug. - Wed, 3 Sep.
YVR
Vancouver
ORD
Chicago
AU$492 Return, found 7 hours ago
AU$492
Return
found 7 hours ago
Select Air Canada flight, departing Thu, 28 Aug. from Vancouver to Chicago, returning Wed, 3 Sep., priced at AU$492 found 7 hours ago
Air Canada
Thu, 28 Aug. - Wed, 3 Sep.
YVR
Vancouver
ORD
Chicago
AU$502 Return, found 7 hours ago
AU$502
Return
found 7 hours ago
Select Air Canada flight, departing Thu, 28 Aug. from Vancouver to Chicago, returning Wed, 3 Sep., priced at AU$502 found 7 hours ago
Alaska Airlines
Thu, 28 Aug. - Wed, 3 Sep.
YVR
Vancouver
ORD
Chicago
AU$512 Return, found 7 hours ago
AU$512
Return
found 7 hours ago
Select Alaska Airlines flight, departing Thu, 28 Aug. from Vancouver to Chicago, returning Wed, 3 Sep., priced at AU$512 found 7 hours ago
United
Sun, 3 Aug. - Mon, 4 Aug.
YVR
Vancouver
ORD
Chicago
AU$526 Return, found 6 days ago
AU$526
Return
found 6 days ago
Select United flight, departing Sun, 3 Aug. from Vancouver to Chicago, returning Mon, 4 Aug., priced at AU$526 found 6 days ago
American Airlines
Fri, 10 Oct. - Wed, 15 Oct.
YVR
Vancouver
ORD
Chicago
AU$527 Return, found 1 day ago
AU$527
Return
found 1 day ago
Select American Airlines flight, departing Fri, 10 Oct. from Vancouver to Chicago, returning Wed, 15 Oct., priced at AU$527 found 1 day ago
Delta
Thu, 28 Aug. - Wed, 3 Sep.
YVR
Vancouver
ORD
Chicago
AU$584 Return, found 7 hours ago
AU$584
Return
found 7 hours ago
Select Delta flight, departing Thu, 28 Aug. from Vancouver to Chicago, returning Wed, 3 Sep., priced at AU$584 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.