CHI - YWG

$97 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 5/26. 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 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$314
Typical prices: $584-$284
WestJet
Wed 5/27Tue 6/2
ORD - YWG • 1 stop
Cheapest non-stop
$777
Typical prices: $584-$230
Air Canada
Fri 5/29Mon 6/1
ORD - YWG • Non-stop
Advice from real travelers
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 airlines
WestJet
Cheapest • from $314 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 2h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
ORD
-
YWG
Cheapest
ORD
-
YWG
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Calgary (YYC)
Cheapest • Avg $358 (round-trip)
Minneapolis (MSP)
Shortest trip • 4h 47m (one-way)
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 80% 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

Wed, May 27 - Tue, Jun 2
WestJet Logo
5:30 pm - 12:15 pm
ORD
-
YWG
18h 45m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$314WestJet
Thu, Oct 15 - Mon, Oct 19
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
$337WestJet
Mon, Jun 8 - Thu, Jun 11
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
$341WestJet
Sun, Oct 11 - Wed, Oct 21
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
$352WestJet
Tue, Aug 18 - Tue, Aug 25
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
$361WestJet
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 pm - 7:55 am
YWG
-
ORD
34h 50m
2 stops
$362Multiple Airlines
Wed, Sep 2 - Sat, Sep 5
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
$387WestJet
Mon, Jun 1 - Sun, Jun 7
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
Multiple Airlines Logo
9:05 pm - 11:09 am
YWG
-
MDW
14h 04m
2 stops
$388Multiple Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:20 am - 4:18 pm
YWG
-
ORD
6h 58m
1 stop
$392Multiple Airlines
Thu, Jun 4 - Sun, Jun 7
Porter Airlines Logo
10:15 am - 7:49 pm
MDW
-
YWG
9h 34m
1 stop
Porter Airlines Logo
8:45 pm - 9:35 am
YWG
-
MDW
12h 50m
1 stop
$478Porter Airlines
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 May.

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 $687 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 Tuesdays and avoid leaving on a Monday, 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 February, where tickets cost $62 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $1,074 and $528 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 $685 on average.

Find deals
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 Air Canada and United Airlines

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$97
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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 $97 for a one-way ticket and $314 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.

  • 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 $624 or less one-way and $757 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 airline 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 9680 reviews
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

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

Information on your arrival and departure airports

Winnipeg (YWG)