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Cheap flights from Illinois to Winnipeg from C$ 252

ORD — YWG
28 Oct — 4 Nov1
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

Thu 22/105:30 p.m. -
1 stop7h 25m
Fri 30/109:35 p.m. -
2 stops15h 16m
Deal found 27/9C$ 575
Thu 22/105:30 p.m. -
1 stop7h 25m
Thu 29/106:00 a.m. -
2 stops12h 45m
Deal found 27/9C$ 578
Tue 22/128:10 a.m. -
1 stop30h 30m
Tue 5/18:35 p.m. -
2 stops15h 15m
Deal found 27/9C$ 592
Thu 22/105:30 p.m. -
1 stop7h 25m
Mon 2/118:35 p.m. -
2 stops16h 16m
Deal found 28/9C$ 605
Thu 22/105:30 p.m. -
1 stop7h 25m
Tue 3/118:35 p.m. -
2 stops16h 16m
Deal found 28/9C$ 606
Thu 29/107:50 p.m. -
2 stops21h 35m
Sun 1/118:35 p.m. -
2 stops22h 10m
Deal found 25/9C$ 609
Thu 22/105:30 p.m. -
1 stop7h 25m
Thu 12/118:35 p.m. -
2 stops22h 10m
Deal found 28/9C$ 613
Thu 12/116:20 p.m. -
1 stop15h 55m
Mon 16/117:00 a.m. -
1 stop10h 40m
Deal found 25/9C$ 619

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 575

One-way from

C$ 252

Popular in

August

Cheapest in

February

Average price

C$ 725
22/10-30/10
  • 22/10-30/10
  • 3 total stops
  • 22h 41m total
  • Illinois to Winnipeg
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2/11-31/12
  • 2/11-31/12
  • 2 total stops
  • 28h 20m total
  • Illinois to Winnipeg
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Highest demand for flights based on searches. 16% potential increase in price (C$ 298 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 125 potential savings vs. average RT price).
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Average for round-trip flights in September 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.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 30/10

7:50 p.m.-1:10 a.m.

2 stops29h 20m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 268

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 7/11

7:15 a.m.-12:10 a.m.

2 stops16h 55m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 288

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 14/10

8:30 a.m.-12:55 a.m.

3 stops40h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 314

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 10/2

6:00 a.m.-4:25 p.m.

2 stops34h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 341

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 22/10

5:30 p.m.-8:20 p.m.

1 stop26h 50m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 411

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sun 11/10

6:20 a.m.-11:10 a.m.

3 stops52h 50m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 491

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 30/10

8:30 p.m.-9:57 p.m.

1 stop25h 27m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 500

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 9/10

6:39 p.m.-12:55 a.m.

3 stops30h 16m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 510

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 30/10

7:50 p.m.-5:25 p.m.

2 stops21h 35m

Winnipeg

Mon 2/11

8:35 p.m.-5:03 p.m.

3 stops20h 28m

C$ 697

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 30/10

8:30 p.m.-9:57 p.m.

1 stop25h 27m

Winnipeg

Mon 2/11

7:00 a.m.-2:37 p.m.

1 stop7h 37m

C$ 826

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/9

Showing 1-10 of 19 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, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 678). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,743). 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 (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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

Airfare is typical for this route at the moment.
Illinois to Winnipeg flights typically cost between C$ 351 and C$ 1,504 in October.
The cheapest round-trip price found within the last 5 days was C$ 575 on Multiple Airlines (22 Oct-30 Oct).

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.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like Porter Airlines fly from Illinois to Winnipeg in about 25h 27m. The time it takes to get you to your destination can typically vary by up to . There are 1136 km between Illinois and 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 SkyWest Airlines (67%), Air Canada (67%) and United Airlines (67%).

  • 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, October is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 678). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,743). 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

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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.

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Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

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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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