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Cheap flights from Winnipeg to Chicago from $172

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 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$294WestJet
Mon, Oct 19 - Thu, Oct 22
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$297WestJet
Mon, Oct 19 - Thu, Oct 22
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 9:35 amORD  Chicago O'Hare Intl-YWG Winnipeg
16h 05m2 stops Calgary Saskatoon
$334WestJet
Mon, Oct 19 - Thu, Oct 22
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 9:35 amORD  Chicago O'Hare Intl-YWG Winnipeg
16h 05m2 stops Calgary Saskatoon
$352WestJet
Mon, Oct 19 - Thu, Oct 22
WestJet Logo
7:10 pm - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
21h 30m1 stop Calgary
WestJet Logo
5:30 pm - 11:10 amORD  Chicago O'Hare Intl-YWG Winnipeg
17h 40m1 stop Calgary
$366WestJet
Wed, Oct 14 - Mon, Oct 19
Multiple Airlines Logo
5:00 am - 5:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
12h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$368Multiple Airlines
Tue, Oct 27 - Wed, Oct 28
Multiple Airlines Logo
5:00 am - 5:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
12h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$371Multiple Airlines
Tue, Nov 24 - Sun, Nov 29
Multiple Airlines Logo
11:40 am - 5:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
30h 00m2 stops Ottawa Toronto Island
Multiple Airlines Logo
6:20 pm - 9:15 amORD  Chicago O'Hare Intl-YWG Winnipeg
14h 55m1 stop Toronto Island
$382Multiple Airlines
Tue, Nov 24 - Sun, Nov 29
United Airlines Logo
11:05 am - 9:15 amYWG  Winnipeg-ORD Chicago O'Hare Intl
22h 10m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
United Airlines Logo
6:20 pm - 11:49 amORD  Chicago O'Hare Intl-YWG Winnipeg
17h 29m2 stops Boston Logan Intl Toronto Pearson Intl
$662United Airlines
Mon, Dec 7 - Tue, Dec 8
United Airlines Logo
2:15 pm - 4:50 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 35mnonstop
United Airlines Logo
9:29 am - 12:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 54mnonstop
$679United Airlines
Tue, Oct 27 - Wed, Oct 28

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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 19
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 22
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$294
WestJet
Oct 19
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 22
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$297
WestJet
Oct 19
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 22
ORD5:30 pmChicago O'Hare Intl
16h 05m
2 stops
YWG9:35 amWinnipeg
$334

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
Sep 28
YWG5:25 pmWinnipeg
19h 58m
1 stop
ORD1:23 pmChicago O'Hare Intl
Sep 30
ORD10:43 amChicago O'Hare Intl
7h 29m
1 stop
YWG6:12 pmWinnipeg
$657
Air Canada
Sep 28
YWG5:25 pmWinnipeg
19h 58m
1 stop
ORD1:23 pmChicago O'Hare Intl
Sep 30
ORD10:43 amChicago O'Hare Intl
7h 29m
1 stop
YWG6:12 pmWinnipeg
$701
Air Canada
Sep 28
YWG2:00 pmWinnipeg
2h 35m
ORD4:35 pmChicago O'Hare Intl
Sep 30
ORD10:43 amChicago O'Hare Intl
7h 29m
1 stop
YWG6:12 pmWinnipeg
$746

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.

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Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

$294

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-12:55 am

1 stop7h 25m

$297

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-9:35 am

2 stops16h 05m

$334

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 10/19

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 10/22

5:30 pm-9:35 am

2 stops16h 05m

$352

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 10/14

7:10 pm-4:40 pm

1 stop21h 30m

Chicago O'Hare Intl

Mon 10/19

5:30 pm-11:10 am

1 stop17h 40m

$366

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 10/27

5:00 am-5:40 pm

1 stop12h 40m

Chicago O'Hare Intl

Wed 10/28

6:20 pm-9:15 am

1 stop14h 55m

$368

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 11/24

5:00 am-5:40 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 11/29

6:20 pm-9:15 am

1 stop14h 55m

$371

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 11/24

11:40 am-5:40 pm

2 stops30h 00m

Chicago O'Hare Intl

Sun 11/29

6:20 pm-9:15 am

1 stop14h 55m

$382

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 12/7

11:05 am-9:15 am

2 stops22h 10m

Chicago O'Hare Intl

Tue 12/8

6:20 pm-11:49 am

2 stops17h 29m

$662
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 10/27

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago O'Hare Intl

Wed 10/28

9:29 am-12:23 pm

Nonstop2h 54m

$679

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 $388 to $754.
The lowest price recently found on this route was $294.

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 $602. 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 $793.

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 at noon because they tend to be around $680. 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 57% 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

$172

Fastest flight time

2h 31m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $172. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $294.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 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 2h 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 $471Free CancellationRating
7.4
10,232 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 10 times per week, with 10,232 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 $471 (round-trip), much lower than the average airfare cost of $701 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
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

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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