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Cheap flights from Winnipeg to Illinois from $160

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Illinois departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$212WestJet
Find Deal
mié., sep. 24 - sáb., sep. 27
WestJet Logo
6:30 am - 4:44 pmYWG-ORD
10h 14m2 stops
WestJet Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$228WestJet
Find Deal
mié., ago. 27 - mié., sep. 3
WestJet Logo
6:30 am - 4:43 pmYWG-ORD
10h 13m2 stops
WestJet Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$230WestJet
Find Deal
mié., sep. 24 - sáb., sep. 27
Logo
7:00 pm - 9:51 amYWG-ORD
14h 51m2 stops
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$293
Find Deal
sáb., sep. 13 - sáb., sep. 20
Logo
9:10 am - 9:58 pmYWG-ORD
12h 48m1 stop
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$309
Find Deal
sáb., sep. 13 - sáb., sep. 20
Air Canada Logo
12:00 pm - 8:11 pmYWG-ORD
8h 11m1 stop
Air Canada Logo
10:40 am - 6:59 pmORD-YWG
8h 19m1 stop
$324Air Canada
Find Deal
vie., sep. 12 - vie., sep. 19
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$336United Airlines
Find Deal
jue., sep. 18 - dom., sep. 21
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$337United Airlines
Find Deal
vie., sep. 12 - vie., sep. 19
Delta Logo
6:40 am - 12:28 pmYWG-MDW
5h 48m2 stops
Delta Logo
1:08 pm - 11:27 pmMDW-YWG
10h 19m2 stops
$359Delta
Find Deal
sáb., sep. 13 - sáb., sep. 20
Delta Logo
12:43 pm - 5:37 pmYWG-MDW
4h 54m1 stop
Delta Logo
6:00 am - 4:51 pmMDW-YWG
10h 51m2 stops
$374Delta
Find Deal
mié., ago. 27 - mié., sep. 3

Air Canada flights from Winnipeg to Illinois

Our best Air Canada deals on Winnipeg to Illinois flight tickets
Air Canada
Sep 12
YWG12:00 pmWinnipeg
8h 11m
1 stop
ORD8:11 pmChicago O'Hare Intl
Sep 19
ORD10:40 amChicago O'Hare Intl
8h 19m
1 stop
YWG6:59 pmWinnipeg
$324
Find similar
Air Canada
Aug 14
YWG8:10 pmWinnipeg
13h 42m
2 stops
ORD9:52 amChicago O'Hare Intl
Aug 16
ORD10:40 amChicago O'Hare Intl
8h 19m
1 stop
YWG6:59 pmWinnipeg
$427
Find similar
Air Canada
Aug 8
YWG12:00 pmWinnipeg
6h 46m
1 stop
ORD6:46 pmChicago O'Hare Intl
Aug 11
ORD7:58 pmChicago O'Hare Intl
2h 35m
YWG10:33 pmWinnipeg
$598
Find similar

Delta flights from Winnipeg to Illinois

Our best Delta deals on Winnipeg to Illinois flight tickets
Delta
Sep 13
YWG6:40 amWinnipeg
5h 48m
2 stops
MDW12:28 pmChicago Midway
Sep 20
MDW1:08 pmChicago Midway
10h 19m
2 stops
YWG11:27 pmWinnipeg
$359
Find similar
Delta
Aug 27
YWG12:43 pmWinnipeg
4h 54m
1 stop
MDW5:37 pmChicago Midway
Sep 3
MDW6:00 amChicago Midway
10h 51m
2 stops
YWG4:51 pmWinnipeg
$374
Find similar
Delta
Sep 13
YWG6:40 amWinnipeg
5h 48m
2 stops
MDW12:28 pmChicago Midway
Sep 20
MDW9:20 amChicago Midway
7h 30m
1 stop
YWG4:50 pmWinnipeg
$381
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Illinois 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 julio 31, 2025.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mié. 9/24

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

sáb. 9/27

1:40 pm-9:25 pm

1 stop7h 45m

$212

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mié. 8/27

6:30 am-4:44 pm

2 stops10h 14m

Chicago O'Hare Intl

mié. 9/3

1:40 pm-9:25 pm

1 stop7h 45m

$228

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mié. 9/24

6:30 am-4:43 pm

2 stops10h 13m

Chicago O'Hare Intl

sáb. 9/27

1:40 pm-9:25 pm

1 stop7h 45m

$230

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 9/13

7:00 pm-9:51 am

2 stops14h 51m

Chicago O'Hare Intl

sáb. 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$293

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 9/13

9:10 am-9:58 pm

1 stop12h 48m

Chicago O'Hare Intl

sáb. 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$309

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 9/12

12:00 pm-8:11 pm

1 stop8h 11m

Chicago O'Hare Intl

vie. 9/19

10:40 am-6:59 pm

1 stop8h 19m

$324

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 9/18

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

dom. 9/21

1:01 pm-3:31 pm

Nonstop2h 30m

$336

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 9/12

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

vie. 9/19

1:01 pm-3:31 pm

Nonstop2h 30m

$337

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

sáb. 9/20

1:08 pm-11:27 pm

2 stops10h 19m

$359

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mié. 8/27

12:43 pm-5:37 pm

1 stop4h 54m

Chicago Midway

mié. 9/3

6:00 am-4:51 pm

2 stops10h 51m

$374

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 Illinois from

How to get the cheapest flight ticket from Winnipeg to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Winnipeg is in June. Flight prices, which tend to average around $411, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of June, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $418.

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

The cheapest day to depart from Winnipeg to Illinois is on a Friday when prices can be found for as low as $501. Flights from Winnipeg to Illinois on a Sunday will generally be more expensive and average around $836. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Winnipeg to Illinois during this time can be as low as $440. Flights at noon are often more expensive with an average ticket price of $628.

What is the cheapest Winnipeg to Illinois flight route?

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

How far in advance should I book a flight to Illinois?

You are more likely to see cheaper flights to Illinois from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $453 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Winnipeg for as low as $244 on momondo.

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

There are 4 cabin classes available to choose from on Winnipeg to Illinois 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 Winnipeg to Illinois flights?

You could potentially save up to 17% on your flight if you consider stops on a Winnipeg to Illinois flight.

Cheap Winnipeg to Illinois flight deals and tips

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

Best Price Found

$160

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

3 airports
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $160. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $212.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois every day.
There are 3 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL)
Search flight deals

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

    Prices for flights from Winnipeg Airport to Illinois refresh daily.

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

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

    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 Winnipeg Airport to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Winnipeg to Illinois

Compare and see reviews for airlines that fly from Winnipeg to Illinois with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $199Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights

Why use momondo?

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

It is quick and easy to find Winnipeg to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

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

Yes. momondo enables you to select and highlight flights to Illinois from Winnipeg with this policy.

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

Once all potential Winnipeg to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Winnipeg to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.

An easier way to manage your Illinois trip

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