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Cheap flights from Illinois to Winnipeg from C$ 250

ORD — YWG
10 Dec — 17 Dec1
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

Wed 9/128:30 a.m. -
2 stops15h 40m
Sat 12/1211:00 a.m. -
1 stop25h 34m
Deal found 6/11C$ 598
Thu 3/1210:29 p.m. -
2 stops17h 56m
Sun 6/127:55 p.m. -
1 stop16h 39m
Deal found 9/11C$ 622
Thu 10/1210:29 p.m. -
2 stops17h 56m
Fri 11/129:35 p.m. -
2 stops17h 55m
Deal found 5/11C$ 624
Fri 11/1210:29 p.m. -
2 stops17h 56m
Sun 13/127:55 p.m. -
1 stop16h 39m
Deal found 6/11C$ 641
Thu 10/126:21 a.m. -
1 stop16h 24m
Sat 12/124:45 p.m. -
2 stops13h 16m
Deal found 5/11C$ 698

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 542

One-way from

C$ 250

Popular in

August

Cheapest in

February

Average price

C$ 635
27/1-29/1
  • 27/1-29/1
  • 3 total stops
  • 22h 55m total
  • Illinois to Winnipeg
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8/12-31/12
  • 8/12-31/12
  • 2 total stops
  • 15h 40m total
  • Illinois to Winnipeg
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Highest demand for flights based on searches. 13% potential increase in price (C$ 254 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 120 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/12

10:29 p.m.-5:25 p.m.

2 stops17h 56m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 275

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 30/11

12:15 p.m.-7:14 p.m.

2 stops29h 59m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 358

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 22/12

5:59 p.m.-5:25 p.m.

2 stops22h 26m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 375

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 30/11

9:20 p.m.-1:10 a.m.

3 stops26h 50m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 394

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 20/12

7:35 a.m.-12:59 a.m.

3 stops16h 24m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 552
Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 30/11

9:35 a.m.-1:23 p.m.

Nonstop2h 48m

Winnipeg

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 652

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/12

10:29 p.m.-5:25 p.m.

2 stops17h 56m

Winnipeg

Sat 12/12

9:35 p.m.-1:08 a.m.

3 stops28h 33m

C$ 700

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 9/3

8:25 a.m.-10:15 a.m.

2 stops24h 50m

Winnipeg

Mon 15/3

7:00 a.m.-11:23 p.m.

1 stop16h 23m

C$ 796

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 11/12

6:21 a.m.-10:55 p.m.

3 stops15h 34m

Winnipeg

Sun 13/12

3:10 p.m.-10:24 a.m.

2 stops20h 14m

C$ 855

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 7/1

8:00 a.m.-11:49 a.m.

1 stop26h 49m

Winnipeg

Sun 10/1

6:54 a.m.-1:10 p.m.

1 stop7h 16m

C$ 1,062

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 14 resultsSorted by cheapest first
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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

Cheapflights Insights

Everything you need to know about your flight from Illinois to Winnipeg

What is the cheapest month to book a flight from Illinois to Winnipeg?

Currently, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 722). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,737). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to YWG?

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

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

  • 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.

  • 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 Copa Airlines (84%), SkyWest Airlines (80%) and United Airlines (80%).

  • 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.

  • What is the cheapest month to book a flight from Illinois to Winnipeg?

    Currently, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 722). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,737). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Winnipeg?

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

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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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