YWG - ORD

C$ 190 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 12/5. 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
1 adult, Economy, 0 bags

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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Everything you should know

Cheapest round-trip
C$ 357
Overall average: C$ 678
WestJet
Fri 22/5Fri 29/5
YWG - ORD • 1 stop
Cheapest direct flights
C$ 791
Typical prices: C$ 654-C$ 853
United Airlines
Thu 23/4Thu 30/4
YWG - ORD • Direct
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Priority Boarding ensures carry-on space.
Security at Winnipeg is efficient with quick lines.
Expert advice
Expert advice
Expert advice
Expert advice
Direct flights
Every day
You can fly direct with United Airlines. Average duration is 2h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
September
Cheapest • 26% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Chicago

Fri, 22 May - Fri, 29 May
WestJet Logo
6:00 a.m. - 4:40 p.m.
YWG
-
ORD
10h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 357WestJet
Tue, 28 Apr - Fri, 1 May
Multiple Airlines Logo
9:05 p.m. - 10:02 a.m.
YWG
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 361Multiple Airlines
Tue, 28 Apr - Thu, 30 Apr
Multiple Airlines Logo
9:05 p.m. - 10:02 a.m.
YWG
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 366Multiple Airlines
Fri, 22 May - Fri, 29 May
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
2 stops
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 399WestJet
Wed, 15 Apr - Thu, 16 Apr
Multiple Airlines Logo
7:30 a.m. - 5:00 p.m.
YWG
-
ORD
9h 30m
1 stop
Multiple Airlines Logo
11:28 a.m. - 3:09 p.m.
ORD
-
YWG
27h 41m
1 stop
C$ 412Multiple Airlines
Tue, 28 Apr - Thu, 30 Apr
Multiple Airlines Logo
12:10 p.m. - 8:20 p.m.
YWG
-
ORD
8h 10m
1 stop
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 415Multiple Airlines
Mon, 20 Apr - Mon, 27 Apr
Multiple Airlines Logo
9:00 p.m. - 5:00 p.m.
YWG
-
ORD
20h 00m
2 stops
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 425Multiple Airlines
Wed, 22 Apr - Sat, 25 Apr
Multiple Airlines Logo
7:30 a.m. - 5:00 p.m.
YWG
-
ORD
9h 30m
1 stop
Multiple Airlines Logo
4:28 p.m. - 8:15 p.m.
ORD
-
YWG
27h 47m
2 stops
C$ 433Multiple Airlines
Wed, 15 Apr - Thu, 16 Apr
Multiple Airlines Logo
7:30 a.m. - 5:00 p.m.
YWG
-
ORD
9h 30m
1 stop
Multiple Airlines Logo
12:16 p.m. - 3:09 p.m.
ORD
-
YWG
26h 53m
2 stops
C$ 442Multiple Airlines
Tue, 28 Apr - Thu, 30 Apr
Multiple Airlines Logo
4:55 p.m. - 10:23 a.m.
YWG
-
ORD
17h 28m
3 stops
Multiple Airlines Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 449Multiple Airlines
Booking Insights

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 Friday 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 September, where tickets cost C$ 479 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is C$ 761 and C$ 758 respectively.

Can I save money by flying with a layover from Winnipeg to Chicago O'Hare Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 517, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Winnipeg to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Air Canada and ORD

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.

Mark Stachiew

Mark Stachiew

Expert on YWG

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.

Good to know

Low seasonFebruary
Cheapest flightC$ 190
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 22% lower 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$ 190 for a one-way ticket and C$ 357 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?

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

  • 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$ 637 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$ 383 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.

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$ 336 or less one-way and C$ 541 or less round-trip.

Prefer to fly direct from Winnipeg to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Winnipeg to Chicago O'Hare Intl.
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

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Winnipeg

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more nonstop flights

Reviews of the top 3 airlines flying 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 9408 reviews
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
8.1Crew
Airline reviews

They never clean the toilet, and the food is worse

4.0 OkayAnonymous, Mar 2026
HND - ORD
Read more United Airlines reviews

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

I like the fact air Canada is on time The food you guys serve is not good

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Upgraded to sit at the exit door so good leg room.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

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.

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

Information on your arrival and departure airports