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YWG - ORD

$139 Find cheap flights from Winnipeg to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to O'Hare Intl departing on 7/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,212,782 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Winnipeg to O'Hare Intl (YWG-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:00 am - 8:58 pmYWG-ORD
12h 58m1 stop
5:55 pm - 9:23 pmORD-YWG
27h 28m1 stop
Thu, Jul 11 - Sun, Jul 14
8:00 am - 11:17 pmYWG-ORD
15h 17m1 stop
9:40 pm - 7:57 pmORD-YWG
22h 17m2 stops
Fri, Aug 23 - Mon, Aug 26
6:55 am - 8:57 pmYWG-ORD
14h 02m2 stops
7:05 am - 11:28 pmORD-YWG
16h 23m2 stops
$351Delta
Find Deal
Wed, Jul 10 - Wed, Jul 17
5:20 pm - 4:57 pmYWG-ORD
23h 37m2 stops
5:55 pm - 11:13 pmORD-YWG
29h 18m1 stop
$375WestJet
Find Deal
Thu, Jul 11 - Sun, Jul 14
8:30 am - 4:57 pmYWG-ORD
8h 27m1 stop
5:55 pm - 11:38 amORD-YWG
17h 43m1 stop
$387WestJet
Find Deal
Wed, Jul 10 - Wed, Jul 17
8:00 am - 8:13 amYWG-ORD
24h 13m1 stop
7:05 am - 3:22 pmORD-YWG
8h 17m1 stop
$419Delta
Find Deal
Fri, Aug 23 - Mon, Aug 26
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
1:15 pm - 3:41 pmORD-YWG
2h 26mnonstop
$458Air Canada
Find Deal
Wed, Jul 10 - Sun, Jul 14
8:15 am - 2:40 pmYWG-ORD
6h 25m1 stop
1:15 pm - 3:41 pmORD-YWG
2h 26mnonstop
$460Air Canada
Find Deal
Wed, Jul 10 - Wed, Jul 17
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
5:12 am - 1:21 pmORD-YWG
8h 09m1 stop
$464United Airlines
Find Deal
Wed, Jul 10 - Sun, Jul 14
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
5:12 am - 1:21 pmORD-YWG
8h 09m1 stop
$465United Airlines
Find Deal
Wed, Jul 10 - Sun, Jul 14

Flights from Winnipeg to O'Hare Intl - Travel Insights & Trends

Get data-powered insights and trends into flights from Winnipeg to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Winnipeg to Chicago O'Hare Airport?

The average price of all flights from Winnipeg to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
When flying from Winnipeg to Chicago O'Hare Airport, you should consider leaving on a Monday and avoid Tuesdays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Winnipeg to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Winnipeg to Chicago O'Hare Intl Airport is July, where tickets cost $423 on average. On the other hand, the most expensive months are May and August, where the average cost of tickets is $694 and $602 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Winnipeg to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Winnipeg to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 41 days before departure.

Which airlines provide the cheapest flights from Winnipeg to Chicago O'Hare Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Winnipeg to Chicago O'Hare Airport found by KAYAK users in the last 72 hours was for $351 on Delta, followed by WestJet ($375). One-way flight deals have also been found from as low as $139 on WestJet and from $171 on Delta.

How many flights are there between Winnipeg and Chicago O'Hare Intl Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Winnipeg and lands in Chicago O'Hare Intl Airport, with an average flight time of 2h 28m. The most common departure time is 2:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

Which cabin class options are there for flights between Winnipeg and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are First and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Winnipeg to Chicago O'Hare Airport take?

Direct flights cover the 706 miles separating Winnipeg to Chicago O'Hare Airport in about 2h 28m.

What’s the earliest departure time from Winnipeg to Chicago O'Hare Airport?

Early birds can take the earliest flight from Winnipeg at 2:18 pm and will be landing in Chicago O'Hare Intl Airport at 4:46 pm.

What’s the latest departure time from Winnipeg to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Winnipeg to Chicago O'Hare Intl Airport jets off at 2:25 pm and lands at 4:53 pm.

Good to know

Low season

January

High season

May

Cheapest flight

$139
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Winnipeg to Chicago O'Hare Airport

When to book flights from Winnipeg to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Winnipeg to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Winnipeg to Chicago O'Hare Airport flights

  • What is the cheapest flight from Winnipeg to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Winnipeg to Chicago O'Hare Intl Airport was $139 for a one-way ticket and $328 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Chicago O'Hare Airport?

    Yes

  • Which airports will I be using when flying from Winnipeg to Chicago O'Hare Airport?

    Winnipeg airport is called Winnipeg and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Winnipeg to Chicago O'Hare Airport?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Winnipeg to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Winnipeg to Chicago O'Hare Airport?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Chicago O'Hare Airport.

  • On which days can I fly direct from Winnipeg to Chicago O'Hare Airport?

    There are nonstop flights from Winnipeg to Chicago O'Hare Airport on a daily basis.

  • Which is the best airline for flights from Winnipeg to Chicago, Delta or Air Canada?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Chicago are Delta and Air Canada. With an average price for the route of $545 and an overall rating of 8.0, Delta is the most popular choice. Air Canada is also a great choice for the route, with an average price of $470 and an overall rating of 7.0.

  • How does KAYAK find such low prices on flights from Winnipeg to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back to Winnipeg with another airline. Booking your flights between Winnipeg and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Winnipeg to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $253 or less one-way and $533 or less round-trip.

Prefer to fly non-stop from Winnipeg to Chicago O'Hare Airport?

Find which airlines fly direct from Winnipeg to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Tuesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Wednesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Thursday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Friday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Saturday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Sunday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Tuesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Wednesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Thursday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Friday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Saturday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Sunday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

See more direct flights
See more direct flights

Top airlines flying from Winnipeg to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10277 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Ongoing flight was delayed. Staff at bag recheck was able to get us on an earlier flight. With only 20 minutes till take off we feared our bags would not make the new earlier flight. We were most delighted that they did and were there when we landed. Delta came through

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

The flight was very turbulent. The who 3 hours we mostly needed seat belts. Plane is older and does not have tv screens so no entertainment.

Experienced flight cancelations and delays in 5 days. They seem pretty common to AC. Experienced with one of AC's check-in agents at the counter of a big liar. She lied and acted (yes like acting in a movie) that an early flight was fully booked and refused to rebook me, but my flight was delayed two hours so I could not make my connection. Later, I got help at the gate to switch the early flight (Big thanks to that agent). Ater boading, I found the early flight was only 2/3 full meaning there was almost one vacant seat in a 3-person seater, and multiple empty 3-seaters. AC is wired that it is filled with good and bad employees. BTW, AC employees seem never smile, or they don't know how.

Not much food/snacks. I had just tea and it was so bitter.

My husbands flight last night Vancouver/Sydney was 90 minutes late in leaving. My flight tonight Vancouver/Seattle was also late in departing.

My mother, 80years old, had arranged for wheelchair assist to and from the aircraft cabin and in the airport but, no one showed up for her to de-plane. Apart from Air Canada having a reputation of being late for every leg of its flight so nothing was new this time so this time they did worse by not assisting seniors. I guess our whole family is done with this airline

Flights delayed over 4 hours with no compensation. No agents at counters to assist with re-booking.

Seating for almost 3 hours in the plan before aircraft takeoff. Very exhausted .

The bathroom did not have hand soap. That is unacceptable.

The only problem I encountered was they changed the gate on me while I was sitting down but no one notified me, they had sent me an email and by coincidence I checked it and found out that they had changed my boarding terminal. No one notified me and when I had asked the lady she told me yes this is the spot while they had already changed to another gate/terminal

I was seated next to someone who was, to be polite, not a small person. I had to press myself against the wall as I had no personal space. Aside from that the crew was wonderful and they got me home safely, which is the most important part of my journey. I am very appreciative to your air crews for the job they have, which isn't easy, and appreciative of the fact that they are professional and courteous. The employees I encountered on my journey, with the few exceptions I mentioned in a previous review, are a credit to Air Canada.

Book cheap flights from Winnipeg to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Winnipeg to Chicago found on KAYAK in the last 72 hours.
7/20Sat
1 stopWestJet
8h 27mYWG-ORD
$139
8/18Sun
1 stopWestJet
22h 42mYWG-ORD
$165
8/20Tue
2 stopsDelta
11h 35mYWG-ORD
$171
7/13Sat
2 stops
14h 09mYWG-ORD
$195
7/10Wed
3 stops
23h 19mYWG-ORD
$196
8/18Sun
3 stops
27h 05mYWG-ORD
$205
7/14Sun
nonstopUnited Airlines
2h 28mYWG-ORD
$257
7/14Sun
2 stopsDelta
5h 46mYWG-ORD
$327
8/18Sun
nonstopUnited Airlines
2h 28mYWG-ORD
$530
6/16Sun
nonstopAir Canada
2h 28mYWG-ORD
$661

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Winnipeg - Chicago O'Hare Airport Flights

Departure:

Winnipeg (YWG)Canada

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Winnipeg

Cabin classes:

$1,308
$531
$2,001
$405