Cheap flights from Chicago to Lake Windermere Area from CA $108

View CA $108 flight on Tue, Sep. 9, 2025Opens in a new window

Popular airlines from Chicago to Lake Windermere Area

  • Delta

    Delta

  • WestJet

    WestJet

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • United

    United

  • Air Canada

    Air Canada

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Cheap flights from Chicago (CHI) to Lake Windermere Area (YYC)

Prices were available within the past 7 days and start at CA $108 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Sep. 23 - Wed, Sep. 24
ORD
Chicago
YYC
Calgary
CA $243 Roundtrip, just found
CA $243
Roundtrip
just found
Select United flight, departing Tue, Sep. 23 from Chicago to Calgary, returning Wed, Sep. 24, priced at CA $243 just found
United
Sun, Sep. 21 - Mon, Sep. 22
ORD
Chicago
YYC
Calgary
CA $251 Roundtrip, found 10 hours ago
CA $251
Roundtrip
found 10 hours ago
Select United flight, departing Sun, Sep. 21 from Chicago to Calgary, returning Mon, Sep. 22, priced at CA $251 found 10 hours ago
WestJet
Tue, Sep. 9 - Thu, Sep. 11
ORD
Chicago
YYC
Calgary
CA $275 Roundtrip, found 2 days ago
CA $275
Roundtrip
found 2 days ago
Select WestJet flight, departing Tue, Sep. 9 from Chicago to Calgary, returning Thu, Sep. 11, priced at CA $275 found 2 days ago
American Airlines
Mon, Sep. 15 - Wed, Sep. 24
ORD
Chicago
YYC
Calgary
CA $278 Roundtrip, found 7 hours ago
CA $278
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Sep. 15 from Chicago to Calgary, returning Wed, Sep. 24, priced at CA $278 found 7 hours ago
Air Canada
Mon, Oct. 20 - Thu, Nov. 6
ORD
Chicago
YYC
Calgary
CA $304 Roundtrip, found 3 hours ago
CA $304
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Mon, Oct. 20 from Chicago to Calgary, returning Thu, Nov. 6, priced at CA $304 found 3 hours ago
Delta
Fri, Oct. 10 - Tue, Oct. 28
ORD
Chicago
YYC
Calgary
CA $350 Roundtrip, found 3 hours ago
CA $350
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Oct. 10 from Chicago to Calgary, returning Tue, Oct. 28, priced at CA $350 found 3 hours ago

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

April is typically the cheapest month to fly

From CA $222 - CA $729 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.