YWG - CHI

$148 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 7/22. 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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Flights 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

Fri, Sep 12 - Sun, Sep 14
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$241WestJet
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Fri, Aug 22 - Wed, Sep 3
WestJet Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
WestJet Logo
1:40 pm - 9:25 pmORD-YWG
7h 45m1 stop
$267WestJet
Find Deal
Fri, Sep 12 - Mon, Sep 15
 Logo
9:00 am - 4:18 pmYWG-ORD
7h 18m1 stop
 Logo
5:13 pm - 12:13 amORD-YWG
31h 00m2 stops
Mon, Sep 8 - Thu, Sep 11
 Logo
6:30 am - 10:28 pmYWG-ORD
15h 58m2 stops
 Logo
3:29 pm - 3:55 pmORD-YWG
24h 26m2 stops
Fri, Jul 18 - Sat, Jul 19
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
9:32 pm - 1:09 pmORD-YWG
15h 37m1 stop
$454United Airlines
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Fri, Sep 19 - Tue, Sep 23
Delta Logo
12:40 pm - 6:07 pmYWG-MDW
5h 27m1 stop
Delta Logo
1:00 pm - 11:32 pmMDW-YWG
10h 32m2 stops
$454Delta
Find Deal
Mon, Sep 8 - Thu, Sep 11
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
$455United Airlines
Find Deal
Tue, Jul 29 - Tue, Aug 5
Air Canada Logo
5:00 am - 1:13 pmYWG-ORD
8h 13m1 stop
Air Canada Logo
9:55 am - 5:40 pmORD-YWG
7h 45m1 stop
$467Air Canada
Find Deal
Fri, Aug 22 - Wed, Sep 3
Delta Logo
8:35 am - 5:37 pmYWG-MDW
9h 02m1 stop
Delta Logo
9:30 am - 8:11 pmMDW-YWG
10h 41m2 stops
$471Delta
Find Deal
Fri, Jul 18 - Sat, Jul 19
Air Canada Logo
5:00 am - 1:13 pmYWG-ORD
8h 13m1 stop
Air Canada Logo
9:55 am - 5:40 pmORD-YWG
7h 45m1 stop
$491Air Canada
Find Deal
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Winnipeg to Chicago.

Our data shows that the cheapest route for a return flight from Winnipeg to Chicago cost $192 and was between Winnipeg (YWG) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $192.

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 Wednesday and more expensive on a Sunday. On your return trip to Winnipeg, you should consider flying back on a Friday, and avoid Sundays 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 June, where tickets cost $408 (return) on average. On the other hand, the most expensive months are April and September, where the average cost of round-trip tickets is $517 and $481 respectively.

How far in advance should I book a flight from Winnipeg to Chicago?

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, 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, you should book around 7 weeks before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
High seasonDecember
Cheapest flight$148
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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 $148 for a one-way ticket and $241 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: WestJet, Delta, Virgin Atlantic, KLM, Air France, and Air Canada.

  • 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 $535 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 $426 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 $227 or less one-way and $433 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

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 8801 reviews
8.1Crew
7.0Entertainment
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

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.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

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.

So far so good but food and entertainment are not available for this flight

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

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.

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.

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

Information on your arrival and departure airports

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