Find flights
Deals
When to book
FAQs

Cheap flights from Illinois to Winnipeg from C$ 226

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
4 Mar — 11 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Winnipeg

Enter your travel dates to find the best prices.

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 2 February 2026.

Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 18/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 31/1C$ 290
Thu 5/34:42 p.m.
ORD
-
YWG
1 stop22h 27m
Multiple Airlines
Mon 9/39:00 p.m.
YWG
-
ORD
2 stops21h 41m
Multiple Airlines
Deal found 31/1C$ 319
Fri 8/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 10/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/2C$ 336
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 17/510:15 p.m.
YWG
-
ORD
2 stops18h 25m
WestJet
Deal found 31/1C$ 387
Fri 8/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 10/59:05 p.m.
YWG
-
ORD
2 stops13h 39m
Multiple Airlines
Deal found 1/2C$ 400
Mon 11/55:30 p.m.
ORD
-
YWG
1 stop26h 45m
WestJet
Mon 1/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 31/1C$ 418
Thu 26/25:16 p.m.
MDW
-
YWG
1 stop21h 53m
Multiple Airlines
Mon 2/39:00 p.m.
YWG
-
MDW
2 stops22h 07m
Multiple Airlines
Deal found 31/1C$ 463
Tue 3/37:30 a.m.
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 1/2C$ 490
Wed 25/27:00 a.m.
MDW
-
YWG
1 stop8h 09m
Multiple Airlines
Mon 2/39:00 p.m.
YWG
-
MDW
2 stops22h 07m
Multiple Airlines
Deal found 1/2C$ 516
Fri 20/36:05 a.m.
MDW
-
YWG
2 stops18h 35m
Multiple Airlines
Sun 22/37:30 a.m.
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Deal found 1/2C$ 547
Wed 18/311:32 a.m.
STL
-
YWG
2 stops13h 08m
Multiple Airlines
Wed 25/37:30 a.m.
YWG
-
STL
1 stop27h 01m
Multiple Airlines
Deal found 1/2C$ 575
Thu 14/57:30 a.m.
STL
-
YWG
1 stop6h 48m
Air Canada
Wed 20/511:00 a.m.
YWG
-
STL
1 stop9h 05m
Air Canada
Deal found 31/1C$ 577

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 2 February 2026.

Round-trip from

C$ 290

One-way from

C$ 226

Popular in

January

Cheapest in

May

Average price

C$ 1,024
WestJet
  • WestJet
  • 15/5-18/5
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
18/3
  • 18/3
  • 3 total stops
  • 53h 47m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 30% potential increase in price (C$ 508 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 103 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 629,999 searches. Data last updated 2 February 2026.
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

Fri 15/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 18/5

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 290

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/3

4:42 p.m.-3:09 p.m.

1 stop22h 27m

Winnipeg

Mon 9/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 344

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 26/2

5:16 p.m.-3:09 p.m.

1 stop21h 53m

Winnipeg

Mon 2/3

9:00 p.m.-7:07 p.m.

2 stops22h 07m

C$ 463

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

7:30 a.m.-12:40 a.m.

2 stops17h 10m

Winnipeg

Wed 4/3

7:30 a.m.-7:07 p.m.

1 stop11h 37m

C$ 490

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 26/2

6:00 a.m.-12:41 a.m.

2 stops18h 41m

Winnipeg

Mon 2/3

8:00 a.m.-11:22 a.m.

1 stop27h 22m

C$ 531

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-12:15 p.m.

1 stop18h 45m

Winnipeg

Mon 1/6

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 538

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 17/3

7:41 p.m.-12:40 a.m.

2 stops28h 59m

Winnipeg

Tue 24/3

5:20 p.m.-9:26 p.m.

1 stop4h 06m

C$ 545

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 20/3

6:05 a.m.-12:40 a.m.

2 stops18h 35m

Winnipeg

Sun 22/3

7:30 a.m.-10:19 p.m.

1 stop14h 49m

C$ 547

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 15/5

5:30 p.m.-3:55 p.m.

3 stops22h 25m

Winnipeg

Sun 17/5

5:25 p.m.-4:40 p.m.

2 stops23h 15m

C$ 572

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 18/3

11:32 a.m.-12:40 a.m.

2 stops13h 08m

Winnipeg

Wed 25/3

7:30 a.m.-10:31 a.m.

1 stop27h 01m

C$ 575

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/2

Showing 1-10 of 42 results
1
2
3
...
5

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 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 2 February 2026.

When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois 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 2 February 2026.

The most flights from USIL 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).

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?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly into when you book flights from Illinois to Winnipeg.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like WestJet, Air Canada, and Delta fly from Illinois to Winnipeg in about 4h 32m. The time it takes to get you to your destination can typically vary by up to 2h 53m. There are 1353 km between Illinois and Winnipeg. This flight may include one or multiple stops.

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

    The most popular route from Illinois to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg.

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

    The top 3 most reliable airlines when flying from Illinois to Winnipeg are SkyWest Airlines (54%), Air Canada (54%) and United Airlines (54%).

  • 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.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Dulles Intl to Winnipeg flights
Minneapolis to Winnipeg flights
Sky Harbor Intl to Winnipeg flights
Denver to Winnipeg flights
Reagan-National to Winnipeg flights
Milwaukee to Winnipeg flights
Los Angeles to Winnipeg flights
George Bush Intcntl to Winnipeg flights
Baltimore to Winnipeg flights
Seattle to Winnipeg flights
Newark to Winnipeg flights
Atlanta to Winnipeg flights
San Francisco to Winnipeg flights
LaGuardia to Winnipeg flights
Hobby to Winnipeg flights
Dallas/Fort Worth to Winnipeg flights
Orlando to Winnipeg flights
Ontario to Winnipeg flights
San Diego to Winnipeg flights
John F Kennedy Intl to Winnipeg flights
Austin to Winnipeg flights
Philadelphia to Winnipeg flights
St. Louis to Winnipeg flights
Fort Myers to Winnipeg flights
Boston to Winnipeg flights
Detroit to Winnipeg flights
Las Vegas to Winnipeg flights
Fort Lauderdale to Winnipeg flights
Portland to Winnipeg flights
Oakland to Winnipeg flights
Madison to Winnipeg flights
Santa Ana to Winnipeg flights
Tampa to Winnipeg flights
San Antonio to Winnipeg flights
Cincinnati to Winnipeg flights
Fargo to Winnipeg flights
Spokane to Winnipeg flights
Columbus to Winnipeg flights
Salt Lake City to Winnipeg flights
Richmond to Winnipeg flights
San Jose to Winnipeg flights
Bismarck to Winnipeg flights
Buffalo to Winnipeg flights
Charlotte to Winnipeg flights
New Orleans to Winnipeg flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Illinois to Winnipeg?

Cheapflights makes it easy to find Illinois to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Illinois to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Illinois.

Can Cheapflights find flights from Illinois to Winnipeg with no change fees?

Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from Illinois to Winnipeg become cheaper?

Yes! Start tracking prices for Illinois to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.