Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from $203

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
7:55 pm - 11:35 amYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 10:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$397Multiple Airlines
Mon, Dec 14 - Wed, Dec 16
Multiple Airlines Logo
7:00 am - 11:50 amYWG  Winnipeg-ORD Chicago O'Hare Intl
29h 50m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:20 pm - 10:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$405Multiple Airlines
Mon, Feb 1 - Thu, Feb 4
Multiple Airlines Logo
9:35 pm - 2:30 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
17h 55m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:30 am - 1:10 amORD  Chicago O'Hare Intl-YWG Winnipeg
15h 40m2 stops Atlanta Hartsfield-Jackson Calgary
$407Multiple Airlines
Mon, Dec 14 - Wed, Dec 16
Multiple Airlines Logo
12:40 pm - 11:30 amYWG  Winnipeg-ORD Chicago O'Hare Intl
23h 50m2 stops Ottawa Toronto Island
Multiple Airlines Logo
6:20 pm - 10:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$413Multiple Airlines
Tue, Jan 19 - Fri, Jan 22
Air Canada Logo
8:15 am - 1:13 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
5h 58m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 11:09 amORD  Chicago O'Hare Intl-YWG Winnipeg
13h 19m1 stop Toronto Pearson Intl
$597Air Canada
Tue, Jan 26 - Fri, Jan 29
Air Canada Logo
8:15 am - 3:38 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
8h 23m1 stop Toronto Pearson Intl
Air Canada Logo
9:35 am - 1:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 48mnonstop
$670Air Canada
Mon, Dec 14 - Wed, Dec 16
United Airlines Logo
3:15 pm - 5:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 47mnonstop
United Airlines Logo
10:00 am - 1:52 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 52mnonstop
$679United Airlines
Thu, Dec 17 - Sun, Dec 20
United Airlines Logo
3:15 pm - 5:00 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
9:35 am - 1:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 48mnonstop
$680United Airlines
Fri, Dec 4 - Sun, Dec 6
United Airlines Logo
8:00 am - 9:31 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 31mnonstop
United Airlines Logo
3:35 pm - 7:26 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 51mnonstop
$680United Airlines
Thu, Feb 25 - Sun, Feb 28
Air Canada Logo
6:15 am - 11:57 amYWG  Winnipeg-ORD Chicago O'Hare Intl
6h 42m1 stop Toronto Pearson Intl
Air Canada Logo
9:35 am - 1:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 48mnonstop
$688Air Canada
Thu, Nov 12 - Tue, Nov 17

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
Apr 26
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 3
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$464
WestJet
Nov 12
YWG9:35 pmWinnipeg
13h 50m
2 stops
ORD10:25 amChicago O'Hare Intl
Nov 17
ORD10:32 amChicago O'Hare Intl
29h 53m
2 stops
YWG5:25 pmWinnipeg
$831

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

Our best United Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
United Airlines
Nov 12
YWG3:15 pmWinnipeg
2h 35m
ORD4:50 pmChicago O'Hare Intl
Nov 17
ORD9:35 amChicago O'Hare Intl
2h 48m
YWG1:23 pmWinnipeg
$865
United Airlines
Nov 12
YWG3:15 pmWinnipeg
2h 35m
ORD4:50 pmChicago O'Hare Intl
Nov 17
ORD9:35 amChicago O'Hare Intl
2h 48m
YWG1:23 pmWinnipeg
$910
United Airlines
Nov 12
YWG3:15 pmWinnipeg
2h 35m
ORD4:50 pmChicago O'Hare Intl
Nov 17
ORD9:35 amChicago O'Hare Intl
2h 48m
YWG1:23 pmWinnipeg
$911

momondo Fare Finder

 
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

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:55 pm-11:35 am

1 stop16h 40m

Chicago O'Hare Intl

Wed 12/16

6:20 pm-10:15 am

1 stop14h 55m

$397

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 2/1

7:00 am-11:50 am

1 stop29h 50m

Chicago O'Hare Intl

Thu 2/4

6:20 pm-10:15 am

1 stop14h 55m

$405

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

9:35 pm-2:30 pm

2 stops17h 55m

Chicago O'Hare Intl

Wed 12/16

8:30 am-1:10 am

2 stops15h 40m

$407

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/19

12:40 pm-11:30 am

2 stops23h 50m

Chicago O'Hare Intl

Fri 1/22

6:20 pm-10:15 am

1 stop14h 55m

$413

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/26

8:15 am-1:13 pm

1 stop5h 58m

Chicago O'Hare Intl

Fri 1/29

8:50 pm-11:09 am

1 stop13h 19m

$597

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

8:15 am-3:38 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 12/16

9:35 am-1:23 pm

Nonstop2h 48m

$670

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/17

3:15 pm-5:02 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sun 12/20

10:00 am-1:52 pm

Nonstop2h 52m

$679

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/4

3:15 pm-5:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sun 12/6

9:35 am-1:23 pm

Nonstop2h 48m

$680
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 2/25

8:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 2/28

3:35 pm-7:26 pm

Nonstop2h 51m

$680

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/12

6:15 am-11:57 am

1 stop6h 42m

Chicago O'Hare Intl

Tue 11/17

9:35 am-1:23 pm

Nonstop2h 48m

$688

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?

Prices are currently low for flights on this route.

Typical prices usually range from $504 to $662.
The lowest price recently found on this route was $405.

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

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $515.

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 $619. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday 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 $728.

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 in the morning is the least expensive time of day to depart. momondo users have found prices as low as $671 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $768. 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 37% 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

$203

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 $203. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $397.
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 $517Free CancellationRating
7.3
10,460 reviews
Search United Airlines flights
Air CanadaPriceFrom $629Free CancellationRating
7.1
11,835 reviews
Search Air Canada flights

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

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 1 time per week, with 10,460 momondo users rating the airline 7.3/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was $517 (round-trip), much lower than the average airfare cost of $702 for United Airlines flights on this route.

  • Air Canada Flights From Winnipeg to Chicago O'Hare Intl Airport

    Another popular option for Winnipeg to Chicago O'Hare Intl Airport flights is Air Canada (7.1/10, 11,835 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 2 times per week, with deals starting from $629 round-trip and rising to an average price of around $1,130.

Traveling to a place near Chicago?

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

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
Mon 11/30
Mon 12/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago