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Cheap flights from Winnipeg to Chicago from $210

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 6/12. 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
$350WestJet
Fri, Sep 11 - Sun, Sep 13
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$388WestJet
Thu, Sep 17 - Tue, Sep 22
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
2 stops
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$394WestJet
Fri, Sep 11 - Sun, Sep 13
WestJet Logo
9:00 pm - 1:35 pm
YWG
-
ORD
16h 35m
1 stop
WestJet Logo
2:20 pm - 5:05 pm
ORD
-
YWG
26h 45m
1 stop
$402WestJet
Sat, Oct 31 - Fri, Nov 6
Porter Airlines Logo
11:15 am - 9:35 pm
YWG
-
ORD
10h 20m
2 stops
Porter Airlines Logo
11:45 am - 3:19 pm
ORD
-
YWG
27h 34m
1 stop
$406Porter Airlines
Thu, Sep 17 - Sun, Sep 20
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 2:40 pm
ORD
-
YWG
21h 10m
2 stops
$440WestJet
Fri, Sep 4 - Mon, Sep 7
Multiple Airlines Logo
6:00 am - 2:14 pm
YWG
-
ORD
8h 14m
1 stop
Multiple Airlines Logo
2:20 pm - 9:40 pm
ORD
-
YWG
7h 20m
1 stop
$451Multiple Airlines
Sat, Nov 14 - Fri, Nov 20
Multiple Airlines Logo
6:15 am - 2:35 pm
YWG
-
MDW
8h 20m
1 stop
Multiple Airlines Logo
10:25 am - 7:25 pm
MDW
-
YWG
9h 00m
1 stop
$456Multiple Airlines
Fri, Jun 26 - Fri, Jul 3
Delta Logo
6:35 am - 9:45 pm
YWG
-
MDW
15h 10m
2 stops
Delta Logo
6:00 am - 11:34 pm
MDW
-
YWG
17h 34m
2 stops
$506Delta
Tue, Oct 20 - Thu, Oct 22
Porter Airlines Logo
8:50 pm - 9:40 am
YWG
-
MDW
12h 50m
1 stop
Porter Airlines Logo
10:25 am - 11:19 am
MDW
-
YWG
24h 54m
1 stop
$527Porter Airlines
Thu, Jul 2 - Sun, Jul 5

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
Sep 20
YWG5:10 amWinnipeg
6h 50m
1 stop
ORD12:00 pmChicago O'Hare Intl
Sep 26
ORD2:15 pmChicago O'Hare Intl
6h 57m
1 stop
YWG9:12 pmWinnipeg
$551
Air Canada
Jun 23
YWG5:10 amWinnipeg
8h 12m
1 stop
ORD1:22 pmChicago O'Hare Intl
Jun 30
ORD8:00 pmChicago O'Hare Intl
2h 38m
YWG10:38 pmWinnipeg
$557
Air Canada
Jun 23
YWG5:10 amWinnipeg
8h 12m
1 stop
ORD1:22 pmChicago O'Hare Intl
Jun 30
ORD8:00 pmChicago O'Hare Intl
2h 38m
YWG10:38 pmWinnipeg
$558

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Sep 11
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 13
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$350
WestJet
Sep 17
YWG9:05 pmWinnipeg
19h 35m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 22
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$388
WestJet
Sep 11
YWG7:00 amWinnipeg
9h 40m
2 stops
ORD4:40 pmChicago O'Hare Intl
Sep 13
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$394

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 May 31, 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/11

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-12:55 am

1 stop7h 25m

$350

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/17

9:05 pm-4:40 pm

1 stop19h 35m

Chicago O'Hare Intl

Tue 9/22

5:30 pm-12:55 am

1 stop7h 25m

$388

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/11

7:00 am-4:40 pm

2 stops9h 40m

Chicago O'Hare Intl

Sun 9/13

5:30 pm-12:55 am

1 stop7h 25m

$394

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-5:05 pm

1 stop26h 45m

$402

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/17

11:15 am-9:35 pm

2 stops10h 20m

Chicago O'Hare Intl

Sun 9/20

11:45 am-3:19 pm

1 stop27h 34m

$406

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/4

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/7

5:30 pm-2:40 pm

2 stops21h 10m

$440
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 11/14

6:00 am-2:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Fri 11/20

2:20 pm-9:40 pm

1 stop7h 20m

$451

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 6/26

6:15 am-2:35 pm

1 stop8h 20m

Chicago Midway

Fri 7/3

10:25 am-7:25 pm

1 stop9h 00m

$456

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 10/20

6:35 am-9:45 pm

2 stops15h 10m

Chicago Midway

Thu 10/22

6:00 am-11:34 pm

2 stops17h 34m

$506

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 7/2

8:50 pm-9:40 am

1 stop12h 50m

Chicago Midway

Sun 7/5

10:25 am-11:19 am

1 stop24h 54m

$527

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 typical price of a round-trip flight between Winnipeg and Chicago?

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $80. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Winnipeg to Chicago during November average around $127.

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 Saturday when prices can be found for as low as $600. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $781.

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 $610. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $647.

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 15% 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 May 2026, prices for Winnipeg to Chicago flights are approximately 17% 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

$397

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $397. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $613.
The fastest flight from Winnipeg to Chicago takes 2h 21m
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

Frequently asked questions about flying from Winnipeg to Chicago

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 21m.

  • 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
9,768 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 4 United Airlines flights for this route in a normal week, average airfare is usually $546 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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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