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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from $134

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 O'Hare Intl Airport departing on 5/2. 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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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to Chicago.
WestJet Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
WestJet Logo
5:30 pm - 5:41 pmORD-YWG
24h 11m1 stop
$211WestJet
Find Deal
mar., may. 27 - mié., may. 28
WestJet Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
WestJet Logo
1:40 pm - 9:26 pmORD-YWG
7h 46m1 stop
$264WestJet
Find Deal
lun., ago. 11 - sáb., ago. 16
 Logo
6:30 am - 4:44 pmYWG-ORD
10h 14m1 stop
 Logo
5:10 am - 4:28 pmORD-YWG
11h 18m1 stop
vie., may. 30 - lun., jun. 2
 Logo
6:20 pm - 4:44 pmYWG-ORD
22h 24m1 stop
 Logo
6:59 pm - 12:31 amORD-YWG
29h 32m2 stops
vie., may. 23 - dom., may. 25
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
7:10 am - 1:09 pmORD-YWG
5h 59m1 stop
$402United Airlines
Find Deal
vie., may. 23 - dom., may. 25
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:58 pm - 10:33 pmORD-YWG
2h 35mnonstop
$405United Airlines
Find Deal
vie., may. 23 - dom., may. 25
Air Canada Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
Air Canada Logo
7:58 pm - 10:33 pmORD-YWG
2h 35mnonstop
$406Air Canada
Find Deal
mar., may. 27 - mié., may. 28
Air Canada Logo
2:20 pm - 4:48 pmYWG-ORD
2h 28mnonstop
Air Canada Logo
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
$415Air Canada
Find Deal
sáb., abr. 26 - mié., may. 7
Delta Logo
6:40 am - 4:11 pmYWG-ORD
9h 31m2 stops
Delta Logo
11:03 am - 4:45 pmORD-YWG
5h 42m1 stop
$434Delta
Find Deal
sáb., abr. 26 - mié., may. 7
Delta Logo
5:43 pm - 8:41 amYWG-ORD
14h 58m2 stops
Delta Logo
6:35 am - 12:02 pmORD-YWG
5h 27m1 stop
$439Delta
Find Deal
jue., abr. 24 - lun., abr. 28

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
May 23
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
May 25
ORD7:10 amChicago O'Hare Intl
5h 59m
1 stop
YWG1:09 pmWinnipeg
United Airlines
May 23
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
May 25
ORD7:58 pmChicago O'Hare Intl
2h 35m
YWG10:33 pmWinnipeg
United Airlines
Jun 26
YWG5:00 amWinnipeg
7h 54m
1 stop
ORD12:54 pmChicago O'Hare Intl
Jul 6
ORD7:58 pmChicago O'Hare Intl
2h 35m
YWG10:33 pmWinnipeg

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
May 27
YWG8:30 amWinnipeg
8h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
May 28
ORD5:30 pmChicago O'Hare Intl
24h 11m
1 stop
YWG5:41 pmWinnipeg
WestJet
Aug 11
YWG8:30 amWinnipeg
8h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
Aug 16
ORD1:40 pmChicago O'Hare Intl
7h 46m
1 stop
YWG9:26 pmWinnipeg
WestJet
Aug 27
YWG8:30 amWinnipeg
8h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
Sep 2
ORD5:30 pmChicago O'Hare Intl
18h 11m
1 stop
YWG11:41 amWinnipeg

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 April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $464.

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 Wednesday when prices can be found for as low as $411. 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 $797.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $604 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $675. 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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Winnipeg when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $515 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Winnipeg for as low as $410 on momondo.

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.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

As of April 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 28% 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

$134

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 $134. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $211.
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.

  • 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
Air CanadaPriceFrom $244Free CancellationRating
7.0
9,028 reviews
Search Air Canada flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
8,616 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 8,616 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 $443 (round-trip), much lower than the average airfare cost of $547 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 (7.0/10, 9,028 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 7 times per week, with deals starting from $244 round-trip and rising to an average price of around $572.


Traveling to a place near Chicago?

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

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.


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