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Cheap flights from Winnipeg to Chicago from $121

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 10/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Logo
9:00 am - 12:10 amYWG-ORD
15h 10m1 stop
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$227
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Thu, Sep 11 - Sat, Sep 20
WestJet Logo
7:50 am - 1:35 pmYWG-ORD
29h 45m1 stop
WestJet Logo
2:20 pm - 12:41 amORD-YWG
10h 21m1 stop
$228WestJet
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Thu, Nov 6 - Mon, Nov 10
Logo
8:15 pm - 4:45 pmYWG-ORD
20h 30m2 stops
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$233
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Fri, Sep 12 - Sat, Sep 20
Logo
9:05 pm - 3:50 pmYWG-ORD
18h 45m2 stops
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$238
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Thu, Sep 11 - Sat, Sep 20
Logo
9:05 pm - 10:31 amYWG-ORD
13h 26m2 stops
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$240
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Wed, Sep 10 - Sat, Sep 20
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
$334United Airlines
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Thu, Sep 18 - Sun, Sep 21
Porter Airlines Logo
12:10 pm - 10:05 amYWG-MDW
21h 55m1 stop
Porter Airlines Logo
4:15 pm - 11:13 amMDW-YWG
18h 58m2 stops
$353Porter Airlines
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Sat, Nov 8 - Tue, Nov 11
Delta Logo
12:43 pm - 5:37 pmYWG-MDW
4h 54m1 stop
Delta Logo
7:15 pm - 11:27 pmMDW-YWG
4h 12m1 stop
$358Delta
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Wed, Sep 10 - Tue, Sep 16
Delta Logo
12:43 pm - 5:37 pmYWG-MDW
4h 54m1 stop
Delta Logo
12:43 pm - 11:27 pmMDW-YWG
10h 44m2 stops
$380Delta
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Wed, Sep 10 - Tue, Sep 16
Porter Airlines Logo
4:25 pm - 3:20 pmYWG-MDW
22h 55m2 stops
Porter Airlines Logo
4:15 pm - 11:13 amMDW-YWG
18h 58m2 stops
$572Porter Airlines
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Thu, Nov 6 - Mon, Nov 10

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
Sep 18
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Sep 21
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
$334
Find similar
United Airlines
Aug 29
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Sep 1
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
$698
Find similar
United Airlines
Aug 29
YWG4:25 pmWinnipeg
6h 17m
1 stop
ORD10:42 pmChicago O'Hare Intl
Sep 1
ORD9:17 pmChicago O'Hare Intl
15h 52m
1 stop
YWG1:09 pmWinnipeg
$704
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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Nov 6
YWG7:50 amWinnipeg
29h 45m
1 stop
ORD1:35 pmChicago O'Hare Intl
Nov 10
ORD2:20 pmChicago O'Hare Intl
10h 21m
1 stop
YWG12:41 amWinnipeg
$228
Find similar
WestJet
Oct 16
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 20
ORD5:30 pmChicago O'Hare Intl
18h 11m
1 stop
YWG11:41 amWinnipeg
$245
Find similar
WestJet
Sep 23
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 25
ORD5:30 pmChicago O'Hare Intl
17h 56m
2 stops
YWG11:26 amWinnipeg
$251
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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 August 21, 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

Thu 9/11

9:00 am-12:10 am

1 stop15h 10m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 11/6

7:50 am-1:35 pm

1 stop29h 45m

Chicago O'Hare Intl

Mon 11/10

2:20 pm-12:41 am

1 stop10h 21m

$228

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/12

8:15 pm-4:45 pm

2 stops20h 30m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$233

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/11

9:05 pm-3:50 pm

2 stops18h 45m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$238

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/10

9:05 pm-10:31 am

2 stops13h 26m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$240

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/18

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

7:54 pm-10:33 pm

Nonstop2h 39m

$334

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 11/8

12:10 pm-10:05 am

1 stop21h 55m

Chicago Midway

Tue 11/11

4:15 pm-11:13 am

2 stops18h 58m

$353

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 9/10

12:43 pm-5:37 pm

1 stop4h 54m

Chicago Midway

Tue 9/16

7:15 pm-11:27 pm

1 stop4h 12m

$358

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 9/10

12:43 pm-5:37 pm

1 stop4h 54m

Chicago Midway

Tue 9/16

12:43 pm-11:27 pm

2 stops10h 44m

$380

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 11/6

4:25 pm-3:20 pm

2 stops22h 55m

Chicago Midway

Mon 11/10

4:15 pm-11:13 am

2 stops18h 58m

$572

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 September is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $408. 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 $408.

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 $489. 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 $828.

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 $622.

What is the cheapest Winnipeg to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $448 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Winnipeg for as low as $244 on momondo.

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?

As of August 2025, prices for Winnipeg to Chicago flights are approximately 16% 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

$358

Fastest flight time

2h 31m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $358. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $366.
The fastest flight from Winnipeg to Chicago takes 2h 31m
Direct flights go from Winnipeg to Chicago every day.
There is 1 airport near Chicago: 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 31m.

  • 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
8,930 reviews
Search United Airlines flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $199 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $487 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 10,000 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $645, with deals from around $230 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

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
Lansing
Portage
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.

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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