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$166+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
2月 28 — 3月 71
土 2/28
土 3/7
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 1月 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
金 5/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
日 5/177:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/29$235
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
金 2/272:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
金 3/66:15 am
YWG
-
ORD
1 stop7h 20m
WestJet
Deal found 1/28$241
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
火 3/39:15 am
ORD
-
YWG
2 stops15h 26m
Multiple Airlines
水 3/47:30 am
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 1/29$258
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
金 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
土 6/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$267
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
金 2/272:20 pm
ORD
-
YWG
2 stops21h 47m
Multiple Airlines
金 3/67:30 am
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Deal found 1/28$275
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
金 3/132:20 pm
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
金 3/206:00 am
YWG
-
ORD
1 stop8h 10m
Multiple Airlines
Deal found 1/29$279
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
日 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
土 6/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$282
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
金 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
金 6/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$287
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
火 3/176:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
金 3/207:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Deal found 1/28$296
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
金 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
火 6/97:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$296
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
火 3/37:30 am
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
水 3/47:30 am
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 1/29$302
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
月 4/2011:00 am
MDW
-
YWG
1 stop13h 39m
Multiple Airlines
木 4/235:10 pm
YWG
-
MDW
1 stop16h 55m
Multiple Airlines
Deal found 1/29$319

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 1月 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Kiwi.com)

One-way from

$166
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$1,231

Good round-trip deal

$976 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. 30% potential increase in price ($274 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 January 2026
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 1月 29, 2026.
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

火 3/3

9:15 am-12:41 am

2 stops15h 26m

Winnipeg

水 3/4

7:30 am-4:52 pm

1 stop9h 22m

$263

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

火 3/17

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

金 3/20

7:30 am-7:47 pm

1 stop12h 17m

$296

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

火 3/3

7:30 am-12:40 am

2 stops17h 10m

Winnipeg

水 3/4

7:30 am-7:07 pm

1 stop11h 37m

$303

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

土 2/28

12:50 pm-12:39 am

1 stop11h 49m

Winnipeg

土 3/7

8:20 pm-2:20 pm

1 stop18h 00m

$327

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

金 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

金 3/20

7:30 am-8:25 am

2 stops24h 55m

$355

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

日 3/15

6:05 am-1:52 pm

2 stops55h 47m

Winnipeg

日 3/22

7:30 am-10:19 pm

1 stop14h 49m

$362

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

木 2/26

11:05 am-11:32 am

1 stop24h 27m

Winnipeg

日 3/1

8:20 pm-10:05 am

1 stop13h 45m

$367

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

金 2/27

6:00 am-3:09 pm

1 stop9h 09m

Winnipeg

金 3/6

7:30 am-7:47 pm

1 stop12h 17m

$370

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

金 2/27

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

金 3/6

7:30 am-9:13 pm

2 stops13h 43m

$374

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

木 2/26

8:16 pm-7:35 pm

2 stops23h 19m

Winnipeg

木 3/5

5:55 am-1:35 pm

2 stops31h 40m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 29 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 January.
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 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 1月 29, 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 evening could potentially save you up to 22% on airfare.

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago to Winnipeg. 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 1月 29, 2026.

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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 1月 29, 2026.
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
9,215 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
10,667 reviews
United Airlines
7.4
Good
9,215 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 3 inbound flights from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • 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 $263, respectively. 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 (54%), Air Canada (54%) and United Airlines (54%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $973. On average you can expect to pay $1,160. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $250.

  • 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.

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 1月 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$330FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$515FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$641FlexibilityNo cancel feeOn-time69%

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