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Cheap flights from Winnipeg to Chicago from $166

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 9/21. 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 Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:05 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
16h 55m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 12:55 amMDW  Chicago Midway-YWG Winnipeg
13h 10m1 stop Toronto Island
$327Multiple Airlines
Wed, Sep 23 - Sun, Oct 4
Multiple Airlines Logo
11:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 9:45 amMDW  Chicago Midway-YWG Winnipeg
18h 25m1 stop Toronto Island
$332Multiple Airlines
Wed, Sep 23 - Sun, Oct 4
Multiple Airlines Logo
11:15 am - 7:48 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
8h 33m2 stops Montreal St Hubert Toronto Pearson Intl
Multiple Airlines Logo
9:50 am - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
15h 05m1 stop Toronto Pearson Intl
$360Multiple Airlines
Fri, Sep 18 - Fri, Sep 25
Multiple Airlines Logo
6:55 pm - 11:05 amYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 10m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:10 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
15h 05m1 stop Toronto Island
$362Multiple Airlines
Sun, Oct 25 - Sun, Nov 1
Multiple Airlines Logo
6:15 am - 7:48 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
13h 33m1 stop Toronto Pearson Intl
Multiple Airlines Logo
2:20 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
10h 35m1 stop Toronto Pearson Intl
$362Multiple Airlines
Fri, Sep 18 - Fri, Sep 25
WestJet Logo
7:10 pm - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
21h 30m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$364WestJet
Fri, Aug 28 - Mon, Aug 31
WestJet Logo
9:05 pm - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
19h 35m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$368WestJet
Fri, Aug 28 - Tue, Sep 1
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 3:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
21h 55m1 stop Calgary
$373WestJet
Wed, Sep 2 - Thu, Sep 3
United Airlines Logo
5:10 am - 6:30 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
13h 20m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
6:03 pm - 2:22 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 19m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$667United Airlines
Wed, Oct 7 - Wed, Oct 14
United Airlines Logo
2:00 pm - 4:35 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 35mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 39mnonstop
$684United Airlines
Sat, Oct 10 - Sat, Oct 17

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Aug 28
YWG7:10 pmWinnipeg
21h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
Aug 31
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$364
WestJet
Aug 28
YWG9:05 pmWinnipeg
19h 35m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 1
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$368
WestJet
Sep 2
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 3
ORD5:30 pmChicago O'Hare Intl
21h 55m
1 stop
YWG3:25 pmWinnipeg
$373

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
Aug 19
YWG8:45 amWinnipeg
14h 01m
1 stop
ORD10:46 pmChicago O'Hare Intl
Aug 21
ORD9:15 amChicago O'Hare Intl
2h 37m
YWG11:52 amWinnipeg
$809
United Airlines
Aug 19
YWG8:45 amWinnipeg
11h 36m
1 stop
ORD8:21 pmChicago O'Hare Intl
Aug 23
ORD9:15 amChicago O'Hare Intl
2h 37m
YWG11:52 amWinnipeg
$810
United Airlines
Aug 19
YWG8:45 amWinnipeg
15h 14m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 24
ORD9:15 amChicago O'Hare Intl
2h 37m
YWG11:52 amWinnipeg
$811

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 7, 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 Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 9/23

6:05 pm-11:00 am

1 stop16h 55m

Chicago Midway

Sun 10/4

11:45 am-12:55 am

1 stop13h 10m

$327

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 9/23

11:15 am-11:00 am

2 stops23h 45m

Chicago Midway

Sun 10/4

3:20 pm-9:45 am

1 stop18h 25m

$332

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 9/18

11:15 am-7:48 pm

2 stops8h 33m

Chicago O'Hare Intl

Fri 9/25

9:50 am-12:55 am

1 stop15h 05m

$360

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 10/25

6:55 pm-11:05 am

1 stop16h 10m

Chicago O'Hare Intl

Sun 11/1

6:10 pm-9:15 am

1 stop15h 05m

$362

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 9/18

6:15 am-7:48 pm

1 stop13h 33m

Chicago O'Hare Intl

Fri 9/25

2:20 pm-12:55 am

1 stop10h 35m

$362

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 8/28

7:10 pm-4:40 pm

1 stop21h 30m

Chicago O'Hare Intl

Mon 8/31

5:30 pm-12:55 am

1 stop7h 25m

$364

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 8/28

9:05 pm-4:40 pm

1 stop19h 35m

Chicago O'Hare Intl

Tue 9/1

5:30 pm-12:55 am

1 stop7h 25m

$368

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 9/2

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 9/3

5:30 pm-3:25 pm

1 stop21h 55m

$373

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 10/7

5:10 am-6:30 pm

2 stops13h 20m

Chicago O'Hare Intl

Wed 10/14

6:03 pm-2:22 pm

2 stops20h 19m

$667
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 10/10

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 10/17

7:54 pm-10:33 pm

Nonstop2h 39m

$684

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?

Prices are currently low for flights on this route.

Typical prices usually range from $465 to $825.
The lowest price recently found on this route was $327.

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 $380. 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 $387.

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 $604. 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 $786.

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 at noon. Flights from Winnipeg to Chicago during this time can be as low as $638. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $659.

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.

How have Winnipeg to Chicago flight prices changed over time?

As of August 2026, prices for Winnipeg to Chicago flights are approximately 113% 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

$389

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 $389. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $545.
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 $335Free CancellationRating
7.4
10,081 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $335 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $657 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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