YWG - CHI

$130 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 11/26. 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

 
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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$196
Multiple Airlines
Fri 12/5Mon 12/8
YWG - MDW • 1 stop
Cheapest non-stop
$491
Typical prices: $415-$665
United Airlines
Tue 3/3Sun 3/8
YWG - ORD • Non-stop
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 routes
YWG-ORD
Cheapest
YWG-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 19% 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 100s 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-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, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
7:30 am - 10:12 pmYWG-MDW
14h 42m1 stop
Multiple Airlines Logo
8:42 pm - 6:06 pmMDW-YWG
21h 24m2 stops
$196Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
7:30 am - 10:12 pmYWG-MDW
14h 42m1 stop
Multiple Airlines Logo
8:42 pm - 6:06 pmMDW-YWG
21h 24m2 stops
$198Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
7:30 am - 11:54 amYWG-ORD
28h 24m1 stop
Multiple Airlines Logo
10:24 am - 12:41 amORD-YWG
14h 17m2 stops
$198Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
7:30 am - 11:54 amYWG-ORD
28h 24m1 stop
Multiple Airlines Logo
6:11 am - 3:07 pmORD-YWG
8h 56m1 stop
$202Multiple Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 3
Multiple Airlines Logo
7:30 am - 12:08 amYWG-ORD
16h 38m1 stop
Multiple Airlines Logo
8:00 am - 12:41 amORD-YWG
16h 41m2 stops
$213Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
9:00 pm - 10:12 pmYWG-MDW
25h 12m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$214Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 1:52 pmORD-YWG
23h 32m2 stops
$323WestJet
Find Deal
Fri, Dec 5 - Mon, Dec 8
WestJet Logo
7:30 am - 6:43 pmYWG-ORD
11h 13m1 stop
WestJet Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
$380WestJet
Find Deal
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:43 pmYWG-ORD
21h 48m1 stop
WestJet Logo
5:30 pm - 11:40 amORD-YWG
18h 10m1 stop
$403WestJet
Find Deal
Wed, Dec 31 - Sat, May 2
Delta Logo
6:40 am - 10:22 pmYWG-MDW
15h 42m2 stops
Delta Logo
9:30 am - 4:54 pmMDW-YWG
7h 24m2 stops
$521Delta
Find Deal
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.

How much is a round-trip flight from Winnipeg to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Chicago departing in December.

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 $235 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 Thursday, 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 $354 (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 $483 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.

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

Good to know

Low seasonSeptember
Cheapest flight$130
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Winnipeg to Chicago Midway 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 $130 for a one-way ticket and $196 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 $491 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 $225 or less one-way and $454 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 8999 reviews
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
7.1Entertainment
Airline reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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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