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$104+ Cheap flights from Illinois 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.
ORD — YWG
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap flight deals from Illinois to Winnipeg

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 2025.

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.
Sat 12/277:05 pmORD - YWG
1 stop16h 40mWestJet
Tue 12/308:05 pmYWG - ORD
2 stops23h 33mWestJet
Deal found 12/16$841
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.
Sat 12/277:05 pmORD - YWG
1 stop4h 39mMultiple Airlines
Tue 12/306:00 amYWG - ORD
1 stop6h 33mMultiple Airlines
Deal found 12/16$872
This FlightHub deal was found by Cheapflights users on 12/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:01 pmORD - YWG
1 stop7h 43mWestJet
Sun 12/285:45 pmYWG - ORD
1 stop18h 05mWestJet
Deal found 12/17$904
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 12/254:01 pmORD - YWG
1 stop7h 43mMultiple Airlines
Sun 12/286:00 amYWG - ORD
1 stop8h 11mMultiple Airlines
Deal found 12/16$940
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 12/16. 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.
Sat 12/203:43 pmSTL - YWG
2 stops32h 52mWestJet
Mon 12/226:45 amYWG - STL
2 stops11h 35mWestJet
Deal found 12/16$1,059
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
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/229:29 amMDW - YWG
2 stops15h 13mWestJet
Thu 12/256:45 amYWG - MDW
2 stops10h 34mWestJet
Deal found 12/16$1,108
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.
Fri 12/191:50 pmMDW - YWG
1 stop21h 55mWestJet
Sun 12/215:45 pmYWG - MDW
1 stop17h 21mWestJet
Deal found 12/16$1,114
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:04 amSTL - YWG
3 stops16h 31mAmerican Airlines
Mon 12/226:00 amYWG - STL
2 stops17h 44mAmerican Airlines
Deal found 12/16$1,941

Find flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(oojo)

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 Illinois to Winnipeg
Search Deals
One-way flight from Illinois 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 Illinois to Winnipeg.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 17, 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

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

MDW - YWG

MDWYWG

Chicago Midway

Sat 1/31

9:38 am-3:09 pm

1 stop29h 31m

Winnipeg

Sat 2/7

9:00 pm-11:45 am

2 stops14h 45m

$253

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/16

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Thu 1/22

9:00 pm-1:35 pm

1 stop16h 35m

$261

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

Mon 1/19

2:20 pm-10:08 am

1 stop19h 48m

Winnipeg

Fri 1/23

6:15 am-1:35 pm

1 stop7h 20m

$263

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

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 1/31

8:22 pm-3:09 pm

1 stop18h 47m

Winnipeg

Sat 2/7

12:20 pm-11:33 pm

2 stops11h 13m

$270

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 2/26

5:05 am-12:40 am

2 stops19h 35m

Winnipeg

Sun 3/1

6:55 pm-1:35 pm

1 stop18h 40m

$278

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

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 39 results
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Best time to book a flight from Illinois to Winnipeg

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

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

Currently, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $89). Flying from Illinois 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 IL to YWG?

Find hourly flight availability from Illinois 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 17, 2025.

One of the essential ways to save on airfare from Illinois 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 39% on airfare.

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Illinois. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Illinois to Winnipeg?

    For as low as $432, WestJet can have you in Winnipeg from Illinois in 4h 53m. The distance from Illinois to Winnipeg is about 841 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Illinois to Winnipeg?

    While some choose either Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg, Chicago O'Hare Intl - Winnipeg is the most popular route from Illinois to Winnipeg.

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

    Consider SkyWest Airlines (59%), United Airlines (59%) or Air Canada (51%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Winnipeg.

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay $895 for a flight from Illinois to Winnipeg. The cheapest flight overall is $316 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $251.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $89). Flying from Illinois 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 Illinois to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Winnipeg

Discover the top 3 airlines that operate flights from Illinois 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 17, 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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