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Cheap flights from Illinois to Winnipeg from C$ 160

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
28 Feb — 7 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 29 January 2026.

Fri 27/22:20 p.m.
ORD
-
YWG
1 stop8h 20m
WestJet
Fri 6/36:15 a.m.
YWG
-
ORD
1 stop7h 20m
WestJet
Deal found 28/1C$ 327
Fri 1/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 6/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 362
Fri 27/22:20 p.m.
ORD
-
YWG
2 stops21h 47m
Multiple Airlines
Fri 6/37:30 a.m.
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Deal found 28/1C$ 373
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 6/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 383
Fri 1/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 390
Tue 17/36:00 a.m.
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Fri 20/37:30 a.m.
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Deal found 28/1C$ 402
Fri 1/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 9/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 402
Fri 6/35:05 a.m.
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Mon 9/38:00 a.m.
YWG
-
ORD
1 stop15h 47m
Multiple Airlines
Deal found 27/1C$ 405
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 410
Tue 17/39:28 a.m.
ORD
-
YWG
2 stops15h 12m
Multiple Airlines
Fri 20/37:30 a.m.
YWG
-
ORD
1 stop15h 09m
Multiple Airlines
Deal found 28/1C$ 411
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 9/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 28/1C$ 422
Wed 25/26:02 p.m.
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 28/1C$ 425

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 29 January 2026.

Round-trip from

C$ 327

One-way from

C$ 160

Popular in

January

Cheapest in

May

Average price

C$ 1,671
WestJet
  • WestJet
  • 27/2-6/3
  • 2 total stops
  • 15h 40m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 3/6
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 30% potential increase in price (C$ 505 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease (C$ 102 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 29 January 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 1/5

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

1 stop7h 25m

Winnipeg

Sat 6/6

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

1 stop9h 40m

C$ 362

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 27/2

2:20 p.m.-12:07 p.m.

2 stops21h 47m

Winnipeg

Fri 6/3

7:30 a.m.-11:16 a.m.

1 stop27h 46m

C$ 373

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 17/3

6:00 a.m.-12:40 a.m.

2 stops18h 40m

Winnipeg

Fri 20/3

7:30 a.m.-7:47 p.m.

1 stop12h 17m

C$ 402

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/5

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

1 stop7h 25m

Winnipeg

Mon 8/6

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 430

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

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

1 stop7h 25m

Winnipeg

Fri 15/5

9:05 p.m.-10:44 a.m.

2 stops13h 39m

C$ 482

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/5

5:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Thu 11/6

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

1 stop9h 40m

C$ 497

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 26/2

11:05 a.m.-11:32 a.m.

1 stop24h 27m

Winnipeg

Sun 1/3

8:20 p.m.-10:05 a.m.

1 stop13h 45m

C$ 498

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 27/2

6:00 a.m.-3:09 p.m.

1 stop9h 09m

Winnipeg

Fri 6/3

7:30 a.m.-7:47 p.m.

1 stop12h 17m

C$ 502

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop7h 25m

Winnipeg

Sun 7/6

11:45 a.m.-4:40 p.m.

2 stops28h 55m

C$ 516

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 25/2

8:16 p.m.-12:40 a.m.

3 stops28h 24m

Winnipeg

Wed 4/3

7:30 a.m.-11:47 p.m.

2 stops16h 17m

C$ 532

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

Showing 1-10 of 33 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 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 29 January 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 29 January 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).

How much does it cost to fly round-trip from Illinois to Winnipeg?

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 and Air Canada fly from Illinois to Winnipeg in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 54m. There are 1136 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

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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.

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