CHI - YWG

$90 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 6/3. 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
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
$213
WestJet
Fri 5/15Mon 5/18
ORD - YWG • 1 stop
Cheapest non-stop
$666
Typical prices: $320-$648
Air Canada
Thu 3/5Sun 3/8
ORD - YWG • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 • 57% price drop
July
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 Winnipeg!
Flight Deals
Booking Insights
Expert advice
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

Fri, May 15 - Mon, May 18
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$213WestJet
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
4:42 pm - 3:09 pm
ORD
-
YWG
22h 27m
1 stop
Multiple Airlines Logo
9:00 pm - 6:41 pm
YWG
-
ORD
21h 41m
2 stops
$234Multiple Airlines
Fri, May 15 - Sun, May 17
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$235WestJet
Fri, Feb 27 - Fri, Mar 6
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
$241WestJet
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
4:42 pm - 3:09 pm
ORD
-
YWG
22h 27m
1 stop
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
$253Multiple Airlines
Tue, Mar 3 - Wed, Mar 4
Multiple Airlines Logo
9:15 am - 12:41 am
ORD
-
YWG
15h 26m
2 stops
Multiple Airlines Logo
7:30 am - 4:52 pm
YWG
-
ORD
9h 22m
1 stop
$258Multiple Airlines
Tue, Mar 3 - Wed, Mar 4
Multiple Airlines Logo
9:15 am - 12:41 am
ORD
-
YWG
15h 26m
2 stops
Multiple Airlines Logo
7:30 am - 4:52 pm
YWG
-
ORD
9h 22m
1 stop
$263Multiple Airlines
Fri, May 15 - Sun, May 17
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
6:00 am - 4:40 pm
YWG
-
ORD
10h 40m
1 stop
$264WestJet
Fri, Feb 27 - Fri, Mar 6
Multiple Airlines Logo
2:20 pm - 12:07 pm
ORD
-
YWG
21h 47m
2 stops
Multiple Airlines Logo
7:30 am - 11:16 am
YWG
-
ORD
27h 46m
1 stop
$275Multiple Airlines
Fri, May 15 - Sun, May 17
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
10:15 pm - 4:40 pm
YWG
-
ORD
18h 25m
2 stops
$278WestJet
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 $973 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, Thursday 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 January and February, where the average cost of round-trip tickets is $1,231 and $752 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 $771 on average.

Expert advice

Expert advice for your flight from Chicago to Winnipeg

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Air Canada

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.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 12% drop 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 $90 for a one-way ticket and $213 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 $630 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 $562 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 $976 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 9219 reviews
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

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