YWG - CHI

$123 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 1/12. 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
$206
Typical prices: $515-$642
Multiple Airlines
mar. 1/13mar. 1/20
YWG - ORD • 2 stops
Cheapest non-stop
$489
Typical prices: $465-$546
United Airlines
jue. 2/26dom. 3/1
YWG - ORD • 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'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 • 20% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
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Flight Deals
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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

mar., ene. 13 - mar., ene. 20
Multiple Airlines Logo
9:00 pm - 4:52 pm
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 pm - 3:07 pm
ORD
-
YWG
24h 14m1 stop
$206Multiple Airlines
mié., ene. 14 - lun., ene. 19
Multiple Airlines Logo
12:55 pm - 11:47 am
YWG
-
MDW
22h 52m2 stops
Multiple Airlines Logo
12:57 pm - 12:43 am
MDW
-
YWG
11h 46m1 stop
$210Multiple Airlines
vie., ene. 30 - vie., feb. 6
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m1 stop
$214WestJet
mié., ene. 14 - lun., ene. 19
Multiple Airlines Logo
7:30 am - 4:52 pm
YWG
-
ORD
9h 22m1 stop
Multiple Airlines Logo
11:48 am - 12:43 am
ORD
-
YWG
12h 55m1 stop
$218Multiple Airlines
mar., ene. 13 - mar., ene. 20
Multiple Airlines Logo
9:00 pm - 4:52 pm
YWG
-
ORD
19h 52m2 stops
Multiple Airlines Logo
2:53 pm - 3:07 pm
ORD
-
YWG
24h 14m1 stop
$221Multiple Airlines
vie., ene. 16 - dom., ene. 18
Multiple Airlines Logo
5:05 pm - 4:52 pm
YWG
-
ORD
23h 47m1 stop
Multiple Airlines Logo
8:41 pm - 12:43 am
ORD
-
YWG
28h 02m1 stop
$232Multiple Airlines
sáb., abr. 25 - jue., abr. 30
WestJet Logo
12:40 pm - 4:43 pm
YWG
-
ORD
28h 03m1 stop
WestJet Logo
5:30 pm - 5:40 pm
ORD
-
YWG
24h 10m1 stop
$234WestJet
vie., ene. 30 - vie., feb. 6
Multiple Airlines Logo
4:10 pm - 4:51 pm
YWG
-
ORD
24h 41m2 stops
Multiple Airlines Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m1 stop
$237Multiple Airlines
sáb., abr. 25 - jue., abr. 30
WestJet Logo
5:00 pm - 4:43 pm
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 pm - 2:30 pm
ORD
-
YWG
21h 00m1 stop
$239WestJet
sáb., abr. 25 - jue., abr. 30
WestJet Logo
5:00 pm - 4:43 pm
YWG
-
ORD
23h 43m2 stops
WestJet Logo
5:30 pm - 11:00 pm
ORD
-
YWG
29h 30m1 stop
$240WestJet
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 January.

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 $273 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 Thursday and more expensive on a Sunday. On your return trip to Winnipeg, you should consider flying back on a Thursday, and avoid Mondays 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 December and April, where the average cost of round-trip tickets is $602 and $473 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 2 stops layover the cheapest option at $448 on average.

Find deals
Expert advice

Expert advice for your flight from Winnipeg to Chicago

 
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.
Airlines
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
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.

Read more about United AirlinesBy Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and United Airlines

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 seasonJanuary
Cheapest flight$123
Best time to beat the crowds but there is an average 7% increase in price.
Flight from Winnipeg to Chicago O'Hare 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 $123 for a one-way ticket and $206 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, Delta, Air France, Virgin Atlantic, 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.

  • 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 $362 or less one-way and $384 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 airline 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 9091 reviews
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)