YWG - ORD

C$ 150 Find Cheap Flights from Winnipeg to Chicago

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 Chicago departing on 16/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl 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
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Cheap Flight Deals from Winnipeg to Chicago (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 Chicago 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.

Recent round-trip flight deals from Winnipeg to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
WestJet Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
WestJet Logo
5:30 p.m. - 5:41 p.m.ORD-YWG
24h 11m1 stop
C$ 269WestJet
Find Deal
Tue, 3 Jun - Tue, 10 Jun
WestJet Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
WestJet Logo
5:30 p.m. - 9:34 p.m.ORD-YWG
28h 04m1 stop
C$ 276WestJet
Find Deal
Tue, 13 May - Fri, 16 May
 Logo
9:00 a.m. - 4:38 p.m.YWG-ORD
7h 38m1 stop
 Logo
5:01 a.m. - 4:23 p.m.ORD-YWG
11h 22m1 stop
C$ 352
Find Deal
Tue, 22 Jul - Wed, 6 Aug
 Logo
9:00 a.m. - 4:41 p.m.YWG-ORD
7h 41m1 stop
 Logo
6:20 a.m. - 4:28 p.m.ORD-YWG
10h 08m1 stop
C$ 389
Find Deal
Tue, 13 May - Fri, 16 May
Delta Logo
12:52 p.m. - 7:20 p.m.YWG-ORD
6h 28m1 stop
Delta Logo
1:45 p.m. - 11:25 p.m.ORD-YWG
9h 40m2 stops
C$ 483Delta
Find Deal
Fri, 23 May - Wed, 28 May
Air Canada Logo
11:00 a.m. - 8:12 p.m.YWG-ORD
9h 12m1 stop
Air Canada Logo
2:00 p.m. - 9:07 p.m.ORD-YWG
7h 07m1 stop
C$ 485Air Canada
Find Deal
Tue, 27 May - Wed, 28 May
Air Canada Logo
7:40 a.m. - 3:05 p.m.YWG-ORD
7h 25m1 stop
Air Canada Logo
9:35 a.m. - 5:35 p.m.ORD-YWG
8h 00m1 stop
C$ 493Air Canada
Find Deal
Wed, 28 May - Fri, 30 May
Delta Logo
5:35 p.m. - 9:21 p.m.YWG-ORD
3h 46m1 stop
Delta Logo
1:45 p.m. - 11:25 p.m.ORD-YWG
9h 40m2 stops
C$ 505Delta
Find Deal
Fri, 23 May - Wed, 28 May
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
1:02 p.m. - 3:31 p.m.ORD-YWG
2h 29mdirect
C$ 579United Airlines
Find Deal
Fri, 23 May - Fri, 30 May
United Airlines Logo
4:25 p.m. - 12:25 a.m.YWG-ORD
8h 00m1 stop
United Airlines Logo
5:02 a.m. - 1:09 p.m.ORD-YWG
8h 07m1 stop
C$ 587United Airlines
Find Deal
Thu, 5 Jun - Sun, 8 Jun

Expert advice for your flight from Winnipeg to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are specific to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Air Canada

Air Canada offers priority boarding for Business Class and elite status passengers, enhancing travel efficiency.


Air Canada provides Wi-Fi on select flights, with free messaging for Aeroplan members.

Read more about Air Canadaby Stefanie Waldek
United Airlines

United offers Priority Boarding for Zone 2, ensuring overhead bin space for carry-ons.


United's Wi-Fi varies; T-Mobile customers get free streaming on flights.

Airports
YWG

Security at YWG is efficient, with quick-moving lines. Two screening areas are available for domestic/international and U.S. flights.

Read more about YWGby Mark Stachiew
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada, United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Stachiew

Mark Stachiew

Expert on YWG

Mark Stachiew

Mark Stachiew

Mark Stachiew has been exploring the world and writing about it for more than 30 years. His travel stories have appeared in numerous newspapers, magazines and online publications in Canada, the United States and beyond.

Read more

KAYAK's insights & trends for Winnipeg to Chicago flights

Get data-powered insights and trends into flights from Winnipeg to Chicago 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?

The average price of all round-trip 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, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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 round-trip 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 January, where tickets cost C$ 572 (return) on average. On the other hand, the most expensive months are May and June, where the average cost of round-trip tickets is C$ 961 and C$ 796 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.
To get a below average price on the flight from Winnipeg to Chicago O'Hare Intl Airport, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low season

March

High season

May

Cheapest flight

C$ 150
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly (35% more expensive on average)
Flight from Winnipeg to Chicago

When to book flights from Winnipeg to Chicago

Are your dates flexible? Find out the best times to travel from Winnipeg to Chicago 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 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 C$ 108 for a one-way ticket and C$ 194 for a round-trip.

  • Which airports will I be using when flying from Winnipeg to Chicago?

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

  • Which airlines offer Wi-Fi service onboard planes from Winnipeg to Chicago?

    All the following airlines offer inflight Wi-Fi service on the Winnipeg to Chicago flight route: WestJet, Air Canada, Virgin Atlantic, KLM, Delta, and Air France.

  • Which aircraft models fly most regularly from Winnipeg to Chicago?

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

  • Which airline alliances offer flights from Winnipeg to Chicago?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Chicago.

  • On which days can I fly direct from Winnipeg to Chicago?

    There are direct flights from Winnipeg to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Winnipeg to Chicago are United Airlines and WestJet. With an average price for the route of C$ 715 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 961 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Winnipeg to Chicago?

    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.

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

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

  • What is the Hacker Fare option on flights from Winnipeg to Chicago?

    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 with an airline and back to Winnipeg with another airline.

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

    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 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 C$ 190 or less one-way and C$ 591 or less round-trip.

Prefer to fly direct from Winnipeg to Chicago?

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

Direct departures

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Tuesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Wednesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Saturday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Sunday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Tuesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Wednesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Saturday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Sunday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

See more nonstop flights
See more nonstop flights

Top 3 airlines serving from Winnipeg to Chicago

 
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 Chicago? 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.
7.4
United AirlinesOverall score based on 8685 reviews
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
Airline reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

10.0 ExcellentDr. Joseph, Apr 2025IAH - ORD
Read more United Airlines reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

it's all good nothing you can do make better 😌

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

It was so bad experience they wanted just charged passengers for any reason.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Ok Did not like that the second leg of flight was moved earlier making it a rush to make it

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything you need to know for your flight from Winnipeg to Chicago

Information on your arrival and departure airports

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