CHI - YWG

$87 Find Cheap Flights from Chicago to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 11/2. 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 Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, 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 Chicago to Winnipeg, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Winnipeg (CHI-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Winnipeg 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 Chicago to Winnipeg

Mon, Oct 6 - Sun, Oct 12
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$208WestJet
Find Deal
Thu, Oct 9 - Sun, Oct 12
WestJet Logo
5:30 pm - 11:10 pmORD-YWG
29h 40m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$211WestJet
Find Deal
Mon, Oct 6 - Fri, Oct 17
WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$214WestJet
Find Deal
Fri, Oct 10 - Sun, Oct 12
WestJet Logo
5:30 pm - 11:41 amORD-YWG
18h 11m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$215WestJet
Find Deal
Thu, Oct 30 - Fri, Oct 31
Multiple Airlines Logo
6:20 am - 12:41 amMDW-YWG
18h 21m2 stops
Multiple Airlines Logo
7:30 am - 6:39 pmYWG-MDW
11h 09m1 stop
$216Multiple Airlines
Find Deal
Sat, Oct 11 - Fri, Oct 17
WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$216WestJet
Find Deal
Sun, Oct 12 - Fri, Oct 17
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$218WestJet
Find Deal
Wed, Oct 29 - Fri, Oct 31
Delta Logo
9:20 am - 11:30 amMDW-YWG
26h 10m1 stop
Delta Logo
5:40 pm - 8:40 amYWG-MDW
15h 00m2 stops
$497Delta
Find Deal
Wed, Oct 29 - Fri, Oct 31
Delta Logo
9:20 am - 11:30 amMDW-YWG
26h 10m1 stop
Delta Logo
12:20 pm - 1:08 pmYWG-MDW
24h 48m1 stop
$539Delta
Find Deal
Fri, Oct 31 - Wed, Nov 5
Delta Logo
3:00 pm - 11:27 pmMDW-YWG
8h 27m1 stop
Delta Logo
12:20 pm - 10:14 pmYWG-MDW
9h 54m2 stops
$652Delta
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 provides priority check-in for elite travelers.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
ORD-YWG
Cheapest
ORD-YWG
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 50% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$208
Overall average: $632
WestJet
Mon 10/6Sun 10/12
ORD - YWG • 1 stop
Cheapest non-stop
$415
Typical prices: $542-725
United Airlines
Tue 10/7Mon 10/13
ORD - YWG • 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 Winnipeg!
Expert advice

Expert advice for your flight from Chicago to Winnipeg

 
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 offers Priority Boarding for purchase, placing you in Zone 2 for boarding.


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

Air Canada

Air Canada offers priority check-in for higher fare classes and elite status travelers.


Preferred Economy seats provide up to four extra inches of legroom for a fee.

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 Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Winnipeg flight route?

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

The cheapest return flight from Chicago to Winnipeg costs $415 on the route between Chicago O'Hare Intl Airport (ORD) and Winnipeg (YWG). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

The average price of all round-trip flights from Chicago to Winnipeg clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Winnipeg, look for departures on Saturdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Winnipeg, Friday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Winnipeg, 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 Chicago to Winnipeg is May, where tickets cost $271 (return) on average. On the other hand, the most expensive months are February and July, where the average cost of round-trip tickets is $752 and $628 respectively.

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

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 $554, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$87
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to Winnipeg

When to book flights from Chicago to Winnipeg

Are your dates flexible? Find out the best times to travel from Chicago to Winnipeg 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 Chicago to Winnipeg

  • What is the cheapest flight from Chicago to Winnipeg?

    In the last 3 days, the lowest price for a flight from Chicago to Winnipeg was $87 for a one-way ticket and $208 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Winnipeg.

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

    On your way to Winnipeg, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Winnipeg.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

  • Which aircraft models fly most regularly from Chicago to Winnipeg?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

  • Which airline alliances offer flights from Chicago to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

  • On which days can I fly direct from Chicago to Winnipeg?

    There are nonstop flights from Chicago to Winnipeg on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Winnipeg are United Airlines and Air Canada. With an average price for the route of $615 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 $523 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Chicago to Winnipeg?

    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 Chicago to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago 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 Chicago to Winnipeg?

    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 Winnipeg with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

    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 Winnipeg from Chicago 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 Chicago to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for $415 or less round-trip.

Prefer to fly direct from Chicago to Winnipeg?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Winnipeg.
Find which airlines fly direct from Chicago to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Chicago to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. 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 Chicago to Winnipeg? 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
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Because of a change in aircraft, I was unable to experience the business class I paid for and was disappointed.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Very clean plane, staff were courteous, complimentary wifi and beverages are nice, and it was nice to have a whole row to myself! I do miss having seatback entertainment, though. And the prices are getting ridiculous, especially with the different teared tickets. But the flight overall was great.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

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

Information on your arrival and departure airports

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