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$130+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 69 days in advance, depart on a Friday or Thursday and return on a Thursday

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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/57:30 amYWG - ORD
1 stop28h 24mMultiple Airlines
Sun 12/710:24 amORD - YWG
2 stops14h 17mMultiple Airlines
Deal found 10/29$198
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/267:30 amYWG - ORD
1 stop16h 38mMultiple Airlines
Wed 12/38:00 amORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 10/29$213
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/49:00 pmYWG - MDW
2 stops25h 12mMultiple Airlines
Sun 12/76:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 10/29$214
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 11/119:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
Tue 11/181:56 pmMDW - YWG
1 stop25h 11mMultiple Airlines
Deal found 10/29$215
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 11/119:00 pmYWG - ORD
2 stops14h 14mMultiple Airlines
Tue 11/1812:37 pmORD - YWG
1 stop26h 30mMultiple Airlines
Deal found 10/29$215
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/49:00 pmYWG - ORD
2 stops17h 40mMultiple Airlines
Sun 12/76:11 amORD - YWG
1 stop8h 56mMultiple Airlines
Deal found 10/29$244
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/287:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
Fri 12/58:42 pmMDW - YWG
2 stops27h 59mMultiple Airlines
Deal found 10/29$274
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 11/159:00 pmYWG - ORD
2 stops13h 38mMultiple Airlines
Sat 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 10/30$282
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/217:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
Tue 11/256:05 amMDW - YWG
2 stops18h 36mMultiple Airlines
Deal found 10/29$285
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/28:00 amYWG - ORD
1 stop15h 06mMultiple Airlines
Thu 12/45:05 amORD - YWG
2 stops19h 36mMultiple Airlines
Deal found 10/29$298
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/217:30 amYWG - ORD
1 stop16h 38mMultiple Airlines
Tue 11/2511:48 amORD - YWG
2 stops27h 19mMultiple Airlines
Deal found 10/29$320
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/217:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
Sun 11/236:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
Deal found 10/30$333

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$198
(Kiwi.com)

One-way from

$130
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$373

Good round-trip deal

$454 or less

Good one-way deal

$225 or less
Provider with most accurate pricing for Winnipeg-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago (CHI) flights.
Search Deals
From Winnipeg to Chicago (CHI)
Search Deals
One-way flight from Winnipeg to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Winnipeg

Fly to

Chicago

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/5

7:30 am-11:54 am

1 stop28h 24m

Chicago O'Hare Intl

Sun 12/7

6:11 am-3:07 pm

1 stop8h 56m

$202

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 11/26

7:30 am-12:08 am

1 stop16h 38m

Chicago O'Hare Intl

Wed 12/3

8:00 am-12:41 am

2 stops16h 41m

$213

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 12/4

9:00 pm-10:12 pm

2 stops25h 12m

Chicago Midway

Sun 12/7

6:15 am-3:07 pm

1 stop8h 52m

$214

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 pm-12:41 pm

2 stops15h 41m

Chicago Midway

Tue 11/18

1:56 pm-3:07 pm

1 stop25h 11m

$215

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 11/28

7:30 am-2:40 pm

1 stop7h 10m

Chicago Midway

Fri 12/5

6:15 am-3:07 pm

1 stop8h 52m

$278

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 11/21

7:30 am-2:40 pm

1 stop7h 10m

Chicago Midway

Tue 11/25

6:05 am-12:41 am

2 stops18h 36m

$285

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 pm-8:27 pm

3 stops23h 27m

Chicago O'Hare Intl

Tue 11/18

10:52 am-6:06 pm

3 stops31h 14m

$290

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 11/21

7:30 am-12:08 am

1 stop16h 38m

Chicago O'Hare Intl

Tue 11/25

11:48 am-3:07 pm

2 stops27h 19m

$320

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 11/21

9:00 pm-11:50 am

2 stops14h 50m

Chicago Midway

Sun 11/23

6:05 am-3:07 pm

1 stop9h 02m

$364

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 pm-12:41 pm

2 stops15h 41m

Chicago Midway

Sun 11/16

6:15 am-3:07 pm

1 stop8h 52m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 36 results
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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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Chicago

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 October 24, 2025.

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 67 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $145). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $397). 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 October 30, 2025.

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 7% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Winnipeg to Chicago?

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 October 30, 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as United Airlines and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,381 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 2 outbound flights to Chicago per day from 1 airline. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What is the cheapest airline to fly from Winnipeg to Chicago round-trip?

    Our cheapest airline available from Winnipeg to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $199 on this airline. Users have found that United Airlines is 54% cheaper than the other options available to this destination.

  • 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 (85%), Air Canada (85%) or United Airlines (85%) 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 $432, our data shows the cheapest flight currently is $207. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $184 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $145). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $397). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 airline flying from Winnipeg to Chicago

Discover the top airline 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 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

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