Cheap flights from Calgary to Historic Route 66

View AU$191 flight on Tue, 23 Sep. 2025Opens in a new window

Popular airlines from Calgary to Historic Route 66

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Calgary (YYC) 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, 16 Oct. - Thu, 23 Oct.
YYC
Calgary
ORD
Chicago
AU$328 Return, found 3 days ago
AU$328
Return
found 3 days ago
Select Air Canada flight, departing Thu, 16 Oct. from Calgary to Chicago, returning Thu, 23 Oct., priced at AU$328 found 3 days ago
United
Wed, 8 Oct. - Wed, 22 Oct.
YYC
Calgary
ORD
Chicago
AU$337 Return, found 4 days ago
AU$337
Return
found 4 days ago
Select United flight, departing Wed, 8 Oct. from Calgary to Chicago, returning Wed, 22 Oct., priced at AU$337 found 4 days ago
Air Canada
Wed, 1 Oct. - Wed, 8 Oct.
YYC
Calgary
ORD
Chicago
AU$338 Return, found 2 days ago
AU$338
Return
found 2 days ago
Select Air Canada flight, departing Wed, 1 Oct. from Calgary to Chicago, returning Wed, 8 Oct., priced at AU$338 found 2 days ago
WestJet
Thu, 16 Oct. - Thu, 23 Oct.
YYC
Calgary
ORD
Chicago
AU$338 Return, found 3 days ago
AU$338
Return
found 3 days ago
Select WestJet flight, departing Thu, 16 Oct. from Calgary to Chicago, returning Thu, 23 Oct., priced at AU$338 found 3 days ago
Delta
Wed, 1 Oct. - Wed, 8 Oct.
YYC
Calgary
ORD
Chicago
AU$346 Return, found 2 days ago
AU$346
Return
found 2 days ago
Select Delta flight, departing Wed, 1 Oct. from Calgary to Chicago, returning Wed, 8 Oct., priced at AU$346 found 2 days ago
Alaska Airlines
Wed, 1 Oct. - Wed, 8 Oct.
YYC
Calgary
ORD
Chicago
AU$733 Return, found 2 days ago
AU$733
Return
found 2 days ago
Select Alaska Airlines flight, departing Wed, 1 Oct. from Calgary to Chicago, returning Wed, 8 Oct., priced at AU$733 found 2 days ago

Find the cheapest month to fly from Calgary (YYC) to Chicago (ORD)

September is typically the cheapest month to fly

From AU$224 - AU$434 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.