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Cheap flight deals from Chicago to Winnipeg Starting at VND 1,947,836

Whether you’re going for a one-way or round-trip to Winnipeg, we’ve got you covered! Check out these different flight options from Chicago below.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD12:58
        2h 30m
        Nonstop
        YWG15:28
        Thu, Mar 27|Chicago - Winnipeg|Air Canada
        VND 6,418,049VND 8,523,165
        25% OFF
        25% OFF
        VND 8,523,165VND 6,418,049

        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 VND 6,418,049 including taxes and charges.

      • ORD12:58
        2h 30m
        Nonstop
        YWG15:28
        Thu, Mar 6|Chicago - Winnipeg|Air Canada
        VND 6,477,605VND 8,523,165
        24% OFF
        24% OFF
        VND 8,523,165VND 6,477,605

        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 VND 6,477,605 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 6|Chicago - Winnipeg|WestJet
        VND 1,947,836VND 8,523,165
        77% OFF
        77% OFF
        VND 8,523,165VND 1,947,836

        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 VND 1,947,836 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Mon, Mar 3|Chicago - Winnipeg|WestJet
        VND 2,000,385
        VND 2,000,385

        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 VND 2,000,385 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Mon, Mar 10|Chicago - Winnipeg|Frontier Airlines
        VND 2,028,412
        VND 2,028,412

        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 VND 2,028,412 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 27|Chicago - Winnipeg|WestJet
        VND 2,052,935
        VND 2,052,935

        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 VND 2,052,935 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Thu, Mar 13|Chicago - Winnipeg|WestJet
        VND 2,165,041
        VND 2,165,041

        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 VND 2,165,041 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Mon, Mar 24|Chicago - Winnipeg|Frontier Airlines
        VND 2,483,841
        VND 2,483,841

        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 VND 2,483,841 including taxes and charges.

      • ORD16:45
        7h 59m
        1 stop
        YWG00:44
        Sun, Mar 2|Chicago - Winnipeg|WestJet
        VND 2,536,391
        VND 2,536,391

        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 VND 2,536,391 including taxes and charges.

      • MDW06:20
        8h 48m
        1 stop
        YWG15:08
        Fri, Mar 7|Chicago - Winnipeg|Frontier Airlines
        VND 2,648,496
        VND 2,648,496

        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 VND 2,648,496 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        YWG02:00 pm
        Wed, Feb 26|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

    08:45

    ORD

    3.9h

    11:41

    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

When is the cheapest time to fly from Chicago to Winnipeg?

Explore the best time to buy affordable tickets to Winnipeg with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

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

Frequently Asked Questions

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

    Airlines adjust prices for flights from Chicago to Winnipeg based on the date and time of your booking. By analyzing data from all airlines, 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 VND 11,221,075.

  • How long does it take to fly from Chicago (CHI) to Winnipeg (YWG)?

    It takes about 2 hours 30 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, by taxi about 20 minutes.

  • 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.

  • What's the most popular airline for non-stop flights from Chicago (CHI) to Winnipeg (YWG)?

    United Airlines operates 1 non-stop flights from Chicago (CHI) to Winnipeg (YWG).

  • How many airports are there in Winnipeg (YWG)?

    There are 1 airport(s) near Winnipeg (YWG): Winnipeg James Armstrong Richardson International Airport.

How to find a cheap flight from Chicago to Winnipeg

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 Info | Chicago to Winnipeg

Cheapest direct flight priceVND 1,947,835
Cheapest return ticket priceVND 8,716,215
Off-season for travelMarch
Peak season for travelNovember
Flight distance1,154.29 km
Average flight time2 hours 30 minutes
Popular airlineUnited Airlines

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