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Cheap flights from Winnipeg to Chicago from $216

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
7:00 am - 6:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
35h 25m2 stops Atlanta Hartsfield-Jackson Calgary
$385Multiple Airlines
Wed, Dec 16 - Sat, Jan 9
Multiple Airlines Logo
7:00 am - 7:20 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 20m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
35h 25m2 stops Atlanta Hartsfield-Jackson Calgary
$385Multiple Airlines
Mon, Dec 14 - Sat, Jan 9
Multiple Airlines Logo
7:00 am - 6:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 40m1 stop Atlanta Hartsfield-Jackson
$387Multiple Airlines
Wed, Dec 16 - Wed, Jan 6
Multiple Airlines Logo
7:00 am - 6:37 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 37m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 40m1 stop Atlanta Hartsfield-Jackson
$400Multiple Airlines
Wed, Dec 16 - Fri, Jan 8
Air Canada Logo
9:15 am - 3:38 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
6h 23m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 11:00 amORD  Chicago O'Hare Intl-YWG Winnipeg
21h 05m1 stop Montreal Pierre Elliott Trudeau Intl
$467Air Canada
Thu, Nov 19 - Sun, Nov 22
Air Canada Logo
3:15 pm - 4:50 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
1h 35mnonstop
Air Canada Logo
7:02 am - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 07m1 stop Toronto Pearson Intl
$652Air Canada
Fri, Nov 27 - Wed, Dec 2
Air Canada Logo
6:15 am - 11:57 amYWG  Winnipeg-ORD Chicago O'Hare Intl
5h 42m1 stop Toronto Pearson Intl
Air Canada Logo
9:35 am - 1:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
3h 48mnonstop
$675Air Canada
Thu, Nov 12 - Tue, Nov 17
United Airlines Logo
3:15 pm - 5:02 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
1h 47mnonstop
United Airlines Logo
6:15 pm - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$729United Airlines
Wed, Dec 23 - Tue, Jan 5
United Airlines Logo
4:05 pm - 9:37 amYWG  Winnipeg-ORD Chicago O'Hare Intl
17h 32m2 stops Toronto Pearson Intl Minneapolis St Paul
United Airlines Logo
6:15 pm - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$733United Airlines
Mon, Feb 1 - Mon, Feb 8
United Airlines Logo
12:05 pm - 7:55 amYWG  Winnipeg-ORD Chicago O'Hare Intl
19h 50m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
United Airlines Logo
6:15 pm - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 54m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$738United Airlines
Wed, Dec 23 - Tue, Jan 5

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Air Canada flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Air Canada deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Air Canada
Nov 19
YWG9:15 amWinnipeg
6h 23m
1 stop
ORD3:38 pmChicago O'Hare Intl
Nov 22
ORD1:55 pmChicago O'Hare Intl
21h 05m
1 stop
YWG11:00 amWinnipeg
$467
Air Canada
Oct 23
YWG8:45 amWinnipeg
9h 45m
1 stop
ORD6:30 pmChicago O'Hare Intl
Nov 26
ORD4:30 pmChicago O'Hare Intl
8h 14m
1 stop
YWG12:44 amWinnipeg
$778
Air Canada
Oct 23
YWG2:00 pmWinnipeg
2h 35m
ORD4:35 pmChicago O'Hare Intl
Nov 26
ORD4:30 pmChicago O'Hare Intl
8h 14m
1 stop
YWG12:44 amWinnipeg
$818

Delta flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Delta deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Delta
Oct 17
YWG12:38 pmWinnipeg
8h 49m
1 stop
ORD9:27 pmChicago O'Hare Intl
Dec 25
ORD7:25 amChicago O'Hare Intl
17h 19m
2 stops
YWG12:44 amWinnipeg
$738
Delta
Oct 17
YWG6:40 amWinnipeg
5h 00m
1 stop
ORD11:40 amChicago O'Hare Intl
Dec 25
ORD6:23 amChicago O'Hare Intl
18h 21m
1 stop
YWG12:44 amWinnipeg
$753
Delta
Oct 17
YWG12:38 pmWinnipeg
8h 49m
1 stop
ORD9:27 pmChicago O'Hare Intl
Dec 22
ORD6:23 amChicago O'Hare Intl
6h 02m
1 stop
YWG12:25 pmWinnipeg
$825

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

Wed 12/16

7:00 am-6:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Sat 1/9

6:00 am-5:25 pm

2 stops35h 25m

$385

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/14

7:00 am-7:20 am

1 stop24h 20m

Chicago O'Hare Intl

Sat 1/9

6:00 am-5:25 pm

2 stops35h 25m

$385

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/16

7:00 am-6:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Wed 1/6

6:00 am-2:40 pm

1 stop8h 40m

$387

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/16

7:00 am-6:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Fri 1/8

6:00 am-2:40 pm

1 stop8h 40m

$400

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/19

9:15 am-3:38 pm

1 stop6h 23m

Chicago O'Hare Intl

Sun 11/22

1:55 pm-11:00 am

1 stop21h 05m

$467

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/27

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago O'Hare Intl

Wed 12/2

7:02 am-3:09 pm

1 stop8h 07m

$652
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 11/12

6:15 am-11:57 am

1 stop5h 42m

Chicago O'Hare Intl

Tue 11/17

9:35 am-1:23 pm

Nonstop3h 48m

$675

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/23

3:15 pm-5:02 pm

Nonstop1h 47m

Chicago O'Hare Intl

Tue 1/5

6:15 pm-3:09 pm

2 stops20h 54m

$729

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 2/1

4:05 pm-9:37 am

2 stops17h 32m

Chicago O'Hare Intl

Mon 2/8

6:15 pm-3:09 pm

2 stops20h 54m

$733

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 12/23

12:05 pm-7:55 am

2 stops19h 50m

Chicago O'Hare Intl

Tue 1/5

6:15 pm-3:09 pm

2 stops20h 54m

$738

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 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 $754 to $881.
The lowest price recently found on this route was $385.

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 $612. 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 $750.

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 $669 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $699. 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

$216

Fastest flight time

1h 31m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $216. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $385.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 1h 31m
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 1h 31m.

  • 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
7.4
10,366 reviews
Search United Airlines flights
Air CanadaPriceFrom $563Free CancellationRating
7.1
11,775 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 12 times per week, with 10,366 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 $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, 11,775 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with deals starting from $563 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

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