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$140+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheap 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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$574

Good round-trip deal

$1,004 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
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Find 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 octubre 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.
jue. 12/47:23 pmMDW - YWG
2 stops29h 18mMultiple Airlines
dom. 12/77:30 amYWG - MDW
1 stop26h 22mMultiple Airlines
Deal found 10/29$193
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.
mar. 12/92:49 pmMDW - YWG
1 stop24h 18mMultiple Airlines
vie. 12/127:30 amYWG - MDW
1 stop12h 12mMultiple Airlines
Deal found 10/29$203
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.
sáb. 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
dom. 1/114:55 pmYWG - ORD
1 stop26h 48mMultiple Airlines
Deal found 10/30$218
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.
jue. 12/45:05 amORD - YWG
2 stops19h 36mMultiple Airlines
dom. 12/77:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/30$228
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.
mar. 12/910:00 amORD - YWG
2 stops14h 41mMultiple Airlines
vie. 12/127:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/29$229
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.
mié. 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
mié. 1/77:30 amYWG - ORD
1 stop16h 31mMultiple Airlines
Deal found 10/29$289
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.
mié. 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
jue. 1/87:30 amYWG - ORD
1 stop13h 31mMultiple Airlines
Deal found 10/29$303
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.
dom. 11/95:01 amORD - YWG
1 stop10h 06mMultiple Airlines
lun. 11/1012:55 pmYWG - ORD
2 stops22h 19mMultiple Airlines
Deal found 10/29$316
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.
jue. 12/2512:39 pmORD - YWG
1 stop26h 28mMultiple Airlines
dom. 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$318
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.
mié. 12/3111:45 amORD - YWG
2 stops47h 35mMultiple Airlines
dom. 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$327
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.
mar. 12/306:00 amORD - YWG
2 stops38h 06mMultiple Airlines
jue. 1/87:30 amYWG - ORD
1 stop13h 31mMultiple Airlines
Deal found 10/29$332
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
vie. 11/216:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
dom. 11/237:30 amYWG - MDW
2 stops16h 43mMultiple Airlines
Deal found 10/28$341

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 octubre 30, 2025.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Chicago

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 12/4

7:23 pm-3:07 pm

1 stop19h 44m

Winnipeg

dom. 12/7

7:30 am-10:12 pm

1 stop14h 42m

$202

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 12/13

1:24 pm-3:07 pm

1 stop25h 43m

Winnipeg

dom. 1/11

4:55 pm-7:43 pm

1 stop26h 48m

$218

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

lun. 3/23

6:15 am-1:35 pm

1 stop7h 20m

$270

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 3/9

2:20 pm-11:52 am

1 stop21h 32m

Winnipeg

vie. 3/13

6:15 am-1:35 pm

1 stop7h 20m

$297

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 1/12

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

jue. 1/15

7:50 am-1:35 pm

1 stop29h 45m

$298

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 1/30

6:00 am-3:07 pm

1 stop9h 07m

Winnipeg

lun. 2/2

8:20 pm-10:05 am

1 stop13h 45m

$309

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 3/13

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

lun. 3/23

6:00 am-3:20 pm

1 stop9h 20m

$319

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

lun. 3/23

9:00 pm-5:12 pm

2 stops20h 12m

$376

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 12/4

4:21 pm-12:41 am

3 stops32h 20m

Winnipeg

dom. 12/7

12:55 pm-6:05 am

2 stops17h 10m

$396

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb. 12/13

9:59 am-12:42 am

2 stops14h 43m

Winnipeg

dom. 1/11

7:30 am-11:25 pm

1 stop15h 55m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 28 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
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 Chicago-Winnipeg flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. eDreams >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 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 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, May is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $91). Flying from Chicago to Winnipeg in November is currently the most expensive (average of $614). 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 octubre 30, 2025.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% 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 octubre 30, 2025.
Read reviews from past customers who have flown United Airlines and Air Canada 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
8,998 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,381 reviews
United Airlines
7.4
Good
8,998 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 1 inbound flight 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 8h 20m. WestJet provides one of the quickest options available for as low as $270. 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 Air Canada is currently your cheapest option to Winnipeg, with prices starting at $230. Another option worth looking into is United Airlines, starting at $415 round trip. These flights start at 57% lower than the current average price 3 months from now.

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

    One-way options have recently been found by users for as low as $273 on Air Canada. Other airlines that offer cheap prices include United Airlines from $285 and Porter Airlines from $362 one-way.

  • 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 (89%), Air Canada (89%) and United Airlines (89%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $1,004. On average you can expect to pay $1,090. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $209.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $91). Flying from Chicago to Winnipeg in November is currently the most expensive (average of $614). 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

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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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$614FlexibilityNo cancel feeOn-time69%

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