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Cheap flights from Illinois to Winnipeg from C$ 214

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 28/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 15 January 2026.

Round-trip from

C$ 315

One-way from

C$ 214

Popular in

January

Cheapest in

May

Average price

C$ 1,711
3/3-4/3
  • 3/3-4/3
  • 3 total stops
  • 24h 48m total
  • Illinois to Winnipeg
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28/2
  • 28/2
  • 2 total stops
  • 29h 57m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 518 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease (C$ 106 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 15 January 2026.

Tue 3/39:15 a.m.
ORD
-
YWG
2 stops15h 26m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 13/1C$ 315
Mon 13/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
WestJet
Fri 17/46:15 a.m.
YWG
-
ORD
1 stop7h 20m
WestJet
Deal found 13/1C$ 352
Fri 15/55:30 p.m.
ORD
-
YWG
1 stop29h 30m
WestJet
Sun 17/58:30 a.m.
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 14/1C$ 360
Fri 5/65:30 p.m.
ORD
-
YWG
1 stop21h 00m
WestJet
Sun 7/68:30 a.m.
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 14/1C$ 384
Thu 5/22:42 p.m.
ORD
-
YWG
1 stop24h 27m
Multiple Airlines
Sun 8/27:30 a.m.
YWG
-
ORD
1 stop14h 44m
Multiple Airlines
Deal found 14/1C$ 389
Tue 10/26:07 p.m.
ORD
-
YWG
1 stop21h 02m
Multiple Airlines
Thu 19/27:05 a.m.
YWG
-
ORD
2 stops30h 30m
Multiple Airlines
Deal found 13/1C$ 399
Tue 3/37:30 a.m.
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
Wed 4/38:20 p.m.
YWG
-
MDW
1 stop13h 45m
Multiple Airlines
Deal found 13/1C$ 403
Wed 4/27:20 a.m.
ORD
-
YWG
2 stops28h 12m
Multiple Airlines
Fri 6/26:15 a.m.
YWG
-
ORD
1 stop7h 20m
Multiple Airlines
Deal found 13/1C$ 404
Mon 13/44:21 p.m.
ORD
-
YWG
2 stops26h 48m
Multiple Airlines
Fri 17/46:15 a.m.
YWG
-
ORD
1 stop7h 20m
Multiple Airlines
Deal found 13/1C$ 428
Sun 1/36:00 a.m.
MDW
-
YWG
2 stops42h 41m
Multiple Airlines
Sun 8/37:30 a.m.
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Deal found 15/1C$ 478
Wed 18/27:00 a.m.
MDW
-
YWG
1 stop8h 09m
Multiple Airlines
Sat 21/26:15 a.m.
YWG
-
MDW
2 stops15h 18m
Multiple Airlines
Deal found 13/1C$ 517
Wed 11/26:30 a.m.
STL
-
YWG
1 stop5h 27m
United Airlines
Wed 18/22:20 p.m.
YWG
-
STL
1 stop7h 20m
United Airlines
Deal found 13/1C$ 548

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 15 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

Wed 4/2

7:20 a.m.-11:32 a.m.

2 stops28h 12m

Winnipeg

Fri 6/2

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

1 stop7h 20m

C$ 404

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 13/2

2:20 p.m.-12:40 a.m.

1 stop10h 20m

Winnipeg

Fri 20/2

12:10 p.m.-7:17 p.m.

1 stop7h 07m

C$ 442

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 19/2

5:15 a.m.-10:15 a.m.

2 stops29h 00m

Winnipeg

Mon 23/2

7:20 p.m.-7:11 p.m.

2 stops23h 51m

C$ 488

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 1/3

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

2 stops42h 41m

Winnipeg

Sun 8/3

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

1 stop12h 17m

C$ 495

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 10/2

6:07 p.m.-3:09 p.m.

1 stop21h 02m

Winnipeg

Tue 17/2

6:00 a.m.-4:41 p.m.

2 stops10h 41m

C$ 528

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 22/2

5:05 a.m.-3:09 p.m.

1 stop10h 04m

Winnipeg

Thu 26/2

9:00 p.m.-1:35 p.m.

1 stop16h 35m

C$ 532

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Sun 1/2

7:30 a.m.-10:46 p.m.

1 stop15h 16m

C$ 536

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 11/2

6:30 a.m.-11:57 a.m.

1 stop5h 27m

Winnipeg

Wed 18/2

2:20 p.m.-9:40 p.m.

1 stop7h 20m

C$ 548

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 2/3

4:05 p.m.-11:54 p.m.

1 stop7h 49m

Winnipeg

Wed 4/3

7:05 a.m.-3:29 p.m.

1 stop8h 24m

C$ 549

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 14/5

7:30 a.m.-2:23 p.m.

1 stop6h 53m

Winnipeg

Wed 20/5

5:10 a.m.-12:06 p.m.

1 stop6h 56m

C$ 549

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/1

Showing 1-10 of 43 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 15 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 15 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).

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 United Airlines, Air Canada, and Delta fly from Illinois to Winnipeg in about 5h 27m. The time it takes to get you to your destination can typically vary by up to 16h 49m. 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 (51%), Air Canada (51%) and United Airlines (51%).

  • 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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