HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$164+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 64 days in advance, depart on a Thursday or Friday and return on a Thursday

Cheap 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 December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/208:00 amYWG - ORD
1 stop30h 53mMultiple Airlines
Tue 1/65:29 pmORD - YWG
2 stops42h 06mMultiple Airlines
Deal found 12/14$669
This Air Canada deal was found by Cheapflights users on 12/14. 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.
Mon 12/292:20 pmYWG - ORD
Nonstop2h 43mAir Canada
Fri 1/29:10 amORD - YWG
Nonstop2h 47mAir Canada
Deal found 12/14$688
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:55 amYWG - ORD
2 stops36h 05mWestJet
Tue 1/68:50 amORD - YWG
1 stop26h 13mWestJet
Deal found 12/14$723
This Air Canada deal was found by Cheapflights users on 12/14. 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 12/202:20 pmYWG - ORD
Nonstop2h 43mAir Canada
Tue 1/63:55 pmORD - YWG
1 stop7h 59mAir Canada
Deal found 12/14$746
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amYWG - MDW
2 stops10h 34mWestJet
Sun 12/2811:48 amMDW - YWG
1 stop5h 07mWestJet
Deal found 12/15$768
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:20 pmYWG - MDW
2 stops23h 38mWestJet
Tue 1/69:50 amMDW - YWG
1 stop25h 13mWestJet
Deal found 12/14$781
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amYWG - ORD
2 stops29h 05mWestJet
Sun 12/286:35 amORD - YWG
1 stop5h 10mWestJet
Deal found 12/15$781
This United Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/292:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Fri 1/23:55 pmORD - YWG
1 stop5h 49mUnited Airlines
Deal found 12/14$820
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Mon 12/294:55 pmYWG - MDW
2 stops27h 00mMultiple Airlines
Fri 1/23:10 pmMDW - YWG
1 stop10h 16mMultiple Airlines
Deal found 12/14$875
This Justfly.com deal was found by Cheapflights users on 12/16. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:45 pmYWG - MDW
1 stop23h 34mWestJet
Mon 12/229:29 amMDW - YWG
2 stops26h 06mWestJet
Deal found 12/16$879
This WestJet deal was found by Cheapflights users on 12/14. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:00 amYWG - MDW
2 stops12h 26mWestJet
Fri 1/26:08 pmMDW - YWG
2 stops30h 27mWestJet
Deal found 12/14$1,002

Find 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$214
(Kiwi.com)

One-way from

$164
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$602

Good round-trip deal

$384 or less

Good one-way deal

$362 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. 9% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 16, 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 1/16

5:05 pm-4:52 pm

1 stop23h 47m

Chicago O'Hare Intl

Sun 1/18

8:41 pm-12:43 am

1 stop28h 02m

$232

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/30

5:05 pm-4:51 pm

1 stop23h 46m

Chicago O'Hare Intl

Mon 3/2

4:42 pm-6:05 pm

2 stops25h 23m

$235

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 1/30

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-12:40 am

1 stop10h 20m

$243

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

5:00 pm-4:43 pm

2 stops23h 43m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-1:00 pm

2 stops19h 30m

$243

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 1/12

9:00 pm-12:08 pm

2 stops15h 08m

Chicago O'Hare Intl

Mon 1/19

7:20 am-6:03 pm

1 stop10h 43m

$245

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/12

9:00 pm-10:34 am

2 stops13h 34m

Chicago Midway

Mon 1/19

12:57 pm-12:43 am

1 stop11h 46m

$263

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 2/19

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Mon 2/23

4:42 pm-6:05 pm

2 stops25h 23m

$275

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/17

5:00 am-9:03 pm

2 stops16h 03m

Chicago O'Hare Intl

Tue 1/20

7:20 am-12:35 am

2 stops17h 15m

$291

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 1/13

5:00 am-11:46 pm

2 stops18h 46m

Chicago O'Hare Intl

Tue 1/20

5:15 am-12:42 am

2 stops19h 27m

$296

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/30

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Fri 2/6

7:30 am-12:46 am

1 stop17h 16m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 31 results
1
2
3
4

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 December.
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 December 12, 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 64 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 January is currently the most expensive (average of $466). 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 December 16, 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 6% on your trip compared to booking a flight at noon.

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 December 16, 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

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
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

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

  • How long is the flight from Winnipeg to Chicago?

    There are many flights that can get you from Winnipeg to Chicago in 7h 20m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 706 mi.

  • 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 Copa Airlines (90%), SkyWest Airlines (84%) or Air Canada (84%) 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 $503, our data shows the cheapest flight currently is $148. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $235 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 January is currently the most expensive (average of $466). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$471FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.