YWG - ORD

C$ 179 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 15/9. 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

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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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

Mon, 29 Sep - Mon, 6 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
C$ 285WestJet
Find Deal
Sun, 19 Oct - Thu, 23 Oct
 Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
 Logo
1:26 p.m. - 3:55 p.m.ORD-YWG
26h 29m1 stop
C$ 301
Find Deal
Mon, 22 Sep - Fri, 26 Sep
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:41 a.m.ORD-YWG
18h 11m1 stop
C$ 312WestJet
Find Deal
Sat, 18 Oct - Thu, 23 Oct
 Logo
6:30 a.m. - 4:43 p.m.YWG-ORD
10h 13m1 stop
 Logo
1:26 p.m. - 3:55 p.m.ORD-YWG
26h 29m1 stop
C$ 320
Find Deal
Sat, 13 Sep - Sat, 20 Sep
 Logo
9:10 a.m. - 9:58 p.m.YWG-ORD
12h 48m1 stop
 Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 329
Find Deal
Sun, 19 Oct - Thu, 23 Oct
 Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
 Logo
1:26 p.m. - 12:13 a.m.ORD-YWG
10h 47m2 stops
C$ 331
Find Deal
Thu, 18 Sep - Sun, 21 Sep
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
1:01 p.m. - 3:31 p.m.ORD-YWG
2h 30mdirect
C$ 460United Airlines
Find Deal
Thu, 18 Sep - Sun, 21 Sep
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
7:54 p.m. - 10:33 p.m.ORD-YWG
2h 39mdirect
C$ 463United Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
United Airlines Logo
7:54 p.m. - 10:33 p.m.ORD-YWG
2h 39mdirect
C$ 473United Airlines
Find Deal
Wed, 10 Sep - Sat, 13 Sep
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
United Airlines Logo
7:15 a.m. - 1:09 p.m.ORD-YWG
5h 54m1 stop
C$ 474United Airlines
Find Deal
Expert advice

Expert advice for your flight from Winnipeg to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation 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 original 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
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.

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
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 United Airlines, Air Canada 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
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 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 August, where tickets cost C$ 510 (return) on average. On the other hand, the most expensive months are September and November, where the average cost of round-trip tickets is C$ 722 and C$ 702 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 566 on average.

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 6 weeks before departure, which saves you about 56% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonMarch
Cheapest flightC$ 179
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 18% 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$ 130 for a one-way ticket and C$ 207 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: Delta, Virgin Atlantic, KLM, Air France, Air Canada, and WestJet.

  • 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$ 674 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$ 458 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$ 515 or less one-way and C$ 563 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

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, +2 more

Air Canada,Air New Zealand, +3 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

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 8915 reviews
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

Our flight schedule was changed over six times, ultimately leaving us with a layover much shorter than we originally booked, which meant a panicked run through the airport. And the entertainment screen didn't function. As I've come to expect with Delta, a very mediocre and not customer-focused experience. This is on top of an outbound flight that was so delayed by mechanical issues, we had to spend the night at our layover city.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

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.

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.

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

Information on your arrival and departure airports

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