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Cheap flights from Winnipeg to Chicago from $123

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 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m1 stop
$195WestJet
Fri, Feb 20 - Fri, Feb 27
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
1:40 pm - 11:10 pm
ORD
-
YWG
9h 30m1 stop
$208WestJet
Wed, Jun 24 - Sat, Jul 11
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 2:30 pm
ORD
-
YWG
21h 00m1 stop
$221WestJet
Wed, May 20 - Sun, May 24
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m1 stop
$227WestJet
Thu, May 14 - Sun, May 17
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m1 stop
$233WestJet
Thu, Jun 11 - Thu, Jun 18
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 8:27 am
ORD
-
YWG
18h 07m2 stops
$240WestJet
Mon, Feb 2 - Mon, Feb 9
Multiple Airlines Logo
9:00 pm - 6:27 pm
YWG
-
ORD
21h 27m2 stops
Multiple Airlines Logo
6:07 pm - 3:09 pm
ORD
-
YWG
21h 02m1 stop
$242Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:33 am
ORD
-
YWG
18h 03m2 stops
$245WestJet
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
Multiple Airlines Logo
7:00 am - 12:41 am
ORD
-
YWG
17h 41m2 stops
$257Multiple Airlines
Fri, Mar 6 - Wed, Mar 11
Multiple Airlines Logo
9:00 pm - 1:37 pm
YWG
-
ORD
16h 37m2 stops
Multiple Airlines Logo
2:53 pm - 3:09 pm
ORD
-
YWG
24h 16m1 stop
$263Multiple Airlines
Sat, Jan 31 - Tue, Feb 3

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
Feb 20
YWG6:15 amWinnipeg
7h 20m
1 stop
ORD1:35 pmChicago O'Hare Intl
Feb 27
ORD2:20 pmChicago O'Hare Intl
8h 20m
1 stop
YWG10:40 pmWinnipeg
$195
Find similar
WestJet
Jun 24
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Jul 11
ORD1:40 pmChicago O'Hare Intl
9h 30m
1 stop
YWG11:10 pmWinnipeg
$208
Find similar
WestJet
May 20
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
May 24
ORD5:30 pmChicago O'Hare Intl
21h 00m
1 stop
YWG2:30 pmWinnipeg
$221
Find similar

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
Jan 8
YWG5:30 amWinnipeg
7h 31m
1 stop
ORD1:01 pmChicago O'Hare Intl
Jan 10
ORD9:10 amChicago O'Hare Intl
2h 47m
YWG11:57 amWinnipeg
$943
Find similar
United Airlines
Jan 8
YWG1:30 pmWinnipeg
6h 15m
1 stop
ORD7:45 pmChicago O'Hare Intl
Jan 10
ORD2:00 pmChicago O'Hare Intl
5h 34m
1 stop
YWG7:34 pmWinnipeg
$952
Find similar

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 January 7, 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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 2/20

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Fri 2/27

2:20 pm-10:40 pm

1 stop8h 20m

$195

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 6/24

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sat 7/11

1:40 pm-11:10 pm

1 stop9h 30m

$208

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 5/20

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/24

5:30 pm-2:30 pm

1 stop21h 00m

$221

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/14

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/17

5:30 pm-11:40 am

1 stop18h 10m

$227

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 6/11

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Thu 6/18

5:30 pm-11:40 am

1 stop18h 10m

$233

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 2/2

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-8:27 am

2 stops18h 07m

$240

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 2/3

9:00 pm-6:27 pm

2 stops21h 27m

Chicago O'Hare Intl

Tue 2/10

6:07 pm-3:09 pm

1 stop21h 02m

$242

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/14

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 5/17

5:30 pm-11:33 am

2 stops18h 03m

$245

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 3/6

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 3/11

7:00 am-12:41 am

2 stops17h 41m

$257

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 1/31

9:00 pm-1:37 pm

2 stops16h 37m

Chicago O'Hare Intl

Tue 2/3

2:53 pm-3:09 pm

1 stop24h 16m

$263

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 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 $370.

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 $533. 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 $836.

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 $606 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $617. 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 42% 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?

As of January 2026, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 81% more expensive when compared to flights at the same time last year.

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

$428

Fastest flight time

2h 21m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $428. 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 2h 21m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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 $199Free CancellationRating
7.4
9,138 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 9,138 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 $471 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
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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