Cheap flights from Winnipeg to Historic Route 66 from CA $272

Cheap flights from Winnipeg (YWG) to Historic Route 66 (CHI)

Prices were available within the past 7 days and start at CA $272 for one-way flights and CA $475 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Sep. 19 - Wed, Oct. 1

YWG

Winnipeg

ORD

Chicago

CA $475 Roundtrip, found 6 days ago

CA $475

Roundtrip

found 6 days ago

Select Air Canada flight, departing Fri, Sep. 19 from Winnipeg to Chicago, returning Wed, Oct. 1, priced at CA $475 found 6 days ago

Sat, Sep. 6 - Sat, Sep. 13

YWG

Winnipeg

ORD

Chicago

CA $476 Roundtrip, found 6 hours ago

CA $476

Roundtrip

found 6 hours ago

Select WestJet flight, departing Sat, Sep. 6 from Winnipeg to Chicago, returning Sat, Sep. 13, priced at CA $476 found 6 hours ago

Tue, Sep. 9 - Wed, Sep. 17

YWG

Winnipeg

ORD

Chicago

CA $480 Roundtrip, found 9 hours ago

CA $480

Roundtrip

found 9 hours ago

Select Delta flight, departing Tue, Sep. 9 from Winnipeg to Chicago, returning Wed, Sep. 17, priced at CA $480 found 9 hours ago

Tue, Sep. 23 - Thu, Oct. 2

YWG

Winnipeg

ORD

Chicago

CA $485 Roundtrip, found 5 days ago

CA $485

Roundtrip

found 5 days ago

Select Air Canada flight, departing Tue, Sep. 23 from Winnipeg to Chicago, returning Thu, Oct. 2, priced at CA $485 found 5 days ago

Fri, Sep. 12 - Sun, Sep. 14

YWG

Winnipeg

ORD

Chicago

CA $486 Roundtrip, found 1 hour ago

CA $486

Roundtrip

found 1 hour ago

Select United flight, departing Fri, Sep. 12 from Winnipeg to Chicago, returning Sun, Sep. 14, priced at CA $486 found 1 hour ago

Wed, Sep. 10 - Tue, Sep. 16

YWG

Winnipeg

MDW

Chicago

CA $487 Roundtrip, found 4 days ago

CA $487

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Sep. 10 from Winnipeg to Chicago, returning Tue, Sep. 16, priced at CA $487 found 4 days ago