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A spacious airport terminal with high ceilings, check-in counters, and a Starbucks coffee shop.

￥32,040 Cheap Flights from Winnipeg (YWG) to Chicago (ORD)

Photo by by O'Hare Intl Airport
Open Photo by by O'Hare Intl Airport

Cheap Flights from Winnipeg to Chicago (YWG-ORD)

Prices were available within the past 7 days and start at ￥32,040 for one-way flights and ￥68,150 for roundtrip, for the period specified. Prices and availability are subject to change.
WestJet
Mon, Sep 14 - Thu, Sep 17
YWG
Winnipeg
ORD
Chicago
￥68,150
Roundtrip
Found 11 hours ago
Select WestJet flight, departing Mon, Sep 14 from Winnipeg to Chicago, returning Thu, Sep 17, priced at ￥68,150 Found 11 hours ago
WestJet
Sat, Aug 29 - Sun, Sep 13
YWG
Winnipeg
ORD
Chicago
￥69,720
Roundtrip
Found 11 hours ago
Select WestJet flight, departing Sat, Aug 29 from Winnipeg to Chicago, returning Sun, Sep 13, priced at ￥69,720 Found 11 hours ago
American Airlines
Wed, Sep 16 - Tue, Sep 22
YWG
Winnipeg
ORD
Chicago
￥75,110
Roundtrip
Found 11 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Winnipeg to Chicago, returning Tue, Sep 22, priced at ￥75,110 Found 11 hours ago
WestJet
Mon, Sep 28 - Fri, Oct 16
YWG
Winnipeg
ORD
Chicago
￥77,070
Roundtrip
Found 11 hours ago
Select WestJet flight, departing Mon, Sep 28 from Winnipeg to Chicago, returning Fri, Oct 16, priced at ￥77,070 Found 11 hours ago
American Airlines
Wed, Sep 16 - Sun, Sep 20
YWG
Winnipeg
ORD
Chicago
￥79,030
Roundtrip
Found 11 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Winnipeg to Chicago, returning Sun, Sep 20, priced at ￥79,030 Found 11 hours ago
American Airlines
Wed, Sep 23 - Wed, Oct 7
YWG
Winnipeg
ORD
Chicago
￥79,830
Roundtrip
Found 11 hours ago
Select American Airlines flight, departing Wed, Sep 23 from Winnipeg to Chicago, returning Wed, Oct 7, priced at ￥79,830 Found 11 hours ago
American Airlines
Fri, Aug 14 - Sun, Aug 16
YWG
Winnipeg
ORD
Chicago
￥80,336
Roundtrip
Found 5 days ago
Select American Airlines flight, departing Fri, Aug 14 from Winnipeg to Chicago, returning Sun, Aug 16, priced at ￥80,336 Found 5 days ago
Air Canada
Wed, Sep 16 - Sat, Sep 19
YWG
Winnipeg
ORD
Chicago
￥91,560
Roundtrip
Found 11 hours ago
Select Air Canada flight, departing Wed, Sep 16 from Winnipeg to Chicago, returning Sat, Sep 19, priced at ￥91,560 Found 11 hours ago
United
Sat, Aug 22 - Sun, Sep 6
YWG
Winnipeg
ORD
Chicago
￥108,680
Roundtrip
Found 11 hours ago
Select United flight, departing Sat, Aug 22 from Winnipeg to Chicago, returning Sun, Sep 6, priced at ￥108,680 Found 11 hours ago
Delta
Wed, Aug 12 - Sun, Aug 23
YWG
Winnipeg
ORD
Chicago
￥112,420
Roundtrip
Found 11 hours ago
Select Delta flight, departing Wed, Aug 12 from Winnipeg to Chicago, returning Sun, Aug 23, priced at ￥112,420 Found 11 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from ￥114,210
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from ￥114,210

Find the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD)

March is typically the cheapest month to fly

From ￥38,898 - ￥95,114 per traveler.

Travel information

Origin airport
Winnipeg James Armstrong Richardson Intl. Airport
Destination airport
Chicago O'Hare Intl. Airport
Distance
1,136 km away
Airlines serving
WestJet, PD, Delta, Air Canada, American Airlines, United
Popular airline
WestJet
Roundtrip price
￥68,150
Average flight time
2 hours 34 mins
*Available to One Key members.