Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from $117

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 9/29. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:41 amORD-YWG
18h 11m1 stop
$207WestJet
Find Deal
Mon, Sep 29 - Mon, Oct 6
Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
Logo
1:26 pm - 3:55 pmORD-YWG
26h 29m1 stop
$218
Find Deal
Sun, Oct 19 - Thu, Oct 23
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:41 amORD-YWG
18h 11m1 stop
$226WestJet
Find Deal
Mon, Sep 22 - Fri, Sep 26
Logo
6:30 am - 4:43 pmYWG-ORD
10h 13m1 stop
Logo
1:26 pm - 3:55 pmORD-YWG
26h 29m1 stop
$232
Find Deal
Sat, Oct 18 - Thu, Oct 23
Logo
9:10 am - 9:58 pmYWG-ORD
12h 48m1 stop
Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$239
Find Deal
Sat, Sep 13 - Sat, Sep 20
Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
Logo
1:26 pm - 12:13 amORD-YWG
10h 47m2 stops
$240
Find Deal
Sun, Oct 19 - Thu, Oct 23
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$334United Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
$336United Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
$343United Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:15 am - 1:09 pmORD-YWG
5h 54m1 stop
$344United Airlines
Find Deal
Wed, Sep 10 - Sat, Sep 13

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 29
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 6
ORD5:30 pmChicago O'Hare Intl
18h 11m
1 stop
YWG11:41 amWinnipeg
$207
Find similar
WestJet
Sep 22
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 26
ORD5:30 pmChicago O'Hare Intl
18h 11m
1 stop
YWG11:41 amWinnipeg
$226
Find similar
WestJet
Sep 28
YWG5:30 pmWinnipeg
23h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 5
ORD5:30 pmChicago O'Hare Intl
26h 45m
1 stop
YWG8:15 pmWinnipeg
$242
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
Sep 18
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Sep 21
ORD1:01 pmChicago O'Hare Intl
2h 30m
YWG3:31 pmWinnipeg
$334
Find similar
United Airlines
Sep 18
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Sep 21
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
$336
Find similar
United Airlines
Sep 4
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Sep 7
ORD7:54 pmChicago O'Hare Intl
2h 39m
YWG10:33 pmWinnipeg
$343
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 August 15, 2025.
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

Mon 9/29

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 10/6

5:30 pm-11:41 am

1 stop18h 11m

$207

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/19

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Thu 10/23

1:26 pm-3:55 pm

1 stop26h 29m

$218

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/22

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Fri 9/26

5:30 pm-11:41 am

1 stop18h 11m

$226

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/18

6:30 am-4:43 pm

1 stop10h 13m

Chicago O'Hare Intl

Thu 10/23

1:26 pm-3:55 pm

1 stop26h 29m

$232

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/13

9:10 am-9:58 pm

1 stop12h 48m

Chicago O'Hare Intl

Sat 9/20

1:40 pm-9:25 pm

1 stop7h 45m

$239

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 10/19

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Thu 10/23

1:26 pm-12:13 am

2 stops10h 47m

$240

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/18

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

1:01 pm-3:31 pm

Nonstop2h 30m

$334

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/18

2:20 pm-4:51 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

7:54 pm-10:33 pm

Nonstop2h 39m

$336

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/4

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/7

7:54 pm-10:33 pm

Nonstop2h 39m

$343

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/10

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

Sat 9/13

7:15 am-1:09 pm

1 stop5h 54m

$344

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $389.

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 Friday when prices can be found for as low as $524. 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 $562 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $628. 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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $448 when searching 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 $244 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.

Can stopping save me money on Winnipeg to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Winnipeg to Chicago O'Hare Intl Airport.

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

As of August 2025, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 24% 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

$117

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 $117. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $207.
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

  • 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 $199Free CancellationRating
7.4
8,915 reviews
Search United Airlines flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
9,956 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 8,915 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 $487 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, 9,956 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 14 times per week, with deals starting from $230 round-trip and rising to an average price of around $645.

Traveling to a place near Chicago?

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

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 8/20
Wed 8/27
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago