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Cheap flights from Illinois to Winnipeg from $74

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Winnipeg departing on 2/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Illinois to Winnipeg

Cheap round-trip flights

WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$206WestJet
Find Deal
Thu, Oct 16 - Sat, Oct 18
WestJet Logo
5:30 pm - 2:30 pmORD-YWG
21h 00m1 stop
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
$213WestJet
Find Deal
Sun, Oct 19 - Sun, Oct 26
Logo
11:00 am - 12:30 amORD-YWG
13h 30m2 stops
Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$215
Find Deal
Wed, Oct 22 - Sat, Oct 25
Logo
6:10 am - 3:07 pmORD-YWG
8h 57m1 stop
Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
$232
Find Deal
Wed, Dec 10 - Fri, Dec 12
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
$379United Airlines
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Thu, Oct 2 - Sun, Oct 5
Porter Airlines Logo
9:35 am - 6:05 pmMDW-YWG
8h 30m1 stop
Porter Airlines Logo
7:00 pm - 8:39 amYWG-MDW
13h 39m1 stop
$379Porter Airlines
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Thu, Oct 2 - Sun, Oct 5
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
$415United Airlines
Find Deal
Thu, Oct 16 - Fri, Oct 24
Delta Logo
6:08 am - 11:30 amORD-YWG
5h 22m1 stop
Delta Logo
8:45 am - 8:23 pmYWG-ORD
11h 38m2 stops
$420Delta
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Wed, Oct 22 - Sat, Oct 25
Delta Logo
9:35 am - 8:11 pmMDW-YWG
10h 36m2 stops
Delta Logo
8:35 am - 1:03 pmYWG-MDW
4h 28m1 stop
$420Delta
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Thu, Oct 2 - Sun, Oct 5
Porter Airlines Logo
4:15 pm - 11:13 amMDW-YWG
18h 58m2 stops
Porter Airlines Logo
4:25 pm - 11:50 amYWG-MDW
19h 25m2 stops
$715Porter Airlines
Find Deal
Wed, Dec 10 - Fri, Dec 12

Porter Airlines flights from Illinois to Winnipeg

Our best Porter Airlines deals on Illinois to Winnipeg flight tickets
Porter Airlines
Oct 2
MDW9:35 amChicago Midway
8h 30m
1 stop
YWG6:05 pmWinnipeg
Oct 5
YWG7:00 pmWinnipeg
13h 39m
1 stop
MDW8:39 amChicago Midway
$379
Find similar
Porter Airlines
Dec 10
MDW4:15 pmChicago Midway
18h 58m
2 stops
YWG11:13 amWinnipeg
Dec 12
YWG4:25 pmWinnipeg
19h 25m
2 stops
MDW11:50 amChicago Midway
$715
Find similar
Porter Airlines
Nov 17
MDW4:15 pmChicago Midway
18h 58m
2 stops
YWG11:13 amWinnipeg
Nov 23
YWG4:25 pmWinnipeg
17h 40m
2 stops
MDW10:05 amChicago Midway
$777
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WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets
WestJet
Oct 16
ORD5:30 pmChicago O'Hare Intl
17h 56m
2 stops
YWG11:26 amWinnipeg
Oct 18
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
$206
Find similar
WestJet
Oct 19
ORD5:30 pmChicago O'Hare Intl
21h 00m
1 stop
YWG2:30 pmWinnipeg
Oct 26
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
$213
Find similar
WestJet
Oct 16
ORD5:30 pmChicago O'Hare Intl
21h 00m
1 stop
YWG2:30 pmWinnipeg
Oct 18
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
$217
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 8, 2025.
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

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-11:26 am

2 stops17h 56m

Winnipeg

Sat 10/18

8:30 am-4:43 pm

1 stop8h 13m

$206

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/19

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Sun 10/26

6:15 am-1:35 pm

1 stop7h 20m

$213

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/22

11:00 am-12:30 am

2 stops13h 30m

Winnipeg

Sat 10/25

8:30 am-4:43 pm

1 stop8h 13m

$215

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 12/10

6:10 am-3:07 pm

1 stop8h 57m

Winnipeg

Fri 12/12

6:15 am-1:35 pm

1 stop7h 20m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/2

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Sun 10/5

2:20 pm-4:51 pm

Nonstop2h 31m

$379

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/2

9:35 am-6:05 pm

1 stop8h 30m

Winnipeg

Sun 10/5

7:00 pm-8:39 am

1 stop13h 39m

$379

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Fri 10/24

2:20 pm-4:51 pm

Nonstop2h 31m

$415

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/22

6:08 am-11:30 am

1 stop5h 22m

Winnipeg

Sat 10/25

8:45 am-8:23 pm

2 stops11h 38m

$420

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/2

9:35 am-8:11 pm

2 stops10h 36m

Winnipeg

Sun 10/5

8:35 am-1:03 pm

1 stop4h 28m

$420

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 12/10

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

Fri 12/12

4:25 pm-11:50 am

2 stops19h 25m

$715

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Winnipeg from

How to get the cheapest flight ticket from Illinois to Winnipeg

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Winnipeg?

In general, May is the cheapest month to fly from Illinois to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $271. If you’re not able to fly to Winnipeg in May, then January is your next best option. Flight prices from Illinois to Winnipeg during January average around $319.

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Friday when prices can be found for as low as $543. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $673.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $543. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $628 on average. Flights to Winnipeg from Illinois at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Illinois to Winnipeg flight route?

Fly from Chicago O'Hare Intl to Winnipeg for the best Illinois - Winnipeg flight prices

What cabin class options are available on Illinois to Winnipeg flights?

There are 2 cabin classes available to choose from on Illinois to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Winnipeg flights?

You could potentially save up to 1% on your flight if you consider stops on a Illinois to Winnipeg flight.

Cheap Illinois to Winnipeg flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Winnipeg

Best Price Found

$268

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Illinois in the past 72 hours is $268. The best round-trip flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $490.
The fastest flight from Illinois to Winnipeg takes 2h 24m
Direct flights go from Illinois to Winnipeg every day.
There is 1 airport near Winnipeg: Winnipeg (YWG)
Search flight deals

  • When did momondo last update prices for flights from Illinois to Winnipeg Airport?

    Prices for flights from Illinois to Winnipeg Airport refresh daily.

  • How many operators does momondo search for flights from Illinois to Winnipeg Airport?

  • How old do you have to be to fly from Illinois to Winnipeg Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Illinois to Winnipeg?

Best airlines flying from Illinois to Winnipeg

Compare and see reviews for airlines that fly from Illinois to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
United AirlinesPriceFrom $415Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Selkirk
Morden
Portage la Prairie

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Winnipeg?

Finding the right flight to Winnipeg from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

Can I find flights from Illinois to Winnipeg with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Winnipeg flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Winnipeg?

momondo helps you find the best flight between Illinois and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Illinois to Winnipeg right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Illinois to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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