YWG - CHI

$112 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 10/17. 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

 
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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Booking Insights
Flight Deals

Cheap Flights from Winnipeg to Chicago (YWG-CHI)

 
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

Sun, Oct 12 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$195WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:10 pmORD-YWG
29h 40m1 stop
$204WestJet
Find Deal
Fri, Oct 17 - Wed, Oct 29
Multiple Airlines Logo
9:00 am - 11:46 pmYWG-MDW
14h 46m1 stop
Multiple Airlines Logo
2:06 pm - 12:41 amMDW-YWG
34h 35m2 stops
$213Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
9:00 pm - 6:39 pmYWG-MDW
21h 39m2 stops
Multiple Airlines Logo
1:37 pm - 3:07 pmMDW-YWG
25h 30m1 stop
$218Multiple Airlines
Find Deal
Thu, Oct 9 - Sun, Oct 12
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
5:01 am - 1:09 pmORD-YWG
8h 08m1 stop
$343United Airlines
Find Deal
Sun, Oct 12 - Sun, Oct 19
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
5:01 am - 1:09 pmORD-YWG
8h 08m1 stop
$352United Airlines
Find Deal
Thu, Oct 9 - Sun, Oct 12
Delta Logo
6:40 am - 1:08 pmYWG-MDW
6h 28m1 stop
Delta Logo
9:20 am - 4:50 pmMDW-YWG
7h 30m1 stop
$447Delta
Find Deal
Tue, Mar 3 - Sun, Mar 8
Delta Logo
12:40 pm - 6:08 pmYWG-MDW
5h 28m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$553Delta
Find Deal
Thu, Oct 16 - Sun, Oct 26
Porter Airlines Logo
11:20 am - 8:39 amYWG-MDW
21h 19m2 stops
Porter Airlines Logo
4:15 pm - 11:13 amMDW-YWG
18h 58m2 stops
$618Porter Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
Porter Airlines Logo
4:25 pm - 11:50 amYWG-MDW
19h 25m2 stops
Porter Airlines Logo
11:00 am - 11:13 amMDW-YWG
24h 13m2 stops
$796Porter Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers six inches more legroom.
Air Canada's Preferred Economy adds four inches of legroom.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from $195 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YWG-ORD
Cheapest
YWG-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 18% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$195
Typical prices: $430-834
WestJet
Sun 10/12Sun 10/19
YWG - ORD • 1 stop
Cheapest non-stop
$352
Typical prices: $660-836
United Airlines
Sun 10/12Sun 10/19
YWG - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

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 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's Economy Plus offers up to six inches more legroom than standard economy seats.


Purchase Priority Boarding to ensure overhead bin space, placing you in Zone 2.

Air Canada

Air Canada's Preferred Economy seats offer up to four extra inches of legroom.


Check Wi-Fi availability on Air Canada's website five days before your flight.

Read more about Air Canadaby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Air Canada

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
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 is the cheapest Winnipeg to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Winnipeg to Chicago costs $232 on the route between Winnipeg (YWG) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Winnipeg, you should consider flying back on a Saturday, and avoid Wednesdays for better deals.

What is the cheapest month to fly from Winnipeg to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Chicago, 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 is September, where tickets cost $363 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is $495 and $482 respectively.

Can I save money by flying with a layover from Winnipeg to Chicago?

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 $385 on average.

Good to know

Low seasonJanuary
Cheapest flight$112
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Winnipeg to Chicago O'Hare Airport

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 flights from Winnipeg to Chicago

  • What is the cheapest flight from Winnipeg to Chicago?

    In the last 3 days, the lowest price for a flight from Winnipeg to Chicago was $112 for a one-way ticket and $195 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Chicago?

    Yes

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

    Winnipeg is served by only 1 airport and there are 2 airports in Chicago. You will leave Winnipeg from Winnipeg and you will be arriving in Chicago at one of these airports: Chicago Midway or 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: Air Canada, KLM, Virgin Atlantic, Delta, Air France, 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 nonstop flights from Winnipeg to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Winnipeg to Chicago are United Airlines and Air Canada. With an average price for the route of $549 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of $495 and an overall rating of 7.1.

  • 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 travelers 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $247 or less one-way and $466 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.
Find which airlines fly direct from Winnipeg Airport to Chicago, which days they fly and book direct flights.

Direct departures

Winnipeg to Chicago

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 direct flights

Direct returns

Chicago 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 direct flights

Reviews of the top 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 8929 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

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.

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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