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Cheap flights from Winnipeg to Chicago O'Hare Intl Airport from $138

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 1/19. 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

These are some of the best round-trip flight deals from Winnipeg to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Winnipeg to Chicago.

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Planning a quick getaway from Winnipeg to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Winnipeg to Chicago

Find recent round-trip train or bus tickets from Winnipeg to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:30 am - 5:55 amYWG-ORD
22h 25m2 stops
3:56 pm - 11:20 pmORD-YWG
31h 24m3 stops
Tue, Jan 21 - Tue, Jan 28
7:00 pm - 8:13 pmYWG-ORD
25h 13m2 stops
5:11 am - 10:45 amORD-YWG
29h 34m2 stops
Tue, Jan 21 - Tue, Jan 28
5:37 pm - 9:58 pmYWG-ORD
4h 21m1 stop
6:35 pm - 11:55 amORD-YWG
17h 20m2 stops
$416Delta
Find Deal
Fri, Jan 17 - Fri, Jan 24
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$421Air Canada
Find Deal
Wed, Jan 29 - Wed, Feb 5
2:20 pm - 4:48 pmYWG-ORD
2h 28mnonstop
9:15 pm - 1:09 pmORD-YWG
15h 54m1 stop
$426United Airlines
Find Deal
Fri, Apr 4 - Mon, Apr 7
12:45 pm - 5:29 pmYWG-ORD
4h 44m1 stop
6:45 am - 4:47 pmORD-YWG
10h 02m2 stops
$431Delta
Find Deal
Tue, Jan 21 - Tue, Jan 28
4:25 pm - 12:35 amYWG-ORD
8h 10m1 stop
7:50 pm - 1:09 pmORD-YWG
17h 19m1 stop
$432United Airlines
Find Deal
Fri, Apr 4 - Mon, Apr 7
12:20 pm - 8:34 pmYWG-ORD
8h 14m2 stops
4:45 pm - 9:08 amORD-YWG
16h 23m1 stop
$436WestJet
Find Deal
Fri, Apr 4 - Mon, Apr 7
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
7:10 am - 1:27 pmORD-YWG
6h 17m1 stop
$448Air Canada
Find Deal
Fri, Jan 17 - Sun, Jan 19
12:20 pm - 8:34 pmYWG-ORD
8h 14m2 stops
4:45 pm - 12:08 pmORD-YWG
19h 23m1 stop
$460WestJet
Find Deal
Fri, Apr 4 - Mon, Apr 7
7:30 am - 10:27 pmYWG-ORD
14h 57m1 stop
Sun, Jan 19
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
$171WestJet
Find Deal
Sat, May 31
4:25 pm - 6:07 amYWG-ORD
13h 42m2 stops
Tue, Feb 11
7:30 am - 5:55 amYWG-ORD
22h 25m2 stops
Wed, Jan 15
7:15 am - 2:45 pmYWG-ORD
7h 30m1 stop
$237Air Canada
Find Deal
Tue, Feb 11
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$258United Airlines
Find Deal
Wed, Jan 15
5:37 pm - 9:58 pmYWG-ORD
4h 21m1 stop
$264Delta
Find Deal
Wed, Jan 15
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$286United Airlines
Find Deal
Thu, Jan 9
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$287Air Canada
Find Deal
Thu, Jan 9
5:37 pm - 9:58 pmYWG-ORD
4h 21m1 stop
$293Delta
Find Deal
Thu, Jan 9
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
8:30 pm - 8:28 amORD-YWG
11h 58m1 stop
$725Air Canada
Find Deal
Tue, Dec 24 - Sat, Jan 4
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$751Air Canada
Find Deal
Tue, Dec 24 - Tue, Dec 31
6:00 am - 10:52 pmYWG-ORD
16h 52m2 stops
5:50 pm - 11:52 amORD-YWG
18h 02m1 stop
$753WestJet
Find Deal
Wed, Dec 25 - Sat, Jan 4
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
2:05 pm - 8:58 pmORD-YWG
6h 53m1 stop
$757Air Canada
Find Deal
Tue, Dec 24 - Tue, Dec 31
5:00 am - 4:40 pmYWG-ORD
11h 40m2 stops
5:50 pm - 11:52 amORD-YWG
18h 02m1 stop
$759WestJet
Find Deal
Thu, Dec 26 - Sat, Jan 4
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
8:45 am - 9:10 pmORD-YWG
12h 25m1 stop
$788Air Canada
Find Deal
Tue, Dec 24 - Thu, Jan 2
6:00 am - 10:52 pmYWG-ORD
16h 52m2 stops
5:50 pm - 11:52 amORD-YWG
18h 02m1 stop
$841WestJet
Find Deal
Tue, Dec 24 - Sat, Jan 4
6:55 am - 6:52 pmYWG-ORD
11h 57m2 stops
7:05 am - 3:10 pmORD-YWG
8h 05m1 stop
$950Delta
Find Deal
Tue, Dec 24 - Wed, Jan 1
5:00 am - 4:40 pmYWG-ORD
11h 40m2 stops
6:20 am - 11:52 amORD-YWG
5h 32m1 stop
$956Delta
Find Deal
Thu, Dec 26 - Fri, Jan 3
12:42 pm - 11:56 pmYWG-ORD
11h 14m2 stops
10:05 am - 4:54 pmORD-YWG
6h 49m1 stop
$987Delta
Find Deal
Tue, Dec 24 - Fri, Jan 3
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:58 pm - 3:28 pmORD-YWG
2h 30mnonstop
$414United Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 25
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$416Air Canada
Find Deal
Wed, Jan 29 - Wed, Feb 5
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$437United Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$439United Airlines
Find Deal
Fri, Jan 17 - Fri, Jan 24
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$447United Airlines
Find Deal
Fri, Jan 17 - Fri, Jan 24
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$526United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
2:20 pm - 4:48 pmYWG-ORD
2h 28mnonstop
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
$542United Airlines
Find Deal
Fri, Apr 4 - Mon, Apr 7
2:20 pm - 4:48 pmYWG-ORD
2h 28mnonstop
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
$543United Airlines
Find Deal
Fri, Apr 4 - Mon, Apr 7
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$564Air Canada
Find Deal
Fri, Jan 10 - Sun, Jan 12
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$565Air Canada
Find Deal
Fri, Jan 10 - Sun, Jan 12

Delta flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Delta deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Delta
Jan 17
YWG5:37 pmWinnipeg
4h 21m
1 stop
ORD9:58 pmChicago O'Hare Intl
Jan 24
ORD6:35 pmChicago O'Hare Intl
17h 20m
2 stops
YWG11:55 amWinnipeg
Delta
Jan 21
YWG12:45 pmWinnipeg
4h 44m
1 stop
ORD5:29 pmChicago O'Hare Intl
Jan 28
ORD6:45 amChicago O'Hare Intl
10h 02m
2 stops
YWG4:47 pmWinnipeg
Delta
Jan 18
YWG12:45 pmWinnipeg
4h 44m
1 stop
ORD5:29 pmChicago O'Hare Intl
Sep 3
ORD8:55 amChicago O'Hare Intl
11h 13m
2 stops
YWG8:08 pmWinnipeg

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
Apr 4
YWG2:20 pmWinnipeg
2h 28m
ORD4:48 pmChicago O'Hare Intl
Apr 7
ORD9:15 pmChicago O'Hare Intl
15h 54m
1 stop
YWG1:09 pmWinnipeg
United Airlines
Apr 4
YWG4:25 pmWinnipeg
8h 10m
1 stop
ORD12:35 amChicago O'Hare Intl
Apr 7
ORD7:50 pmChicago O'Hare Intl
17h 19m
1 stop
YWG1:09 pmWinnipeg
United Airlines
Jan 18
YWG2:15 pmWinnipeg
2h 36m
ORD4:51 pmChicago O'Hare Intl
Jan 25
ORD12:56 pmChicago O'Hare Intl
2h 32m
YWG3:28 pmWinnipeg

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 March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $443.

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 $471. 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 $671.

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 $470 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $533. 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?

In general, most travelers find the cheapest time to book a flight to Chicago O'Hare Intl Airport is about 43 days prior to their departure date when tickets on average are $517. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $261.

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 24% 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 December 2024, prices for Winnipeg to Chicago O'Hare Intl Airport flights are approximately 14% 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

$138

Fastest flight time

2h 28m

Direct flights

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 $138. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $349.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 28m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport on Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.

  • 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 28m.

  • 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 $289Free CancellationRating
7.0
8,403 reviews
Search Air Canada flights
DeltaPriceFrom $370Free CancellationRating
8.0
8,597 reviews
Search Delta flights
United AirlinesPriceFrom $441Free CancellationRating
7.4
9,039 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 9,039 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 $441 (round-trip), much lower than the average airfare cost of $533 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, 8,403 ratings). Air Canada flies from Winnipeg to Chicago O'Hare Intl Airport around 7 times per week, with deals starting from $289 round-trip and rising to an average price of around $550.


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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