Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from $192

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 10/21. 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.
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
$273WestJet
Fri, Oct 2 - Sun, Oct 4
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
$277WestJet
Thu, Oct 15 - Sun, Oct 18
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
$303WestJet
Fri, Oct 2 - Mon, Oct 5
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
$310WestJet
Fri, Sep 18 - Fri, Sep 25
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
$311WestJet
Sat, Sep 5 - Fri, Sep 11
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
$315WestJet
Sat, Sep 5 - Thu, Sep 10
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
$318WestJet
Tue, Sep 1 - Tue, Sep 8
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
$345WestJet
Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
7:45 am - 12:55 am
ORD
-
YWG
17h 10m
2 stops
$346Multiple Airlines
Sat, Sep 5 - Fri, Sep 11
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
$347WestJet
Thu, Sep 10 - Tue, Sep 15

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
WestJet
Oct 2
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 4
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$273
WestJet
Oct 15
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 18
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$277
WestJet
Oct 2
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 5
ORD5:30 pmChicago O'Hare Intl
17h 40m
1 stop
YWG11:10 amWinnipeg
$303

Porter Airlines flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Porter Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Porter Airlines
Sep 5
YWG12:15 pmWinnipeg
7h 14m
1 stop
ORD7:29 pmChicago O'Hare Intl
Sep 12
ORD8:03 amChicago O'Hare Intl
7h 16m
1 stop
YWG3:19 pmWinnipeg
$466
Porter Airlines
Jul 26
YWG8:50 pmWinnipeg
19h 29m
1 stop
ORD4:19 pmChicago O'Hare Intl
Aug 5
ORD8:09 amChicago O'Hare Intl
7h 10m
1 stop
YWG3:19 pmWinnipeg
$868
Porter Airlines
Jul 25
YWG12:15 pmWinnipeg
7h 25m
1 stop
ORD7:40 pmChicago O'Hare Intl
Jul 27
ORD8:29 pmChicago O'Hare Intl
23h 25m
1 stop
YWG7:54 pmWinnipeg
$874

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago O'Hare Intl Airport 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 July 23, 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport 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 10/2

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 10/4

5:30 pm-12:55 am

1 stop7h 25m

$273

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/15

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 10/18

5:30 pm-12:55 am

1 stop7h 25m

$277

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/2

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/5

5:30 pm-11:10 am

1 stop17h 40m

$303

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/18

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 9/25

5:30 pm-12:55 am

1 stop7h 25m

$310

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-12:55 am

1 stop7h 25m

$311

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 9/10

5:30 pm-12:55 am

1 stop7h 25m

$315

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/1

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/8

5:30 pm-12:55 am

1 stop7h 25m

$318

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 8/27

7:00 am-4:40 pm

2 stops9h 40m

Chicago O'Hare Intl

Tue 9/1

5:30 pm-12:55 am

1 stop7h 25m

$345

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 9/11

7:45 am-12:55 am

2 stops17h 10m

$346

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/15

5:30 pm-12:55 am

1 stop7h 25m

$347

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $483.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $605. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $786.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Winnipeg at noon is the least expensive time of day to depart. momondo users have found prices as low as $648 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $648. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Winnipeg to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Winnipeg to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 6% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Winnipeg to Chicago O'Hare Intl Airport

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

Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport

Best Price Found

$325

Fastest flight time

2h 21m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $325. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $539.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 21m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago O'Hare Intl Airport

  • How far is Winnipeg to Chicago O'Hare Intl by plane?

    There are 702.3 mi between Winnipeg and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 21m.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Winnipeg to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?

Best airlines flying from Winnipeg to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $335Free CancellationRating
7.4
10,024 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with 10,024 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was $335 (round-trip), much lower than the average airfare cost of $546 for United Airlines flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Merrillville
Rockford
Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

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?

Flights from Winnipeg to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Winnipeg to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Winnipeg and alert you when they change.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 8/22
Sat 8/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago