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$112+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 Wednesday and return on a Saturday

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 September 15, 2025.

Round-trip from

$195
(Trip.com)

One-way from

$112
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$363

Good round-trip deal

$466 or less

Good one-way deal

$247 or less
From Winnipeg to Chicago (CHI)
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One-way flight from Winnipeg to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Winnipeg to Chicago (CHI).
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Price to beat on a 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 September 15, 2025.

This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/195:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/14$195
This oojo deal was found by Cheapflights users on 9/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Sun 10/195:30 pmORD - YWG
1 stop29h 40mWestJet
Deal found 9/13$204
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/179:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
Wed 10/292:06 pmMDW - YWG
2 stops34h 35mMultiple Airlines
Deal found 9/14$213
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:00 pmYWG - MDW
2 stops21h 39mMultiple Airlines
Thu 11/61:37 pmMDW - YWG
1 stop25h 30mMultiple Airlines
Deal found 9/15$218
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Sun 10/262:20 pmORD - YWG
1 stop10h 21mWestJet
Deal found 9/14$218
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:30 pmYWG - ORD
1 stop23h 13mWestJet
Sat 10/185:30 pmORD - YWG
1 stop18h 11mWestJet
Deal found 9/15$222
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:30 amYWG - MDW
1 stop11h 09mMultiple Airlines
Sun 11/25:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 9/15$231
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/309:00 pmYWG - ORD
1 stop16h 35mMultiple Airlines
Sat 11/16:00 amORD - YWG
2 stops18h 41mMultiple Airlines
Deal found 9/12$240
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/169:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
Sun 10/266:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 9/14$244
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/35:30 pmYWG - ORD
2 stops19h 09mWestJet
Sun 10/55:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/13$246
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:00 pmYWG - ORD
1 stop16h 35mMultiple Airlines
Thu 11/66:06 pmORD - YWG
2 stops30h 36mMultiple Airlines
Deal found 9/15$263
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/178:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Wed 10/297:43 pmORD - YWG
2 stops23h 29mMultiple Airlines
Deal found 9/14$271

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 September 15, 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 10/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-11:10 pm

1 stop29h 40m

$204

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/16

9:05 pm-4:43 pm

1 stop19h 38m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-12:41 am

1 stop10h 21m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/12

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-9:25 pm

2 stops27h 55m

$236

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/11

6:30 pm-4:43 pm

1 stop22h 13m

Chicago O'Hare Intl

Sat 10/18

5:30 pm-11:26 am

2 stops17h 56m

$244

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/3

5:30 pm-12:39 pm

2 stops19h 09m

Chicago O'Hare Intl

Sun 10/5

5:30 pm-9:01 am

1 stop15h 31m

$246

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/26

9:26 pm-12:39 am

2 stops27h 13m

$266

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

4:10 pm-2:57 pm

2 stops22h 47m

Chicago Midway

Sun 11/2

5:20 am-2:07 pm

1 stop8h 47m

$268

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/30

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Thu 11/6

3:18 pm-3:07 pm

1 stop23h 49m

$275

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/9

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/12

6:20 am-12:30 am

2 stops18h 10m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 34 results
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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 September 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 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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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 September 15, 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 31% 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 September 15, 2025.

The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

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 September 15, 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
8,929 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 7 outbound flights to Chicago per day from 2 airlines. 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 8h 13m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 706 mi.

  • What are the cheapest airlines flying 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. An additional option worth looking into is Air Canada, starting at $230. 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 (84%), Avianca (82%) or SkyWest Airlines (77%) 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 $535, our data shows the cheapest flight currently is $189. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $241 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, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 2 airlines flying from Winnipeg to Chicago

Discover the top 2 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 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$487FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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