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Cheap Flights from Winnipeg James Armstrong Richardson International Airport to Chicago

Search for flights from Winnipeg James Armstrong Richardson International Airport to Chicago and check out affordable one-way and round-trip options.

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  • Round-trip
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Selected Airlines from Winnipeg James Armstrong Richardson International Airport to Chicago

See which airlines fly from Winnipeg James Armstrong Richardson International Airport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

WestJet
From CAD 145
Delta Air Lines
From CAD 259
Porter Airlines
From CAD 260
Flair Airlines
From CAD 282
United Airlines
From CAD 293
Air Transat
From CAD 294
Air Canada
From CAD 300

Find more flights and airlines

Find Suitable Airport in Chicago

Learn about different airports in Chicago, find the best flight and transfer options, and plan your journey.

Flight Schedule from Winnipeg James Armstrong Richardson International Airport to Chicago

Check the schedule for flights from Winnipeg James Armstrong Richardson International Airport to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule
  1. WS520

    05:00

    YWG

    2.6h

    08:39

    YYZ

    SMTWTFS
  2. PD2397

    20:50

    YTZ

    1.8h

    21:37

    MDW

    --TWT-S
  3. PD424

    05:00

    YWG

    2.5h

    08:33

    YYZ

    SMTWT-S
  4. PD2393

    15:50

    YTZ

    1.8h

    16:40

    MDW

    SMTWT-S
  5. WS1360

    07:30

    YWG

    3.3h

    11:49

    ATL

    S-TWT-S
  6. F92781

    16:48

    ATL

    1.9h

    17:45

    MDW

    ------S
  7. WS1360

    07:30

    YWG

    3.3h

    11:49

    ATL

    S-TWT-S
  8. F91595

    12:03

    ATL

    2.1h

    13:11

    ORD

    SMT-TF-
  9. WS261

    08:15

    YWG

    2.5h

    09:42

    YYC

    SMTWTFS
  10. WS1588

    12:30

    YYC

    3.6h

    17:09

    ORD

    ---WTFS
  11. F8642

    09:30

    YWG

    2.5h

    13:00

    YYZ

    S-TWTFS
  12. PD2397

    20:50

    YTZ

    1.8h

    21:37

    MDW

    --TWT-S
  13. WS534

    09:30

    YWG

    2.4h

    12:54

    YYZ

    SMTWTFS
  14. PD2397

    20:50

    YTZ

    1.8h

    21:37

    MDW

    --TWT-S
  15. WS534

    09:30

    YWG

    2.4h

    12:54

    YYZ

    SMTWTFS
  16. PD2399

    18:15

    YTZ

    1.8h

    19:02

    MDW

    -----F-
  17. PD420

    10:00

    YWG

    2.5h

    13:31

    YYZ

    S--WTFS
  18. PD2397

    20:50

    YTZ

    1.8h

    21:37

    MDW

    --TWT-S
  19. WS1352

    17:00

    YWG

    3.5h

    18:30

    LAS

    ---W--S
  20. F92146

    22:59

    LAS

    3.8h

    04:47

    ORD

    ---W---

Flight Info of Flights from Winnipeg James Armstrong Richardson International Airport to Chicago

Cheapest return ticket price

CAD 406

Cheapest direct flight price

CAD 145

Off-season travel month

September

Peak season for travel

June

FAQs for Winnipeg James Armstrong Richardson International Airport to Chicago Flights