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Winnipeg

$158+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jun 17 — Jun 241
Wed 6/17
Wed 6/24
1 adult, Economy
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Cheap flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 10/117:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/16$328
This Trip.com deal was found by Cheapflights users on 5/14. 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.
Wed 9/25:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 9/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/14$362
This Trip.com deal was found by Cheapflights users on 5/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 10/104:55 pm
YWG
-
ORD
1 stop23h 45m
WestJet
Deal found 5/16$365
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 6/1610:15 am
MDW
-
YWG
1 stop23h 30m
Multiple Airlines
Mon 6/226:05 pm
YWG
-
MDW
1 stop15h 35m
Multiple Airlines
Deal found 5/13$402
This Trip.com deal was found by Cheapflights users on 5/17. 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 6/45:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 6/79:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 5/17$404
This WestJet deal was found by Cheapflights users on 5/15. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 10/197:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 5/15$405
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Wed 6/1710:15 am
MDW
-
YWG
1 stop23h 30m
Multiple Airlines
Sun 6/218:45 pm
YWG
-
MDW
1 stop12h 55m
Multiple Airlines
Deal found 5/13$408
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 6/1610:15 am
MDW
-
YWG
1 stop9h 34m
Porter Airlines
Sun 6/218:45 pm
YWG
-
MDW
1 stop12h 55m
Porter Airlines
Deal found 5/13$413
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am
ORD
-
YWG
2 stops10h 58m
Multiple Airlines
Sun 10/117:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 5/16$414
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 6/43:20 pm
MDW
-
YWG
1 stop9h 35m
Multiple Airlines
Mon 6/89:05 pm
YWG
-
MDW
2 stops14h 07m
Multiple Airlines
Deal found 5/14$418
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 10/104:55 pm
YWG
-
ORD
2 stops12h 47m
Multiple Airlines
Deal found 5/16$421
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 6/1610:15 am
MDW
-
YWG
1 stop9h 34m
Multiple Airlines
Sat 6/205:10 pm
YWG
-
MDW
1 stop16h 30m
Multiple Airlines
Deal found 5/13$421

Find flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). 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 May 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(Kiwi.com)

One-way from

$158
(Justfly.com)

Popular in

January

Cheapest in

February

Average price

$755

Good round-trip deal

$755 or less

Good one-way deal

$624 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Chicago (CHI) to Winnipeg
Search Deals
One-way flight from Chicago (CHI) to Winnipeg
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($149 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Winnipeg.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Winnipeg 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 May 18, 2026.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 7/17

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 7/19

8:45 pm-9:40 am

1 stop12h 55m

$528

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/27

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Sat 5/30

6:40 am-1:19 pm

1 stop6h 39m

$635

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/20

8:08 am-3:19 pm

1 stop7h 11m

Winnipeg

Tue 6/23

9:20 am-4:18 pm

1 stop6h 58m

$660

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/26

7:16 pm-11:38 am

1 stop16h 22m

Winnipeg

Sat 7/4

7:00 am-5:54 pm

2 stops10h 54m

$701

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 7/17

11:45 am-7:54 pm

1 stop8h 09m

Winnipeg

Mon 7/20

12:15 pm-7:29 pm

1 stop7h 14m

$724

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 7/17

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 7/19

9:05 pm-4:40 pm

1 stop19h 35m

$756

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/28

6:00 am-5:25 pm

2 stops11h 25m

Winnipeg

Sun 5/31

9:05 pm-4:40 pm

1 stop19h 35m

$756

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 10/20

12:30 pm-11:34 pm

1 stop11h 04m

Winnipeg

Sat 10/24

8:00 am-4:50 pm

1 stop8h 50m

$764

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/27

9:49 am-10:10 pm

2 stops12h 21m

Winnipeg

Fri 7/31

6:15 am-6:25 pm

2 stops12h 10m

$778

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/29

9:42 am-7:49 pm

1 stop10h 07m

Winnipeg

Sun 5/31

9:20 am-4:20 pm

1 stop7h 00m

$783

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 41 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Winnipeg

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 Chicago to Winnipeg in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg 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 Chicago-Winnipeg 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 Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago 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 Chicago to Winnipeg

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $62). Flying from Chicago to Winnipeg in January is currently the most expensive (average of $1,074). 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 CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 18, 2026.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 27% on airfare.

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

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated May 18, 2026.
Read reviews from past customers who have flown United Airlines from Chicago to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,737 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,737 reviews
United Airlines
7.4
Good
9,737 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. 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 into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 2 inbound flights from 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 Chicago to Winnipeg?

    A quick flight from Chicago to Winnipeg can take about 7h 11m. Porter Airlines provides one of the quickest options available for as low as $660. There are 706 mi between Chicago and Winnipeg. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $156. Another option worth looking into is United Airlines, starting at $291 round trip. These flights start at 75% lower than the current average price 3 months from now.

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

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (64%), Air Canada (64%) and United Airlines (64%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $381. On average you can expect to pay $855. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $414.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg 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 Chicago to Winnipeg?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $62). Flying from Chicago to Winnipeg in January is currently the most expensive (average of $1,074). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Winnipeg

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

Top 2 airlines flying from Chicago to Winnipeg

Discover the top 2 airlines that operate flights from Chicago to Winnipeg. 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 May 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$291Average$672FlexibilityNo cancel feeOn-time69%

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