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$102+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$556

Good round-trip deal

$415 or less
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 ($5 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 September 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 septiembre 15, 2025.

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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$208
This Vliegwinkel 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/95:30 pmORD - YWG
1 stop29h 40mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$211
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.
vie. 10/105:30 pmORD - YWG
1 stop18h 11mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$215
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.
sáb. 10/115:30 pmORD - YWG
2 stops17h 56mWestJet
vie. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$216
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.
dom. 10/125:30 pmORD - YWG
1 stop15h 31mWestJet
vie. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$218
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.
jue. 10/165:30 pmORD - YWG
1 stop18h 11mWestJet
vie. 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/13$232
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.
lun. 10/65:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$233
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.
mié. 10/83:12 pmORD - YWG
1 stop25h 10mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$234
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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
jue. 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Deal found 9/14$235
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.
sáb. 10/115:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$236
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.
mar. 10/281:56 pmMDW - YWG
1 stop25h 11mMultiple Airlines
mar. 11/49:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
Deal found 9/12$256
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.
vie. 10/106:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
lun. 10/139:05 pmYWG - MDW
2 stops16h 33mMultiple Airlines
Deal found 9/12$327

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 septiembre 15, 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

jue. 10/9

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

dom. 10/12

8:30 am-4:43 pm

1 stop8h 13m

$208

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/16

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

vie. 10/24

8:30 am-4:43 pm

1 stop8h 13m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 10/10

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

mié. 10/15

9:05 pm-4:43 pm

1 stop19h 38m

$241

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 10/10

5:30 pm-5:40 pm

1 stop24h 10m

Winnipeg

lun. 10/13

9:00 am-11:44 pm

1 stop14h 44m

$244

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 10/28

1:56 pm-3:07 pm

1 stop25h 11m

Winnipeg

mar. 11/4

9:00 pm-12:41 pm

2 stops15h 41m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 10/6

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

jue. 10/16

9:00 am-11:39 pm

1 stop14h 39m

$273

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/9

1:26 pm-12:30 am

2 stops11h 04m

Winnipeg

dom. 10/12

8:30 am-4:43 pm

1 stop8h 13m

$275

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 11/17

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

dom. 11/23

12:55 pm-1:35 pm

3 stops24h 40m

$316

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 10/4

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

dom. 10/5

6:30 am-8:20 pm

2 stops13h 50m

$325

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 10/10

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

lun. 10/13

9:05 pm-1:38 pm

2 stops16h 33m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 35 results
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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, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in December is currently the most expensive (average of $501). 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 septiembre 15, 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 14% 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 septiembre 15, 2025.

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

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 septiembre 15, 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
8,929 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 7 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 15h 31m. WestJet provides one of the quickest options available for as low as $208. There are 706 mi between Chicago and Winnipeg.

  • 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 most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (76%), Air Canada (76%) and United Airlines (76%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $183. On average you can expect to pay $663. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $239.

  • 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, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in December is currently the most expensive (average of $501). 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$542FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$615FlexibilityNo cancel feeOn-time69%

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