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$134+ Cheap flights from Winnipeg (YWG) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Winnipeg to Chicago are usually found in June or March, booked 71 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Winnipeg to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

January

Cheapest in

June

Round-trip from

$261
(Kiwi.com)

One-way from

$134
(Kiwi.com)
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
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High demand for flights, 16% potential price rise
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Best time to find cheap flights, 11% potential price drop
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From Winnipeg to Chicago (CHI)
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One-way flight from Winnipeg to Chicago (CHI)
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Find flight deals from Winnipeg to Chicago

Cheapest flights from Winnipeg to Chicago
Explore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:30 amYWG - ORD
2 stops17h 03mMultiple Airlines
Thu 12/126:33 pmORD - YWG
2 stops20h 37mMultiple Airlines
Deal found 11/20$358
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:30 amYWG - MDW
1 stop9h 42mMultiple Airlines
Thu 12/1211:25 amMDW - YWG
2 stops9h 44mMultiple Airlines
Deal found 11/20$402
This Air Canada deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/147:30 amYWG - ORD
1 stop7h 21mAir Canada
Wed 12/187:19 amORD - YWG
1 stop6h 39mAir Canada
Deal found 11/20$404
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/182:15 pmYWG - ORD
Nonstop2h 30mUnited Airlines
Wed 12/2512:56 pmORD - YWG
Nonstop2h 32mUnited Airlines
Deal found 11/19$430
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/186:55 amYWG - MDW
1 stop6h 36mDelta
Wed 12/254:50 pmMDW - YWG
1 stop6h 53mDelta
Deal found 11/19$470
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1312:35 pmYWG - ORD
1 stop7h 15mDelta
Tue 12/171:45 pmORD - YWG
2 stops9h 49mDelta
Deal found 11/20$472
This KAYAK deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:00 amYWG - ORD
2 stops14h 29mWestJet
Tue 12/176:20 amORD - YWG
1 stop5h 25mWestJet
Deal found 11/20$522
This Orbitz deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:00 amYWG - MDW
2 stops17h 06mWestJet
Tue 12/1712:44 pmMDW - YWG
2 stops11h 51mWestJet
Deal found 11/20$536
This Porter Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1311:35 amYWG - MDW
2 stops24h 25mPorter Airlines
Tue 12/1711:15 amMDW - YWG
2 stops30h 49mPorter Airlines
Deal found 11/20$541
This Aeromexico deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/68:00 pmYWG - ORD
2 stops27h 14mAeromexico
Sun 12/81:00 amORD - YWG
2 stops34h 25mAeromexico
Deal found 11/20$2,169

Find flights from Winnipeg to Chicago within your budget

Customize your flight search to find flights from Winnipeg to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 1/7

7:30 am-4:14 pm

1 stop8h 44m

Chicago Midway

Mon 1/13

6:15 am-3:10 pm

1 stop8h 55m

$261

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/6

7:30 am-12:33 am

2 stops17h 03m

Chicago O'Hare Intl

Thu 12/12

6:33 pm-3:10 pm

2 stops20h 37m

$358

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 3/13

8:15 am-3:56 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 3/17

4:45 pm-12:44 am

1 stop7h 59m

$390

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 12/14

7:30 am-2:51 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 12/18

7:19 am-1:58 pm

1 stop6h 39m

$404

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/14

2:15 pm-4:51 pm

Nonstop2h 36m

Chicago O'Hare Intl

Sun 2/16

9:50 am-5:18 pm

1 stop7h 28m

$427

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/10

6:55 am-6:14 pm

2 stops11h 19m

Chicago Midway

Sun 1/12

9:34 am-4:47 pm

2 stops7h 13m

$428

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/7

5:37 pm-9:58 pm

1 stop4h 21m

Chicago O'Hare Intl

Sun 1/12

6:55 am-4:47 pm

2 stops9h 52m

$428

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 1/7

5:37 pm-12:46 pm

1 stop19h 09m

Chicago Midway

Wed 1/15

10:19 am-4:47 pm

1 stop6h 28m

$484

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 12/13

11:35 am-12:00 pm

2 stops24h 25m

Chicago Midway

Tue 12/17

11:15 am-6:04 pm

2 stops30h 49m

$541

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 12/9

7:30 am-11:42 am

1 stop28h 12m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 18 results
1
2

Compare providers for flights from Winnipeg to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Winnipeg to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Winnipeg to Chicago

Get recent, data-driven insights about flights from Winnipeg to Chicago including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Winnipeg to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Chicago. Price data was last updated on November 15, 2024.

The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Winnipeg to Chicago?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $232). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to CHI?

Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 4% on your trip compared to booking a flight at noon.

Weekly flight availability from Winnipeg to Chicago

Explore weekly flight availability from Winnipeg to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 21, 2024.

The most flights from YWG to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated November 21, 2024.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as WestJet, Air Canada and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,758 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.8
Good
286 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
9,172 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,810 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,238 reviews
Delta
8.0
Very good
8,758 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Chicago?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago. On average, Winnipeg has 3 outbound flights to Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Winnipeg to Chicago round-trip?

    Our cheapest airline available from Winnipeg to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $390 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $404 and $427 round-trip. Users have found that WestJet is 17% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Winnipeg to Chicago one-way?

    The cheapest airline one-way is Porter Airlines, with whom users have recently found tickets for as low as $223. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Winnipeg to Chicago for a low price.

  • What are the most reliable airlines from Winnipeg to Chicago?

    No one likes to see their flight delayed. When booking a flight from Winnipeg to Chicago consider choosing SkyWest Airlines (87%), United Airlines (87%) or Air Canada (87%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Winnipeg to Chicago?

    While on average a flight from Winnipeg to Chicago is generally $621, our data shows the cheapest flight currently is $209. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $227 for that flight.

  • Can I find deals for flights from Winnipeg to Chicago that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Chicago.

  • Can I find deals for business class flights from Winnipeg to Chicago?

    Yes. Cheapflights offers flight deals from Winnipeg to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $232). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Winnipeg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to O'Hare Intl flights
Winnipeg to Midway flights
Winnipeg to St. Louis flights

Top 3 airlines flying from Winnipeg to Chicago

Discover the top 3 airlines that operate flights from Winnipeg to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$289Average$550FlexibilityNo cancel feeOn-time67%
DeltaCheapest$370Average$671FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$441Average$533FlexibilityNo cancel feeOn-time69%
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