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Cheap flights from Winnipeg to Chicago from $158

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 4/30. 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 Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
$266WestJet
Fri, May 8 - Fri, May 15
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
$279WestJet
Fri, Jun 5 - Tue, Jun 9
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
$285WestJet
Sun, May 3 - Thu, May 7
WestJet Logo
6:00 am - 4:40 pm
YWG
-
ORD
10h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$297WestJet
Fri, May 22 - Fri, May 29
WestJet Logo
6:00 am - 4:40 pm
YWG
-
ORD
10h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$300WestJet
Fri, May 22 - Fri, May 29
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 11:10 am
ORD
-
YWG
17h 40m
1 stop
$315WestJet
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
11:51 am - 3:25 pm
ORD
-
YWG
27h 34m
2 stops
$321Multiple Airlines
Fri, May 8 - Mon, May 11
Delta Logo
5:20 pm - 9:56 am
YWG
-
MDW
16h 36m
2 stops
Delta Logo
12:53 pm - 2:55 pm
MDW
-
YWG
26h 02m
2 stops
$468Delta
Mon, May 4 - Fri, May 8
Delta Logo
5:20 pm - 10:28 pm
YWG
-
MDW
29h 08m
2 stops
Delta Logo
12:53 pm - 2:55 pm
MDW
-
YWG
26h 02m
2 stops
$484Delta
Fri, May 1 - Fri, May 8
Delta Logo
5:20 pm - 12:07 pm
YWG
-
MDW
18h 47m
2 stops
Delta Logo
2:12 pm - 10:54 am
MDW
-
YWG
20h 42m
1 stop
$496Delta
Mon, May 4 - Wed, May 6

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
May 8
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 15
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$266
WestJet
May 3
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 7
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$285
WestJet
May 22
YWG6:00 amWinnipeg
10h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 29
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$297

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
Mar 31
YWG12:10 pmWinnipeg
7h 07m
1 stop
ORD7:17 pmChicago O'Hare Intl
Apr 1
ORD8:12 amChicago O'Hare Intl
7h 18m
1 stop
YWG3:30 pmWinnipeg
$652
Porter Airlines
Mar 31
YWG12:10 pmWinnipeg
7h 07m
1 stop
ORD7:17 pmChicago O'Hare Intl
Apr 4
ORD8:12 amChicago O'Hare Intl
7h 18m
1 stop
YWG3:30 pmWinnipeg
$677
Porter Airlines
Mar 31
YWG12:10 pmWinnipeg
7h 07m
1 stop
ORD7:17 pmChicago O'Hare Intl
Apr 3
ORD6:40 pmChicago O'Hare Intl
20h 50m
1 stop
YWG3:30 pmWinnipeg
$685

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 March 18, 2026.
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

Cheapest round-trip
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop7h 25m

$266

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 6/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 6/9

5:30 pm-12:55 am

1 stop7h 25m

$279

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 5/3

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-12:55 am

1 stop7h 25m

$285

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/22

6:00 am-4:40 pm

1 stop10h 40m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$297

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/22

6:00 am-4:40 pm

1 stop10h 40m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 4/30

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 5/3

5:30 pm-11:10 am

1 stop17h 40m

$315

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 5/11

11:51 am-3:25 pm

2 stops27h 34m

$321

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 5/4

5:20 pm-9:56 am

2 stops16h 36m

Chicago Midway

Fri 5/8

12:53 pm-2:55 pm

2 stops26h 02m

$468

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/1

5:20 pm-10:28 pm

2 stops29h 08m

Chicago Midway

Fri 5/8

12:53 pm-2:55 pm

2 stops26h 02m

$484

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 5/4

5:20 pm-12:07 pm

2 stops18h 47m

Chicago Midway

Wed 5/6

2:12 pm-10:54 am

1 stop20h 42m

$496

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 $358. 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 Thursday when prices can be found for as low as $504. 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 $797.

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 morning. Flights from Winnipeg to Chicago during this time can be as low as $607. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $612.

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?

You could potentially save up to 23% on your flight if you consider stops on a Winnipeg to Chicago flight.

How have Winnipeg to Chicago flight prices changed over time?

As of March 2026, prices for Winnipeg to Chicago flights are approximately 108% more expensive when compared to flights at the same time last year.

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

$277

Fastest flight time

2h 25m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $277. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $424.
The fastest flight from Winnipeg to Chicago takes 2h 25m
Direct flights go from Winnipeg to Chicago every day.
There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 25m.

  • 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
9,435 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 $517 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
Valparaiso
Schererville
Munster
Crown Point
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.

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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