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Flights from Chicago to Winnipeg
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Latest Flight Deals from Chicago to Winnipeg

Book one-way or return flights from Chicago to Winnipeg from as little as NZD 204. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • ORD07:00
        8h 25m
        1 stop
        YWG15:25
        Thu, May 16|Chicago - Winnipeg|Frontier Airlines
        NZD 204NZD 443
        54% OFF
        54% OFF
        NZD 443NZD 204
      • MDW07:00
        8h 25m
        1 stop
        YWG15:25
        Wed, May 1|Chicago - Winnipeg|Frontier Airlines
        NZD 213NZD 443
        52% OFF
        52% OFF
        NZD 443NZD 213
      • MDW07:00
        8h 25m
        1 stop
        YWG15:25
        Wed, May 15|Chicago - Winnipeg|Frontier Airlines
        NZD 217NZD 443
        51% OFF
        51% OFF
        NZD 443NZD 217
      • ORD06:00
        9h 25m
        1 stop
        YWG15:25
        Thu, May 2|Chicago - Winnipeg|Frontier Airlines
        NZD 241
        NZD 241
      • MDW07:27
        7h 58m
        1 stop
        YWG15:25
        Wed, Jun 5|Chicago - Winnipeg|Frontier Airlines
        NZD 258
        NZD 258
      • MDW07:27
        7h 58m
        1 stop
        YWG15:25
        Mon, Jun 10|Chicago - Winnipeg|Frontier Airlines
        NZD 286
        NZD 286
      • MDW07:27
        7h 58m
        1 stop
        YWG15:25
        Mon, Jun 3|Chicago - Winnipeg|Frontier Airlines
        NZD 296
        NZD 296
      • MDW07:27
        7h 55m
        1 stop
        YWG15:22
        Wed, Jul 3|Chicago - Winnipeg|Frontier Airlines
        NZD 301
        NZD 301
      • MDW06:00
        9h 25m
        1 stop
        YWG15:25
        Wed, May 15|Chicago - Winnipeg|WestJet
        NZD 301
        NZD 301
      • ORD12:34
        12h 10m
        1 stop
        YWG00:44
        Mon, May 13|Chicago - Winnipeg|Frontier Airlines
        NZD 307
        NZD 307
      • CHI13:00
        3h 5m
        Direct
        YWG14:00
        Sun, May 5|Chicago - Winnipeg|Frontier Airlines
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Chicago to Winnipeg? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Winnipeg. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to Winnipeg

View airlines operating flights from Chicago to Winnipeg. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From NZD 204
WestJet
From NZD 301
Spirit Airlines
From NZD 308
United Airlines
From NZD 317
Porter Airlines
From NZD 318
Delta Air Lines
From NZD 320
Alaska Airlines
From NZD 352
American Airlines
From NZD 355
Air Canada
From NZD 361
Sun Country Airlines
From NZD 523
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Winnipeg

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Winnipeg.

  • Cheapest
    Frontier Airlines
    ORD
    07:00
    8h 25m
    1 transfer
    YWG
    15:25
    O'Hare International Airport - Winnipeg James Armstrong Richardson International Airport
    Thu, May 16Frontier Airlines
    NZD 204
  • Frontier Airlines
    MDW
    07:00
    8h 25m
    1 transfer
    YWG
    15:25
    Midway International Airport - Winnipeg James Armstrong Richardson International Airport
    Wed, May 1Frontier Airlines
    NZD 213
  • Frontier Airlines
    MDW
    07:00
    8h 25m
    1 transfer
    YWG
    15:25
    Midway International Airport - Winnipeg James Armstrong Richardson International Airport
    Wed, May 1Frontier Airlines
    NZD 213
    Find More Flights

How do I find the cheapest flights?

  • 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 NZD 808.

  • 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 7km. It takes about 20 minutes by taxi.

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

NZD 204

Cheapest round-trip ticket price

NZD 632

Off-season for travel

March

Peak season for travel

October

Flight distance

1,154.29km

Popular airline

United Airlines

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