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Flights from Chicago to Winnipeg
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Flights from Chicago to Winnipeg Starting at €73

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD12:58
        2h 30m
        Nonstop
        YWG15:28
        Thu, Mar 27|Chicago - Winnipeg|Air Canada
        €241€268
        10% OFF
        10% OFF
        €268€241

        Choose Air Canada flights from Chicago to Winnipeg. The one-way direct flight with Air Canada departs from O'Hare International Airport on Thu, Mar 27, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €241 including taxes and charges.

      • ORD12:58
        2h 30m
        Nonstop
        YWG15:28
        Thu, Mar 6|Chicago - Winnipeg|Air Canada
        €244€268
        9% OFF
        9% OFF
        €268€244

        Choose Air Canada flights from Chicago to Winnipeg. The one-way direct flight with Air Canada departs from O'Hare International Airport on Thu, Mar 6, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €244 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 6|Chicago - Winnipeg|WestJet
        €73€268
        73% OFF
        73% OFF
        €268€73

        Choose WestJet flights from Chicago to Winnipeg. The one-way connecting flight with WestJet departs from O'Hare International Airport on Thu, Mar 6, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €73 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Mon, Mar 3|Chicago - Winnipeg|WestJet
        €75
        €75

        Choose WestJet flights from Chicago to Winnipeg. The one-way connecting flight with WestJet departs from O'Hare International Airport on Mon, Mar 3, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €75 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Mon, Mar 10|Chicago - Winnipeg|Frontier Airlines
        €76
        €76

        Choose Frontier Airlines flights from Chicago to Winnipeg. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Mar 10, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €76 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 27|Chicago - Winnipeg|WestJet
        €77
        €77

        Choose WestJet flights from Chicago to Winnipeg. The one-way connecting flight with WestJet departs from O'Hare International Airport on Thu, Mar 27, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €77 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 13|Chicago - Winnipeg|WestJet
        €81
        €81

        Choose WestJet flights from Chicago to Winnipeg. The one-way connecting flight with WestJet departs from O'Hare International Airport on Thu, Mar 13, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €81 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Mon, Mar 24|Chicago - Winnipeg|Frontier Airlines
        €93
        €93

        Choose Frontier Airlines flights from Chicago to Winnipeg. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Mar 24, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €93 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Sun, Mar 2|Chicago - Winnipeg|WestJet
        €95
        €95

        Choose WestJet flights from Chicago to Winnipeg. The one-way connecting flight with WestJet departs from O'Hare International Airport on Sun, Mar 2, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €95 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Fri, Mar 7|Chicago - Winnipeg|Frontier Airlines
        €100
        €100

        Choose Frontier Airlines flights from Chicago to Winnipeg. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Fri, Mar 7, arriving at Winnipeg James Armstrong Richardson International Airport. One-way Prices start from €100 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        YWG02:00 pm
        Thu, Feb 27|Chicago - Winnipeg|Air Canada
        Find More Flights
        Find More Flights

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

Chicago to Winnipeg flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. F91596

    Frontier Airlines

    08:20

    ORD

    2.3h

    11:37

    ATL

    S-T-TF-
    Search

  2. WS1361

    WestJet

    14:05

    ATL

    3.4h

    16:28

    YWG

    SMT-T-S

  3. UA764

    United Airlines

    08:53

    ORD

    3.8h

    11:39

    YYC

    SMTWTFS
    Search

  4. WS236

    WestJet

    21:30

    YYC

    2.0h

    00:31

    YWG

    SMTWTF-

  5. AA3606

    American Airlines

    09:50

    ORD

    1.7h

    12:30

    YYZ

    SMTWTFS
    Search

  6. TS7449

    Air Transat

    22:10

    YYZ

    2.8h

    23:55

    YWG

    SMTWTFS

  7. AA3608

    American Airlines

    11:50

    ORD

    1.7h

    14:30

    YYZ

    S--WT-S
    Search

  8. PD437

    Porter Airlines

    15:55

    YYZ

    2.7h

    17:39

    YWG

    SMTWTFS

  9. PD2388

    Porter Airlines

    12:55

    MDW

    1.7h

    15:37

    YTZ

    SMTWTFS
    Search

  10. WS535

    WestJet

    22:30

    YYZ

    2.7h

    00:13

    YWG

    SMTWTFS

  11. PD2388

    Porter Airlines

    12:55

    MDW

    1.7h

    15:37

    YTZ

    SMTWTFS
    Search

  12. PD437

    Porter Airlines

    15:55

    YYZ

    2.7h

    17:39

    YWG

    SMTWTFS

  13. PD2388

    Porter Airlines

    12:55

    MDW

    1.7h

    15:37

    YTZ

    SMTWTFS
    Search

  14. TS7449

    Air Transat

    22:10

    YYZ

    2.8h

    23:55

    YWG

    SMTWTFS

  15. F92144

    Frontier Airlines

    16:28

    MDW

    2.2h

    19:42

    ATL

    -MT--F-
    Search

  16. WS1361

    WestJet

    14:05

    ATL

    3.4h

    16:28

    YWG

    SMT-T-S

  17. WS1575

    WestJet

    16:45

    ORD

    3.9h

    19:36

    YYC

    S--W--S
    Search

  18. WS236

    WestJet

    21:30

    YYC

    2.0h

    00:31

    YWG

    SMTWTF-

  19. F92292

    Frontier Airlines

    16:50

    MDW

    2.2h

    20:04

    ATL

    SM-WT-S
    Search

  20. WS1361

    WestJet

    14:05

    ATL

    3.4h

    16:28

    YWG

    SMT-T-S
Find more flights and airlines

Find the best time to fly from Chicago to Winnipeg

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Chicago to Winnipeg

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
United Airlines logoUnited Airlines

FAQ

  • When are flight tickets from Chicago (CHI) to Winnipeg (YWG) the cheapest?

    Airlines adjust prices for flights from Chicago to Winnipeg based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Winnipeg (YWG) cost?

    According to Trip.com's data, the lowest price is around €422.

  • How long does it take to fly from Chicago (CHI) to Winnipeg (YWG) and what is the distance?

    It takes around 2 hours 34 minutes to fly from Chicago (CHI) to Winnipeg (YWG).

  • What is the transportation method from the main airport to downtown in Winnipeg?

    • The distance from Winnipeg James Armstrong Richardson International Airport to downtown is about 7 km. It takes about 20 minutes by taxi.

  • What are the most popular airlines that fly from Chicago (CHI) to Winnipeg (YWG)?

    Airlines with flights from Chicago (CHI) to Winnipeg (YWG): United Airlines, Air Canada and Air New Zealand.

How to find a cheap flight from Chicago to Winnipeg

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Winnipeg. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Winnipeg

Cheapest nonstop flight price€73
Cheapest round-trip ticket price€327
Off-season for travelMarch
Peak season for travelNovember
Flight distance1,154.29 km
Average flight time2 hours 34 minutes
Popular airlineUnited Airlines

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