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Cheap flights from Illinois to Winnipeg from C$ 297

ORD — YWG
25 Nov — 2 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

Thu 3/126:20 p.m. -
1 stop14h 55m
Sun 6/127:55 p.m. -
1 stop16h 40m
Deal found 24/10C$ 527
Thu 10/126:20 p.m. -
1 stop14h 55m
Sun 13/129:35 p.m. -
2 stops25h 07m
Deal found 22/10C$ 531
Tue 1/123:55 p.m. -
2 stops32h 15m
Wed 9/124:00 p.m. -
1 stop19h 32m
Deal found 23/10C$ 646
Mon 21/125:58 a.m. -
1 stop7h 42m
Thu 28/19:35 p.m. -
2 stops15h 15m
Deal found 26/10C$ 650
Sat 21/116:20 p.m. -
1 stop14h 55m
Mon 23/117:55 p.m. -
1 stop14h 28m
Deal found 22/10C$ 681
Tue 1/123:55 p.m. -
2 stops32h 15m
Tue 8/128:00 a.m. -
1 stop18h 08m
Deal found 25/10C$ 703

Find flight deals from Illinois to Winnipeg

Round-trip from

C$ 527

One-way from

C$ 289

Popular in

August

Cheapest in

February

Average price

C$ 1,144
3/12-6/12
  • 3/12-6/12
  • 2 total stops
  • 31h 35m total
  • Illinois to Winnipeg
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21/1-31/12
  • 21/1-31/12
  • 2 total stops
  • 23h 50m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 250 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 119 potential savings vs. average RT price).
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Average for round-trip flights in October 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

Mon 7/12

4:08 p.m.-5:25 p.m.

3 stops24h 17m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 353

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 7/12

2:50 p.m.-10:57 p.m.

1 stop7h 07m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 363

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 4/12

3:55 p.m.-1:10 a.m.

3 stops32h 15m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 364

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 11/11

7:35 p.m.-5:25 p.m.

2 stops20h 50m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 380

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/12

4:08 p.m.-5:25 p.m.

3 stops24h 17m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 412

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 23/11

2:50 p.m.-10:52 p.m.

1 stop7h 02m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 450

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Fri 4/12

2:50 p.m.-10:57 p.m.

1 stop7h 07m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 450

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/12

2:50 p.m.-10:57 p.m.

1 stop7h 07m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 450
Quickest round-trip

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 10/12

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$ 609

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Mon 7/12

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$ 609

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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$ 717). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,724). 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.

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 SkyWest Airlines (77%), United Airlines (77%) and Air Canada (77%).

  • 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$ 717). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,724). 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

Browse thousands of different options on Cheapflights for your next trip

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Fly with Cheapflights

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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