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ORD - YWG

Find cheap flights from Chicago O'Hare Airport to Winnipeg from $195

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Winnipeg departing on 7/21. 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 5/24
Fri 5/31

Search hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, 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 Chicago to Winnipeg, as well as popular online travel agencies
In the last 7 days travelers have searched 44,979,812 times on KAYAK, and here is why:

Save 22% 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 O'Hare Intl to Winnipeg (ORD-YWG)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Winnipeg 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
5:56 pm - 12:44 amORD-YWG
30h 48m2 stops
8:30 am - 5:05 pmYWG-ORD
8h 35m1 stop
Thu, May 23 - Thu, May 30
5:40 am - 3:25 pmORD-YWG
9h 45m1 stop
8:30 am - 5:05 pmYWG-ORD
8h 35m1 stop
$392WestJet
Find Deal
Wed, May 29 - Fri, May 31
3:55 pm - 11:29 pmORD-YWG
7h 34m1 stop
6:55 am - 2:59 pmYWG-ORD
8h 04m1 stop
$398Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
1:13 pm - 12:44 amORD-YWG
11h 31m1 stop
8:00 am - 4:28 pmYWG-ORD
8h 28m1 stop
Thu, May 23 - Thu, May 30
3:55 pm - 11:29 pmORD-YWG
7h 34m1 stop
6:55 am - 4:48 pmYWG-ORD
9h 53m2 stops
$415Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
7:00 am - 3:25 pmORD-YWG
8h 25m1 stop
8:00 am - 6:34 pmYWG-ORD
10h 34m1 stop
Wed, May 29 - Thu, Jul 4
9:15 pm - 9:47 amORD-YWG
12h 32m1 stop
7:30 am - 2:54 pmYWG-ORD
7h 24m1 stop
$444Air Canada
Find Deal
Fri, Jun 21 - Tue, Jun 25
11:00 am - 5:55 pmORD-YWG
6h 55m1 stop
5:10 am - 1:00 pmYWG-ORD
7h 50m1 stop
$481Air Canada
Find Deal
Sat, May 18 - Sun, May 19
1:03 pm - 3:29 pmORD-YWG
2h 26mnonstop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$716United Airlines
Find Deal
Thu, May 23 - Thu, Jul 4
1:03 pm - 3:29 pmORD-YWG
2h 26mnonstop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$775United Airlines
Find Deal
Thu, May 23 - Tue, Jul 9

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

Get data-powered insights and trends into flights from O'Hare Intl to Winnipeg 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 Chicago O'Hare Airport to Winnipeg?

The average price of all flights from Chicago O'Hare Intl Airport to Winnipeg clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago O'Hare Airport to Winnipeg, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Winnipeg, Wednesday is the cheapest day to fly and Tuesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Winnipeg, 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 Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost $381 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is $897 and $737 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Winnipeg, 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 Chicago O'Hare Intl Airport to Winnipeg, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago O'Hare Airport to Winnipeg were found on WestJet ($392) and Delta ($398). Delta proposed the cheapest one-way flight at $219.

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Winnipeg?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago O'Hare Intl Airport to Winnipeg.
There is just one airline that flies from Chicago O'Hare Intl Airport to Winnipeg direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $574.

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

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Winnipeg, with an average flight time of 2h 26m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

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

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is 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 Chicago O'Hare Airport to Winnipeg take?

A direct flight to Winnipeg will take on average 2h 26m to travel the 706 miles flying distance from Chicago O'Hare Airport.

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

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 1:03 pm and will be landing in Winnipeg at 3:29 pm.

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

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 1:03 pm and lands at 3:29 pm.

Good to know

Low season

January

High season

July

Cheapest flight

$195
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago O'Hare Airport to Winnipeg

When to book flights from O'Hare Intl to Winnipeg

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Winnipeg 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 Chicago O'Hare Airport to Winnipeg flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was $195 for a one-way ticket and $378 for a round-trip.

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

    A passport is required to fly from Chicago O'Hare Airport to Winnipeg.

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

    On your way to Winnipeg, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Winnipeg.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to Winnipeg flight route.

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Winnipeg are Delta and United Airlines. With an average price for the route of $627 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $801 and an overall rating of 7.4.

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

    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 Chicago O'Hare Airport to Winnipeg.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago O'Hare Airport 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 Chicago O'Hare Airport to Winnipeg?

    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 Winnipeg with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and YWG 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 Chicago O'Hare Airport to Winnipeg?

    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 Winnipeg from Chicago O'Hare Airport 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 ORD to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for $878 or less round-trip.

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

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 3 airlines serving from O'Hare Intl to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. 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 O'Hare Intl to Winnipeg? 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 11004 reviews
8.2boarding
7.9comfort
8.0entertainment
7.5food
8.6crew
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

All good, useful to have the united app from check in to boarding

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

The flight was very uncomfortable and there was no snacks served for the 13 hours international flight. In addition, the flight was delayed 3 hours

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

Cabin crew were great. Seats are criminal for tall people

Flight was delayed 1.5 hrs due to problem with a previous flight to mine; I was informed appropriately via Text & Email, however, website did not keep up with messages sent by nearly an hour. When checking-in warm & friendly reception at check-in desk until female Air Canada Rep noticed my flight number and instantly pivoted to a condescending & sarcastic comments about getting my bag checked in since I’m running so late; then tone instantly changed again few minutes later when she muttered, “Oh, they’ve delayed it” another sign systems & worse front line staff, not fully informed or simply not reading their flight status updates. Flight crew were very friendly & did a great job trying to make up lost time due to the delay.

It was great, love the experience and will definitely recommend 👌. Communication was great

My flight was great! Gate attendants and crew were great… pleasant and in good spirits. Flight delayed several hours and we were well informed of the status while on plane. Thank you!

The fact that I got to Toronto alive and well and safe is a huge plus. I thank the captain and crew for a safe flight The comfort of the aircraft leaves much to be desired. Human beings should not have to be that cramped and squashed on a flight that we pay a lot for and even have to pay for lousy food choices The cabin crew were pleasant and helpful Kudos to them as the flight was packed to capacity and there was a lot of work for them in a short space of time All in all a good experience, but too cramped

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

The late departure Of two hours waitresses, immature, and gossiping

We had a good flight, service was good and lots of leg room. Service was good and the staff were friendly.

Book cheap flights from Chicago to Winnipeg

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Winnipeg found on KAYAK in the last 72 hours.
7/21Sun
3 stops
15h 12mORD-YWG
$195
7/23Tue
1 stopDelta
7h 28mORD-YWG
$219
7/4Thu
2 stops
12h 29mORD-YWG
$222
7/23Tue
2 stopsDelta
10h 00mORD-YWG
$224
7/22Mon
1 stopWestJet
23h 17mORD-YWG
$229
7/22Mon
1 stopWestJet
17h 43mORD-YWG
$233
7/4Thu
nonstopAir Canada
2h 26mORD-YWG
$403
7/21Sun
nonstopUnited Airlines
2h 26mORD-YWG
$546
7/23Tue
nonstopUnited Airlines
2h 26mORD-YWG
$666
7/22Mon
nonstopAir Canada
2h 26mORD-YWG
$682

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Chicago O'Hare Airport - Winnipeg Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago O'Hare Airport

Cabin classes:

$862

Browse destinations: