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Cheap flights from Illinois to Winnipeg from C$ 188

ORD — YWG
7 Oct — 14 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

Sun 11/105:30 p.m. -
1 stop7h 25m
Sun 18/107:00 a.m. -
1 stop9h 40m
Deal found 3/9C$ 437
Thu 15/105:30 p.m. -
1 stop7h 25m
Mon 19/107:00 a.m. -
1 stop9h 40m
Deal found 6/9C$ 457
Sun 4/105:30 p.m. -
1 stop7h 25m
Sun 11/107:00 a.m. -
1 stop9h 40m
Deal found 6/9C$ 461
Sun 4/105:30 p.m. -
1 stop7h 25m
Wed 7/109:20 a.m. -
1 stop6h 54m
Deal found 3/9C$ 517
Fri 18/95:30 p.m. -
1 stop7h 25m
Mon 21/92:55 p.m. -
1 stop25h 45m
Deal found 4/9C$ 519
Fri 2/105:30 p.m. -
1 stop7h 25m
Fri 9/106:15 a.m. -
2 stops33h 15m
Deal found 4/9C$ 524
Fri 2/105:30 p.m. -
1 stop7h 25m
Sat 10/107:10 p.m. -
1 stop21h 30m
Deal found 4/9C$ 527
Tue 29/95:30 p.m. -
1 stop7h 25m
Tue 6/109:20 a.m. -
1 stop6h 54m
Deal found 3/9C$ 530
Mon 5/105:30 p.m. -
1 stop7h 25m
Mon 12/105:00 p.m. -
2 stops37h 34m
Deal found 5/9C$ 534
Mon 19/108:04 a.m. -
2 stops16h 51m
Mon 26/104:00 p.m. -
1 stop13h 16m
Deal found 4/9C$ 537
Thu 1/1012:17 p.m. -
1 stop12h 18m
Thu 5/118:35 p.m. -
2 stops21h 05m
Deal found 7/9C$ 675
Fri 2/102:29 p.m. -
2 stops31h 41m
Thu 12/114:00 p.m. -
1 stop20h 33m
Deal found 7/9C$ 678

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 437

One-way from

C$ 188

Popular in

August

Cheapest in

February

Good one-way deal

C$ 541 or less
WestJet
  • WestJet
  • 11/10-18/10
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
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Porter Airlines
  • Porter Airlines
  • 20/10-31/12
  • 2 total stops
  • 26h 38m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 29% potential increase in price (C$ 628 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease (C$ 128 potential savings vs. average RT price).
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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

Tue 20/10

3:20 p.m.-5:58 p.m.

2 stops26h 38m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 188

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 17/10

3:20 p.m.-9:45 a.m.

1 stop18h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 201

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Wed 14/10

3:20 p.m.-10:43 a.m.

2 stops19h 23m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 201

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 15/10

3:20 p.m.-9:45 a.m.

1 stop18h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 213

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 14/10

2:15 p.m.-12:55 a.m.

1 stop10h 40m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 220

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 18/9

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

1 stop7h 25m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 223

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Wed 21/10

6:35 p.m.-12:55 a.m.

3 stops30h 20m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 228

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 16/10

5:30 p.m.-10:10 p.m.

1 stop28h 40m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 252

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 16/10

11:05 a.m.-12:55 a.m.

2 stops13h 50m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 275

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 16/10

3:20 p.m.-5:58 p.m.

2 stops26h 38m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 278

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 44 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$ 663). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,703). 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 (6 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$ 353 and C$ 1,590 in October.
The cheapest round-trip price found within the last 5 days was C$ 437 on WestJet (11 Oct-18 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 Air Canada, Porter Airlines, and WestJet fly from Illinois to Winnipeg in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 16h 25m. There are 1136 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 (65%), SkyWest Airlines (64%) and Air Canada (64%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 581 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 466 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 534.

  • 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$ 663). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,703). 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.

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

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