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$104+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 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.
Wed 12/243:51 pmORD - YWG
2 stops28h 12mMultiple Airlines
Tue 12/308:00 amYWG - ORD
1 stop30h 21mMultiple Airlines
Deal found 12/14$742
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.
Thu 12/259:33 pmORD - YWG
1 stop27h 50mMultiple Airlines
Wed 12/314:55 pmYWG - ORD
2 stops17h 23mMultiple Airlines
Deal found 12/14$761
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.
Thu 12/259:33 pmORD - YWG
1 stop27h 50mMultiple Airlines
Tue 12/308:00 amYWG - ORD
1 stop30h 21mMultiple Airlines
Deal found 12/14$771
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.
Thu 12/259:33 pmORD - YWG
1 stop27h 50mMultiple Airlines
Mon 12/294:55 pmYWG - ORD
2 stops21h 22mMultiple Airlines
Deal found 12/14$853
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 12/277:05 pmORD - YWG
1 stop4h 39mMultiple Airlines
Tue 12/306:00 amYWG - ORD
1 stop6h 33mMultiple Airlines
Deal found 12/14$871
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.
Wed 12/249:05 pmORD - YWG
2 stops26h 49mUnited Airlines
Tue 12/302:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Deal found 12/14$875
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.
Sat 12/276:02 pmORD - YWG
2 stops25h 25mWestJet
Tue 12/308:05 pmYWG - ORD
2 stops23h 33mWestJet
Deal found 12/15$884
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.
Thu 12/256:35 amORD - YWG
2 stops18h 04mWestJet
Mon 12/295:55 amYWG - ORD
2 stops36h 05mWestJet
Deal found 12/14$908
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:32 pmORD - YWG
1 stop11h 11mMultiple Airlines
Thu 12/255:55 amYWG - ORD
2 stops14h 28mMultiple Airlines
Deal found 12/16$911
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - YWG
2 stops19h 11mMultiple Airlines
Sun 12/216:40 amYWG - MDW
1 stop4h 26mMultiple Airlines
Deal found 12/16$919
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:59 pmMDW - YWG
1 stop5h 45mWestJet
Sun 12/288:05 pmYWG - MDW
2 stops21h 21mWestJet
Deal found 12/16$1,030
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.
Tue 12/235:59 pmMDW - YWG
1 stop5h 45mWestJet
Fri 12/268:05 pmYWG - MDW
2 stops21h 21mWestJet
Deal found 12/15$1,071

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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(Kiwi.com)

One-way from

$104
(Trip.com)

Popular in

February

Cheapest in

May

Average price

$689

Good round-trip deal

$316 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. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 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 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 December 16, 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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 2/3

2:53 pm-3:09 pm

1 stop24h 16m

Winnipeg

Sat 2/7

9:00 pm-1:37 pm

2 stops16h 37m

$251

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Sun 6/7

8:30 am-4:43 pm

1 stop8h 13m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 1/28

8:10 am-12:41 am

2 stops16h 31m

Winnipeg

Fri 2/6

6:15 am-1:35 pm

1 stop7h 20m

$261

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/25

12:40 pm-1:35 pm

1 stop24h 55m

$264

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 1/29

2:42 pm-3:07 pm

1 stop24h 25m

Winnipeg

Thu 2/5

12:10 pm-11:22 am

2 stops23h 12m

$281

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 1/11

8:43 pm-11:35 am

2 stops38h 52m

Winnipeg

Mon 1/19

8:00 am-11:22 am

1 stop27h 22m

$287

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 1/23

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Sun 1/25

2:40 pm-11:45 am

2 stops21h 05m

$294

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/22

11:05 am-12:42 am

1 stop13h 37m

Winnipeg

Sat 1/24

9:00 pm-11:45 am

2 stops14h 45m

$330

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/29

5:01 pm-3:07 pm

1 stop22h 06m

Winnipeg

Thu 2/5

8:20 pm-8:52 am

2 stops12h 32m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 29 results
1
2
3

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 December.
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 $89). 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 December 16, 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 December 16, 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
9,092 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,531 reviews
United Airlines
7.4
Good
9,092 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 3 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 18h 10m. WestJet provides one of the quickest options available for as low as $257. There are 706 mi between Chicago and Winnipeg.

  • 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. Additional round-trip tickets that might be worth considering are offered by Air Canada and United Airlines, with the lowest prices starting at $230 and $266, respectively. These flights start at 71% 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 (73%), United Airlines (73%) and Air Canada (70%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $316. On average you can expect to pay $895. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $251.

  • 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 $89). 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

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 3 airlines flying from Chicago to Winnipeg

Discover the top 3 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$675FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$585FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$648FlexibilityNo cancel feeOn-time69%

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