CHI - YWG

$75 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 11/27. 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 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

Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
7:23 pm - 12:41 amMDW-YWG
29h 18m2 stops
Multiple Airlines Logo
7:30 am - 9:52 amYWG-MDW
26h 22m1 stop
$193Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
7:23 pm - 3:07 pmMDW-YWG
19h 44m1 stop
Multiple Airlines Logo
7:30 am - 9:52 amYWG-MDW
26h 22m1 stop
$196Multiple Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
Multiple Airlines Logo
2:49 pm - 3:07 pmMDW-YWG
24h 18m1 stop
Multiple Airlines Logo
7:30 am - 7:42 pmYWG-MDW
12h 12m1 stop
$203Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
5:05 am - 12:41 amORD-YWG
19h 36m2 stops
Multiple Airlines Logo
7:30 am - 10:24 pmYWG-ORD
14h 54m1 stop
$228Multiple Airlines
Find Deal
Fri, Jan 9 - Mon, May 4
WestJet Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$360WestJet
Find Deal
Fri, Jan 9 - Sat, May 2
WestJet Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
WestJet Logo
12:40 pm - 4:48 pmYWG-ORD
4h 08m1 stop
$378WestJet
Find Deal
Mon, Dec 29 - Sun, Apr 26
WestJet Logo
6:30 pm - 11:44 pmORD-YWG
5h 14m1 stop
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
$383WestJet
Find Deal
Tue, Dec 30 - Fri, May 1
Delta Logo
5:05 pm - 11:45 amMDW-YWG
18h 40m2 stops
Delta Logo
12:40 pm - 6:05 pmYWG-MDW
5h 25m1 stop
$541Delta
Find Deal
Tue, Dec 30 - Sat, Apr 25
Delta Logo
5:05 pm - 11:45 amMDW-YWG
18h 40m2 stops
Delta Logo
12:40 pm - 9:45 pmYWG-MDW
9h 05m2 stops
$546Delta
Find Deal
Wed, Jan 7 - Tue, May 5
Delta Logo
9:50 am - 11:38 pmMDW-YWG
13h 48m1 stop
Delta Logo
12:40 pm - 6:05 pmYWG-MDW
5h 25m1 stop
$565Delta
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
$193
Multiple Airlines
Thu 12/4Sun 12/7
MDW - YWG • 2 stops
Cheapest non-stop
$614
Typical prices: $268-$613
Air Canada
Thu 12/4Sun 12/7
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!
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.

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

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

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 $617 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 Thursdays 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.

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 $609 on average.

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

Good to know

Low seasonApril
Cheapest flight$75
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 O'Hare 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 $75 for a one-way ticket and $193 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 $616 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 $500 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.

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 8999 reviews
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

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

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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.

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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