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Cheap flights from Winnipeg to Chicago from $146

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 Chicago departing on 12/6. 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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Cheap round-trip flights

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Multiple Airlines Logo
6:15 am - 10:23 pmYWG-ORD
16h 08m2 stops
Multiple Airlines Logo
4:45 pm - 3:09 pmORD-YWG
22h 24m1 stop
$198Multiple Airlines
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Tue, Feb 17 - Tue, Feb 24
Multiple Airlines Logo
7:30 am - 10:12 pmYWG-MDW
14h 42m1 stop
Multiple Airlines Logo
6:15 am - 12:41 amMDW-YWG
18h 26m2 stops
$227Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
7:30 am - 10:24 pmYWG-ORD
14h 54m1 stop
Multiple Airlines Logo
6:11 am - 12:41 amORD-YWG
18h 30m2 stops
$227Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:40 pmORD-YWG
8h 20m1 stop
$237WestJet
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Mon, Feb 9 - Mon, Feb 16
Multiple Airlines Logo
7:30 am - 11:54 amYWG-ORD
28h 24m1 stop
Multiple Airlines Logo
7:10 am - 6:03 pmORD-YWG
10h 53m1 stop
$242Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
7:30 am - 10:12 pmYWG-MDW
14h 42m1 stop
Multiple Airlines Logo
6:15 am - 12:43 amMDW-YWG
18h 28m1 stop
$258Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
6:15 am - 10:46 pmYWG-ORD
16h 31m2 stops
Multiple Airlines Logo
2:20 pm - 10:40 pmORD-YWG
8h 20m1 stop
$268Multiple Airlines
Find Deal
Mon, Feb 9 - Mon, Feb 16
WestJet Logo
6:55 pm - 4:43 pmYWG-ORD
21h 48m1 stop
WestJet Logo
5:30 pm - 9:30 pmORD-YWG
28h 00m1 stop
$298WestJet
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Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:08 amORD-YWG
19h 48m1 stop
$317WestJet
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Mon, Dec 29 - Mon, Jan 5
Multiple Airlines Logo
12:55 pm - 12:09 amYWG-ORD
35h 14m3 stops
Multiple Airlines Logo
12:09 pm - 6:06 pmORD-YWG
29h 57m3 stops
$327Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Feb 9
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Feb 16
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$237
Find similar
WestJet
Apr 25
YWG6:55 pmWinnipeg
21h 48m
1 stop
ORD4:43 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
28h 00m
1 stop
YWG9:30 pmWinnipeg
$298
Find similar
WestJet
Dec 29
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Jan 5
ORD2:20 pmChicago O'Hare Intl
19h 48m
1 stop
YWG10:08 amWinnipeg
$317
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Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
Mar 3
YWG6:00 amWinnipeg
6h 33m
1 stop
ORD12:33 pmChicago O'Hare Intl
Mar 8
ORD8:00 amChicago O'Hare Intl
7h 30m
1 stop
YWG3:30 pmWinnipeg
$473
Find similar
Porter Airlines
Nov 17
YWG12:10 pmWinnipeg
7h 10m
1 stop
ORD7:20 pmChicago O'Hare Intl
Nov 24
ORD6:34 pmChicago O'Hare Intl
20h 56m
1 stop
YWG3:30 pmWinnipeg
$1,099
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momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago 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 November 16, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 2/17

6:15 am-10:23 pm

2 stops16h 08m

Chicago O'Hare Intl

Tue 2/24

4:45 pm-3:09 pm

1 stop22h 24m

$198

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 12/12

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

Mon 12/15

6:15 am-12:41 am

2 stops18h 26m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/12

7:30 am-10:24 pm

1 stop14h 54m

Chicago O'Hare Intl

Mon 12/15

6:11 am-12:41 am

2 stops18h 30m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 2/9

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 2/16

2:20 pm-10:40 pm

1 stop8h 20m

$237

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/12

7:30 am-11:54 am

1 stop28h 24m

Chicago O'Hare Intl

Mon 12/15

7:10 am-6:03 pm

1 stop10h 53m

$242

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 12/12

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

Mon 12/15

6:15 am-12:43 am

1 stop18h 28m

$258

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 2/9

6:15 am-10:46 pm

2 stops16h 31m

Chicago O'Hare Intl

Mon 2/16

2:20 pm-10:40 pm

1 stop8h 20m

$268

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

6:55 pm-4:43 pm

1 stop21h 48m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-9:30 pm

1 stop28h 00m

$298

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 12/29

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 1/5

2:20 pm-10:08 am

1 stop19h 48m

$317

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 12/12

12:55 pm-12:09 am

3 stops35h 14m

Chicago O'Hare Intl

Mon 12/15

12:09 pm-6:06 pm

3 stops29h 57m

$327

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 Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $354. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Winnipeg to Chicago during October average around $358.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $556. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $814.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Winnipeg to Chicago during this time can be as low as $440. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $621.

What is the cheapest Winnipeg to Chicago flight route?

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

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

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

No. A direct flight is the cheapest option for a flight between Winnipeg to Chicago.

How have Winnipeg to Chicago flight prices changed over time?

When to book flights from Winnipeg to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

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

Best Price Found

$268

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $268. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $482.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 4h 23m.

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

    Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

  • What is the most popular airline from Winnipeg to Chicago?

Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $199Free CancellationRating
7.4
9,013 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $199 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $471 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.

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

momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Chicago from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

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Tue 12/16
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport