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YWG - ORD

Find cheap flights from Winnipeg to Chicago O'Hare Airport from $154

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 6/5. 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
Fri 6/7
Fri 6/14

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 43,968,530 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
6:55 am - 4:33 pmYWG-ORD
9h 38m2 stops
3:55 pm - 11:29 pmORD-YWG
7h 34m1 stop
$321Delta
Find Deal
Tue, Jun 4 - Tue, Jun 11
6:55 am - 7:32 amYWG-ORD
24h 37m2 stops
10:15 am - 11:29 pmORD-YWG
13h 14m2 stops
$330Delta
Find Deal
Mon, Jun 24 - Sat, Jun 29
8:00 am - 11:59 pmYWG-ORD
15h 59m1 stop
6:00 am - 11:21 pmORD-YWG
17h 21m1 stop
$340WestJet
Find Deal
Wed, Sep 18 - Tue, Sep 24
8:00 am - 11:59 pmYWG-ORD
15h 59m1 stop
6:00 am - 10:45 pmORD-YWG
16h 45m2 stops
$342WestJet
Find Deal
Wed, Sep 18 - Tue, Sep 24
8:00 am - 8:35 pmYWG-ORD
12h 35m1 stop
6:40 pm - 3:25 pmORD-YWG
20h 45m2 stops
Sun, May 26 - Tue, May 28
8:50 pm - 11:45 pmYWG-ORD
26h 55m3 stops
6:40 pm - 5:49 pmORD-YWG
47h 09m3 stops
Tue, Jun 4 - Tue, Jun 11
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
4:00 pm - 12:07 amORD-YWG
8h 07m1 stop
$457Air Canada
Find Deal
Mon, Jun 24 - Sat, Jun 29
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
9:15 pm - 8:55 amORD-YWG
11h 40m1 stop
$463Air Canada
Find Deal
Tue, Jun 4 - Sat, Jun 8
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
5:00 pm - 12:10 amORD-YWG
7h 10m1 stop
$496United Airlines
Find Deal
Sat, Jun 8 - Tue, Jun 11
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
11:00 am - 5:55 pmORD-YWG
6h 55m1 stop
$503United Airlines
Find Deal
Wed, May 29 - Sun, Jun 2

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 Wednesday 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 November, 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 $601 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 $321 on Delta, followed by WestJet ($340). One-way flight deals have also been found from as low as $226 on Delta and from $274 on WestJet.

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 21m.

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 2:18 pm and lands at 4:46 pm.

Good to know

Low season

July

High season

May

Cheapest flight

$154
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 29% 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 $154 for a one-way ticket and $321 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 $554 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

Top tips for finding a cheap flight from YWG to Chicago O'Hare Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $571 or less one-way and $496 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 10789 reviews
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

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.
6/5Wed
1 stop
12h 47mYWG-ORD
$154
6/5Wed
2 stops
15h 45mYWG-ORD
$174
6/5Wed
3 stops
22h 36mYWG-ORD
$195
7/8Mon
1 stop
8h 31mYWG-ORD
$208
7/14Sun
1 stopDelta
8h 12mYWG-ORD
$226
7/14Sun
2 stopsWestJet
24h 51mYWG-ORD
$274
7/14Sun
2 stopsWestJet
27h 09mYWG-ORD
$275
6/5Wed
nonstopUnited Airlines
2h 28mYWG-ORD
$409
7/8Mon
nonstopAir Canada
2h 28mYWG-ORD
$573
7/14Sun
nonstopUnited Airlines
2h 28mYWG-ORD
$711

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Winnipeg - Chicago O'Hare Airport Flights

Departure:

Winnipeg (undefined)Canada

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Winnipeg

Cabin classes:

$531
$2,001
$238