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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
5 Feb — 12 Feb1
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 6 January 2026.

Sat 22/81:40 p.m.ORD - YWG
1 stop7h 45mWestJet
Thu 27/88:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 4/1C$ 317
Sun 18/18:41 p.m.ORD - YWG
1 stop28h 02mMultiple Airlines
Fri 23/16:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Deal found 5/1C$ 330
Fri 5/65:30 p.m.ORD - YWG
1 stop21h 00mWestJet
Sun 7/68:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 5/1C$ 354
Fri 13/32:20 p.m.ORD - YWG
1 stop8h 20mWestJet
Sun 15/35:00 p.m.YWG - ORD
2 stops20h 35mWestJet
Deal found 4/1C$ 362
Mon 11/55:30 p.m.ORD - YWG
2 stops19h 30mWestJet
Mon 1/68:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Deal found 6/1C$ 370
Sat 18/71:40 p.m.ORD - YWG
1 stop9h 30mWestJet
Thu 23/75:30 p.m.YWG - ORD
1 stop23h 13mWestJet
Deal found 6/1C$ 374
Mon 2/29:00 a.m.ORD - YWG
1 stop15h 36mMultiple Airlines
Mon 9/28:00 a.m.YWG - ORD
1 stop27h 22mMultiple Airlines
Deal found 3/1C$ 379
Sun 25/15:01 p.m.MDW - YWG
2 stops31h 40mMultiple Airlines
Fri 30/17:30 a.m.YWG - MDW
1 stop14h 49mMultiple Airlines
Deal found 5/1C$ 385
Sun 25/15:40 a.m.ORD - YWG
1 stop9h 27mMultiple Airlines
Fri 30/17:30 a.m.YWG - ORD
1 stop15h 16mMultiple Airlines
Deal found 5/1C$ 390
Tue 3/39:50 a.m.MDW - YWG
2 stops9h 19mWestJet
Wed 4/35:19 p.m.YWG - MDW
1 stop19h 46mWestJet
Deal found 4/1C$ 460
Wed 4/21:20 p.m.MDW - YWG
2 stops35h 20mMultiple Airlines
Wed 11/24:55 p.m.YWG - MDW
1 stop30h 46mMultiple Airlines
Deal found 5/1C$ 501
Mon 19/15:25 p.m.STL - YWG
1 stop6h 13mDelta
Thu 22/15:21 p.m.YWG - STL
1 stop6h 04mDelta
Deal found 6/1C$ 542

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 6 January 2026.

Round-trip from

C$ 330

One-way from

C$ 186

Popular in

February

Cheapest in

May
WestJet
  • WestJet
  • 18/1-23/1
  • 2 total stops
  • 35h 22m total
  • Illinois to Winnipeg
Search Deals
24/2
  • 24/2
  • 1 total stop
  • 27h 18m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 288 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

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 6 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

Sun 18/1

8:41 p.m.-12:43 a.m.

1 stop28h 02m

Winnipeg

Fri 23/1

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

1 stop7h 20m

C$ 330

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

5:00 p.m.-1:35 p.m.

2 stops20h 35m

C$ 362

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

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

1 stop24h 10m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 365

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$ 370

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 25/1

5:01 p.m.-12:41 a.m.

2 stops31h 40m

Winnipeg

Fri 30/1

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

1 stop14h 49m

C$ 385

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 2/2

9:00 a.m.-12:36 a.m.

1 stop15h 36m

Winnipeg

Mon 9/2

9:00 p.m.-10:51 a.m.

2 stops13h 51m

C$ 399

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 25/1

6:41 a.m.-12:43 a.m.

1 stop18h 02m

Winnipeg

Fri 30/1

7:30 a.m.-9:03 p.m.

2 stops13h 33m

C$ 401

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 14/2

7:55 a.m.-1:52 p.m.

2 stops29h 57m

Winnipeg

Sun 22/2

7:30 a.m.-10:39 p.m.

1 stop15h 09m

C$ 420

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 25/2

8:10 a.m.-12:41 a.m.

2 stops16h 31m

Winnipeg

Thu 26/2

7:30 a.m.-5:24 p.m.

1 stop9h 54m

C$ 425

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

9:50 a.m.-7:09 p.m.

2 stops9h 19m

Winnipeg

Wed 4/3

5:19 p.m.-1:05 p.m.

1 stop19h 46m

C$ 460

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/1

Showing 1-10 of 35 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 6 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 6 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 United Airlines fly from Illinois to Winnipeg in about 5h 32m. The time it takes to get you to your destination can typically vary by up to 15h 28m. 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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