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Cheap flights from Winnipeg to Illinois from $182

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 10/29. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
$322WestJet
Sun, Oct 25 - Thu, Oct 29
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$334WestJet
Fri, Sep 25 - Mon, Sep 28
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 10:10 pm
ORD
-
YWG
28h 40m
1 stop
$359WestJet
Fri, Sep 25 - Mon, Sep 28
Multiple Airlines Logo
11:40 am - 9:35 pm
YWG
-
ORD
9h 55m
2 stops
Multiple Airlines Logo
3:20 pm - 9:45 am
ORD
-
YWG
18h 25m
1 stop
$367Multiple Airlines
Fri, Sep 25 - Mon, Sep 28
WestJet Logo
9:00 pm - 1:35 pm
YWG
-
ORD
16h 35m
1 stop
WestJet Logo
2:20 pm - 11:55 pm
ORD
-
YWG
9h 35m
1 stop
$379WestJet
Sat, Oct 31 - Fri, Nov 6
WestJet Logo
9:00 pm - 1:35 pm
YWG
-
ORD
16h 35m
1 stop
WestJet Logo
2:20 pm - 11:55 pm
ORD
-
YWG
9h 35m
1 stop
$383WestJet
Sat, Oct 31 - Fri, Nov 6
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
11:45 am - 10:43 am
ORD
-
YWG
22h 58m
2 stops
$393Multiple Airlines
Fri, Sep 25 - Sun, Sep 27
Delta Logo
5:42 pm - 11:26 pm
YWG
-
STL
5h 44m
1 stop
Delta Logo
11:13 am - 3:08 pm
STL
-
YWG
3h 55m
1 stop
$432Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
6:35 am - 10:10 pm
YWG
-
MDW
15h 35m
2 stops
Delta Logo
6:00 am - 11:34 pm
MDW
-
YWG
17h 34m
2 stops
$453Delta
Sat, Oct 31 - Wed, Nov 4
Air Canada Logo
5:00 am - 6:42 pm
YWG
-
STL
13h 42m
2 stops
Air Canada Logo
8:55 am - 4:20 pm
STL
-
YWG
7h 25m
1 stop
$518Air Canada
Wed, Aug 26 - Sat, Aug 29

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WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets
WestJet
Oct 25
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Oct 29
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$322
WestJet
Sep 25
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 28
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$334
WestJet
Sep 25
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 28
ORD5:30 pmChicago O'Hare Intl
28h 40m
1 stop
YWG10:10 pmWinnipeg
$359

Delta flights from Winnipeg to Illinois

Our best Delta deals on Winnipeg to Illinois flight tickets
Delta
Aug 26
YWG3:58 pmWinnipeg
7h 28m
1 stop
STL11:26 pmLambert-St Louis
Aug 29
STL6:20 amLambert-St Louis
8h 48m
1 stop
YWG3:08 pmWinnipeg
$432
Delta
Oct 31
YWG6:35 amWinnipeg
15h 35m
2 stops
MDW10:10 pmChicago Midway
Nov 4
MDW6:00 amChicago Midway
17h 34m
2 stops
YWG11:34 pmWinnipeg
$453
Delta
Oct 31
YWG6:35 amWinnipeg
15h 35m
2 stops
MDW10:10 pmChicago Midway
Nov 4
MDW6:00 amChicago Midway
14h 16m
2 stops
YWG8:16 pmWinnipeg
$486

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 June 9, 2026.
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

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/25

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Thu 10/29

2:20 pm-10:40 pm

1 stop8h 20m

$322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-12:55 am

1 stop7h 25m

$334

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-10:10 pm

1 stop28h 40m

$359

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

11:40 am-9:35 pm

2 stops9h 55m

Chicago O'Hare Intl

Mon 9/28

3:20 pm-9:45 am

1 stop18h 25m

$367

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/31

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Fri 11/6

2:20 pm-11:55 pm

1 stop9h 35m

$379

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/31

9:00 pm-1:35 pm

1 stop16h 35m

Chicago O'Hare Intl

Fri 11/6

2:20 pm-11:55 pm

1 stop9h 35m

$383

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/27

11:45 am-10:43 am

2 stops22h 58m

$393
Quickest round-trip

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Wed 8/26

5:42 pm-11:26 pm

1 stop5h 44m

Lambert-St Louis

Sat 8/29

11:13 am-3:08 pm

1 stop3h 55m

$432

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 10/31

6:35 am-10:10 pm

2 stops15h 35m

Chicago Midway

Wed 11/4

6:00 am-11:34 pm

2 stops17h 34m

$453

WinnipegSt. Louis

YWG - STL

YWGSTL

Winnipeg

Wed 8/26

5:00 am-6:42 pm

2 stops13h 42m

Lambert-St Louis

Sat 8/29

8:55 am-4:20 pm

1 stop7h 25m

$518

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 October. Flight prices, which tend to average around $80, 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 October, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $127.

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

The cheapest day to depart from Winnipeg to Illinois is on a Saturday when prices can be found for as low as $599. Flights from Winnipeg to Illinois on a Sunday will generally be more expensive and average around $786. 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 morning. Flights from Winnipeg to Illinois during this time can be as low as $610. Flights at noon are often more expensive with an average ticket price of $647.

What is the cheapest Winnipeg to Illinois flight route?

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

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 15% 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

$274

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Winnipeg in the past 72 hours is $274. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $611.
The fastest flight from Winnipeg to Illinois takes 2h 21m
Direct flights go from Winnipeg to Illinois every day.
There are 98 airports in Illinois. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Winnipeg to Illinois

  • 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
9,796 reviews
Search United Airlines 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.

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Find better results for your trip to Illinois

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