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Flights from Chicago to Winnipeg

Search for direct flights from Chicago to Winnipeg in the next 3 months. Based on Trip.com's latest 7-day flight data, one-way direct flights start at US$391, and round-trip direct flights start at US$750.

      • Cheapest nonstop
        ORD 09:14
        2h 38m
        Nonstop
        YWG 11:52
        Chicago - Winnipeg | Tue, Jul 21 | United Airlines
        YWG 14:00
        2h 34m
        Nonstop
        ORD 16:34
        Winnipeg - Chicago | Sun, Jul 26 | United Airlines
        US$750 US$1,110
        32% off
        32% off
        US$1,110 US$750
      • ORD 09:14
        2h 38m
        Nonstop
        YWG 11:52
        Chicago - Winnipeg | Wed, Aug 5 | United Airlines
        YWG 07:00
        2h 34m
        Nonstop
        ORD 09:34
        Winnipeg - Chicago | Thu, Aug 6 | United Airlines
        US$777 US$1,110
        30% off
        30% off
        US$1,110 US$777
      • ORD 09:50
        9h 35m
        1 stop
        YWG 19:25
        Chicago - Winnipeg | Mon, Jul 20 | Air Canada
        YWG 09:25
        11h 4m
        1 stop
        ORD 20:29
        Winnipeg - Chicago | Fri, Jul 24 | Flair Airlines
        US$376 US$1,110
        66% off
        66% off
        US$1,110 US$376
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Thu, Aug 20 | WestJet
        YWG 16:55
        23h 45m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Sun, Aug 23 | WestJet
        US$380
        66% off
        US$1,110 US$380
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Mon, Aug 24 | WestJet
        YWG 21:05
        19h 35m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Mon, Aug 31 | WestJet
        US$382
        66% off
        US$1,110 US$382
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Fri, Aug 14 | WestJet
        YWG 07:00
        9h 40m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Fri, Aug 21 | WestJet
        US$390
        65% off
        US$1,110 US$390
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Thu, Sep 10 | WestJet
        YWG 21:05
        19h 35m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Sun, Sep 13 | WestJet
        US$391
        65% off
        US$1,110 US$391
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Mon, Aug 17 | WestJet
        YWG 07:00
        9h 40m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Mon, Aug 24 | WestJet
        US$395
        64% off
        US$1,110 US$395
      • ORD 07:00
        12h 54m
        1 stop
        YWG 19:54
        Chicago - Winnipeg | Wed, Sep 2 | Porter Airlines
        YWG 07:00
        9h 40m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Mon, Sep 7 | WestJet
        US$396
        64% off
        US$1,110 US$396
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Sun, Aug 16 | WestJet
        YWG 07:00
        9h 40m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Sun, Aug 23 | WestJet
        US$396
        64% off
        US$1,110 US$396
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Wed, Aug 19 | WestJet
        YWG 07:00
        9h 40m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Wed, Aug 26 | WestJet
        US$397
        64% off
        US$1,110 US$397
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Fri, Aug 21 | WestJet
        YWG 21:05
        19h 35m
        1 stop
        ORD 16:40
        Winnipeg - Chicago | Fri, Aug 28 | WestJet
        US$399
        64% off
        US$1,110 US$399
      • CHI 13:00
        17h 25m
        1 stop
        YWG 14:00
        Chicago - Winnipeg | Tue, Jul 21 | Normal Airline
        YWG 15:00
        6h
        Nonstop
        CHI 16:00
        Winnipeg - Chicago | Thu, Jul 23 | Normal Airline
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      • Cheapest nonstop
        ORD 20:00
        2h 38m
        Nonstop
        YWG 22:38
        Chicago - Winnipeg | Sun, Aug 9 | United Airlines
        US$391 US$559
        30% off
        30% off
        US$559 US$391
      • ORD 20:00
        2h 38m
        Nonstop
        YWG 22:38
        Chicago - Winnipeg | Sat, Aug 8 | United Airlines
        US$391 US$559
        30% off
        30% off
        US$559 US$391
      • MDW 10:25
        22h
        1 stop
        YWG 08:25
        Chicago - Winnipeg | Tue, Jul 21 | Porter Airlines
        US$160 US$559
        71% off
        71% off
        US$559 US$160
      • ORD 07:25
        25h
        1 stop
        YWG 08:25
        Chicago - Winnipeg | Tue, Jul 21 | Air Canada
        US$164
        71% off
        US$559 US$164
      • ORD 07:25
        25h 15m
        1 stop
        YWG 08:40
        Chicago - Winnipeg | Thu, Sep 3 | Air Canada
        US$180
        68% off
        US$559 US$180
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Mon, Jul 20 | WestJet
        US$189
        66% off
        US$559 US$189
      • MDW 15:20
        18h 25m
        1 stop
        YWG 09:45
        Chicago - Winnipeg | Thu, Jul 30 | Porter Airlines
        US$192
        66% off
        US$559 US$192
      • MDW 10:25
        22h 15m
        1 stop
        YWG 08:40
        Chicago - Winnipeg | Fri, Jul 24 | Porter Airlines
        US$193
        65% off
        US$559 US$193
      • MDW 15:20
        28h 5m
        1 stop
        YWG 19:25
        Chicago - Winnipeg | Thu, Sep 3 | Porter Airlines
        US$193
        65% off
        US$559 US$193
      • ORD 17:30
        7h 25m
        1 stop
        YWG 00:55
        Chicago - Winnipeg | Thu, Aug 20 | WestJet
        US$201
        64% off
        US$559 US$201
      • ORD 07:25
        25h
        1 stop
        YWG 08:25
        Chicago - Winnipeg | Sun, Aug 2 | Air Canada
        US$202
        64% off
        US$559 US$202
      • ORD 14:00
        26h 25m
        1 stop
        YWG 16:25
        Chicago - Winnipeg | Mon, Aug 17 | Air Canada
        US$204
        64% off
        US$559 US$204
      • CHI 13:00
        17h 25m
        1 stop
        YWG 14:00
        Chicago - Winnipeg | Tue, Jul 21 | Normal Airline
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Chicago to Winnipeg Flight Details

The distance between Chicago and Winnipeg is about 1,154.29 km. The average flying time from Chicago to Winnipeg is around 2 hours 31 minutes. Based on Trip.com's latest data, travel demand is highest in July. The off-season for travel is October.

Cheapest one-way flight priceUS$160
Cheapest return ticket priceUS$376
Cheapest monthOctober
Peak season for travelJuly
Flight distance1,154.29 km
Average flight time2 hours 31 minutes
Flight statistics for the Chicago–Winnipeg route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • What are the cheapest flights from Chicago to Winnipeg (CHI-YWG)?

    Based on Trip.com data, Porter Airlines offers one-way fares as low as US$160 on Cheapest nonstop routes (e.g. MDW to YWG on Tue, Jul 21), while Air Canada offers Cheapest nonstop round-trips from US$376 departing on Mon, Jul 20 and returning on Fri, Jul 24.
  • It takes about 2 hours 31 minutes to fly from Chicago to Winnipeg.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Winnipeg is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Chicago to Winnipeg, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, Jul 21, with one-way flights priced at just US$160.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Winnipeg travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Winnipeg is October, when demand for travel is lower.
  • After crunching the numbers on our July flight calendar, it's currently cheapest to fly from Chicago to Winnipeg on July 19, 2026 with Air Canada, with prices starting at US$371.
  • The time difference between Winnipeg and Chicago is 0h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Trip.com Airline Insights on Flights from Chicago to Winnipeg

Which airline offers the cheapest direct flights from Chicago to Winnipeg?

Data is based on the average price of all nonstop flights from Chicago to Winnipeg on Trip.com over the past 12 months.

Based on Trip.com’s data from the past 12 months, WestJet provides the lowest-priced direct flights from Chicago to Winnipeg, with fares starting at US$143.

US$17
US$143
US$269
US$395
US$521
WestJet
US$143
WestJet
United Airlines
US$259
United Airlines
Air Canada
US$521
Air Canada

Which airline operates the most flights from Chicago to Winnipeg?

Total flights from Chicago to Winnipeg across all airlines. (Based on Trip.com data from the past month)

Based on Trip.com’s data from the past month, United Airlines/Air Canada/Air New Zealand operates the most frequent flights from Chicago to Winnipeg, with 15 flights per week.

3
7
11
15
United Airlines
15
United Airlines
Air Canada
15
Air Canada
Air New Zealand
15
Air New Zealand
Copa Airlines
8
Copa Airlines
avianca
7
avianca

How many flights fly from Chicago to Winnipeg daily?

The data is based on the flight numbers for each day of the week from Chicago to Winnipeg within the Trip.com database over the past month.

Based on the past month's historical data from Trip.com, the number of flights from Chicago to Winnipeg is the highest on Friday/Saturday and the lowest on Thursday.

40
34
28
22
Highest
31
Mon
32
Tue
32
Wed
28
Thu
40
Fri
40
Sat
36
Sun

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Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.