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Cheap flights from Illinois to Winnipeg from C$ 127

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 20/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
7 Feb — 14 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 8 January 2026.

Round-trip from

C$ 315

One-way from

C$ 127

Popular in

February

Cheapest in

May
13/3-15/3
  • 13/3-15/3
  • 3 total stops
  • 32h 09m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 20/2
  • 1 total stop
  • 8h 20m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 291 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 34 potential savings vs. average RT price).
Search Deals

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 8 January 2026.

Wed 30/91:40 p.m.ORD - YWG
1 stop9h 30mWestJet
Sun 4/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 6/1C$ 307
Fri 13/32:20 p.m.ORD - YWG
1 stop8h 20mMultiple Airlines
Sun 15/34:10 p.m.YWG - ORD
2 stops23h 49mMultiple Airlines
Deal found 8/1C$ 315
Fri 20/22:20 p.m.ORD - YWG
1 stop8h 20mWestJet
Fri 27/26:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Deal found 6/1C$ 317
Sat 11/71:40 p.m.ORD - YWG
1 stop7h 45mWestJet
Fri 17/78:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 7/1C$ 318
Mon 11/55:30 p.m.ORD - YWG
1 stop18h 10mWestJet
Mon 1/68:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 6/1C$ 332
Fri 6/25:40 a.m.ORD - YWG
1 stop9h 29mMultiple Airlines
Sun 8/27:30 a.m.YWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 7/1C$ 340
Mon 2/28:43 p.m.ORD - YWG
2 stops18h 47mMultiple Airlines
Mon 9/28:00 a.m.YWG - ORD
1 stop27h 22mMultiple Airlines
Deal found 6/1C$ 348
Mon 2/22:20 p.m.ORD - YWG
1 stop10h 20mWestJet
Mon 9/26:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Deal found 6/1C$ 350
Sun 28/65:30 p.m.ORD - YWG
1 stop24h 10mWestJet
Thu 9/78:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 7/1C$ 351
Fri 5/65:30 p.m.ORD - YWG
1 stop18h 10mWestJet
Sun 7/68:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 8/1C$ 354
Wed 21/11:20 p.m.MDW - YWG
2 stops35h 21mMultiple Airlines
Sun 25/18:20 p.m.YWG - MDW
1 stop13h 50mMultiple Airlines
Deal found 7/1C$ 404
Tue 3/37:30 a.m.MDW - YWG
2 stops17h 10mMultiple Airlines
Wed 4/38:20 p.m.YWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 7/1C$ 415

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 8 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 13/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

Winnipeg

Sun 15/3

4:10 p.m.-3:59 p.m.

2 stops23h 49m

C$ 315

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 20/2

2:20 p.m.-10:40 p.m.

1 stop8h 20m

Winnipeg

Fri 27/2

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

1 stop7h 20m

C$ 317

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

Sun 7/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 354

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 20/2

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

1 stop10h 20m

Winnipeg

Fri 27/2

4:10 p.m.-4:53 p.m.

2 stops24h 43m

C$ 357

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-1:00 p.m.

2 stops19h 30m

Winnipeg

Mon 1/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 372

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/3

9:15 a.m.-12:41 a.m.

2 stops15h 26m

Winnipeg

Wed 4/3

7:30 a.m.-4:52 p.m.

1 stop9h 22m

C$ 397

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 21/1

1:20 p.m.-12:41 a.m.

2 stops35h 21m

Winnipeg

Sun 25/1

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

1 stop13h 50m

C$ 404

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

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

2 stops17h 10m

Winnipeg

Wed 4/3

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

1 stop13h 45m

C$ 415

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 13/3

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

1 stop9h 09m

Winnipeg

Sun 15/3

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

1 stop14h 49m

C$ 423

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 15/2

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

1 stop9h 09m

Winnipeg

Sun 22/2

7:30 a.m.-7:59 p.m.

1 stop12h 29m

C$ 463

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/1

Showing 1-10 of 38 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 8 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 8 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 WestJet, Delta, and Air Canada fly from Illinois to Winnipeg in about 5h 31m. The time it takes to get you to your destination can typically vary by up to 2h 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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