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Cheap flights from Winnipeg to Chicago from $171

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 5/4. 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

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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
$325WestJet
Fri, Sep 25 - Mon, Sep 28
Multiple Airlines Logo
7:30 am - 10:23 am
YWG
-
ORD
26h 53m
1 stop
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$345Multiple Airlines
Wed, Apr 22 - Thu, Apr 30
Multiple Airlines Logo
12:55 pm - 5:00 pm
YWG
-
ORD
28h 05m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$347Multiple Airlines
Wed, Apr 22 - Thu, Apr 30
Multiple Airlines Logo
9:20 am - 4:18 pm
YWG
-
ORD
6h 58m
1 stop
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$369Multiple Airlines
Tue, May 12 - Fri, May 15
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
$375WestJet
Fri, Sep 25 - Mon, Sep 28
Multiple Airlines Logo
6:15 am - 11:15 pm
YWG
-
ORD
17h 00m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$376Multiple Airlines
Mon, May 11 - Fri, May 15
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
1:18 pm - 12:55 am
ORD
-
YWG
35h 37m
2 stops
$380Multiple Airlines
Wed, Jun 3 - Wed, Jun 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
$401WestJet
Mon, May 11 - Fri, May 15
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
$404WestJet
Thu, Sep 17 - Sun, Sep 20
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
11:47 am - 10:10 pm
ORD
-
YWG
10h 23m
2 stops
$423Multiple Airlines
Fri, Sep 25 - Mon, Sep 28

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
May 12
YWG9:20 amWinnipeg
6h 58m
1 stop
ORD4:18 pmChicago O'Hare Intl
May 16
ORD8:06 amChicago O'Hare Intl
7h 13m
1 stop
YWG3:19 pmWinnipeg
$486
Porter Airlines
Apr 18
YWG6:00 amWinnipeg
6h 43m
1 stop
ORD12:43 pmChicago O'Hare Intl
Apr 26
ORD8:06 amChicago O'Hare Intl
7h 24m
1 stop
YWG3:30 pmWinnipeg
$591
Porter Airlines
Apr 8
YWG12:10 pmWinnipeg
7h 22m
1 stop
ORD7:32 pmChicago O'Hare Intl
Apr 15
ORD8:06 amChicago O'Hare Intl
7h 24m
1 stop
YWG3:30 pmWinnipeg
$765

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
Sep 25
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 28
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$325
WestJet
Sep 25
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 28
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$375
WestJet
May 11
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 15
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$401

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 April 4, 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-12:55 am

1 stop7h 25m

$325

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 4/22

7:30 am-10:23 am

1 stop26h 53m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-12:55 am

1 stop7h 25m

$345

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 4/22

12:55 pm-5:00 pm

2 stops28h 05m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-12:55 am

1 stop7h 25m

$347
Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 5/12

9:20 am-4:18 pm

1 stop6h 58m

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop7h 25m

$369

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-12:55 am

1 stop7h 25m

$375

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 5/11

6:15 am-11:15 pm

2 stops17h 00m

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop7h 25m

$376

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 6/3

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Wed 6/10

1:18 pm-12:55 am

2 stops35h 37m

$380

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 5/11

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop7h 25m

$401

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/17

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/20

5:30 pm-11:10 am

1 stop17h 40m

$404

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

11:47 am-10:10 pm

2 stops10h 23m

$423

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?

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

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $354.

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 Thursday when prices can be found for as low as $509. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $799.

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 $601 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $627. 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 flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl 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 15% 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

$218

Fastest flight time

2h 34m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $218. 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 34m
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 34m.

  • 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 $199Free CancellationRating
7.4
9,542 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 7 times per week, with 9,542 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 $199 (round-trip), much lower than the average airfare cost of $517 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
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
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

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