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Cheap flights from Illinois to Winnipeg from C$ 208

ORD — YWG
26 Sep — 3 Oct1
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

Fri 2/105:30 p.m. -
1 stop7h 25m
Sun 4/107:00 a.m. -
1 stop9h 40m
Deal found 22/8C$ 419
Thu 17/95:30 p.m. -
1 stop7h 25m
Sun 20/97:00 a.m. -
1 stop9h 40m
Deal found 22/8C$ 423
Tue 29/95:30 p.m. -
1 stop7h 25m
Tue 6/107:00 a.m. -
1 stop9h 40m
Deal found 25/8C$ 433
Wed 2/95:30 p.m. -
1 stop7h 25m
Sat 5/97:00 a.m. -
1 stop9h 40m
Deal found 23/8C$ 458
Fri 9/105:30 p.m. -
1 stop7h 25m
Fri 16/107:00 a.m. -
1 stop9h 40m
Deal found 25/8C$ 474
Thu 24/911:45 a.m. -
1 stop9h 00m
Mon 28/911:15 a.m. -
2 stops23h 45m
Deal found 23/8C$ 478
Mon 21/95:30 p.m. -
1 stop7h 25m
Mon 28/97:45 a.m. -
2 stops31h 35m
Deal found 22/8C$ 484
Fri 2/105:30 p.m. -
1 stop7h 25m
Sat 10/107:10 p.m. -
1 stop21h 30m
Deal found 26/8C$ 491
Mon 5/105:30 p.m. -
1 stop7h 25m
Mon 12/109:20 a.m. -
1 stop6h 59m
Deal found 25/8C$ 502
Fri 25/911:45 a.m. -
1 stop8h 04m
Sun 27/98:45 p.m. -
1 stop14h 15m
Deal found 26/8C$ 535
Mon 21/93:20 p.m. -
2 stops19h 23m
Mon 28/911:40 a.m. -
2 stops23h 20m
Deal found 24/8C$ 856
Fri 13/112:31 p.m. -
2 stops25h 54m
Sat 21/115:32 p.m. -
1 stop5h 46m
Deal found 26/8C$ 875

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 422

One-way from

C$ 208

Popular in

August

Cheapest in

February

Average price

C$ 1,742

Good one-way deal

C$ 467 or less
WestJet
  • WestJet
  • 2/10-4/10
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
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WestJet
  • WestJet
  • 18/9
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
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Highest demand for flights based on searches. 25% potential increase in price (C$ 504 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 96 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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Price to beat on a one-way flight from Illinois to Winnipeg.
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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

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 24/9

11:45 a.m.-8:45 p.m.

1 stop9h 00m

Winnipeg

Mon 28/9

11:15 a.m.-11:00 a.m.

2 stops23h 45m

C$ 478

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 9/10

8:40 p.m.-9:45 a.m.

1 stop13h 05m

Winnipeg

Fri 16/10

7:45 a.m.-7:48 p.m.

1 stop12h 03m

C$ 539

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sat 10/10

7:00 a.m.-4:40 p.m.

2 stops33h 40m

C$ 581

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 13/11

2:31 p.m.-4:25 p.m.

2 stops25h 54m

Winnipeg

Sat 21/11

5:32 p.m.-11:18 p.m.

1 stop5h 46m

C$ 875

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 9/10

6:47 a.m.-12:55 a.m.

2 stops18h 08m

Winnipeg

Fri 16/10

5:40 p.m.-10:38 a.m.

1 stop16h 58m

C$ 943

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 13/11

5:00 a.m.-12:23 p.m.

1 stop7h 23m

Winnipeg

Sat 21/11

8:40 a.m.-8:59 p.m.

1 stop12h 19m

C$ 948

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Sat 24/10

5:33 p.m.-11:48 a.m.

1 stop18h 15m

Winnipeg

Mon 2/11

8:35 p.m.-10:51 a.m.

2 stops14h 16m

C$ 953

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 10/10

3:15 p.m.-11:19 p.m.

2 stops8h 04m

Winnipeg

Sat 17/10

6:40 a.m.-4:39 p.m.

2 stops9h 59m

C$ 982

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 26/9

11:45 a.m.-5:58 p.m.

2 stops30h 13m

Winnipeg

Tue 29/9

11:40 a.m.-11:00 a.m.

2 stops23h 20m

C$ 990

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 2/10

1:55 p.m.-12:55 a.m.

2 stops11h 00m

Winnipeg

Sun 4/10

6:05 p.m.-12:59 p.m.

2 stops18h 54m

C$ 1,021

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/8

Showing 1-10 of 41 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$ 575). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,707). 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 (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like WestJet, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 12h 02m. The time it takes to get you to your destination can typically vary by up to 18h 11m. There are 1162 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 Copa Airlines (73%), SkyWest Airlines (63%) and Air Canada (63%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 543 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 467 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 496.

  • 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$ 575). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,707). 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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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.

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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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