YWG - CHI

$172 Find Cheap Flights from Winnipeg to Chicago - Compare and Save

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 10/25. 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

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$303
Typical prices: $394-$352
WestJet
Fri 9/25Sun 9/27
YWG - ORD • 1 stop
Cheapest non-stop
$664
Typical prices: $1,338-$881
United Airlines
Wed 10/21Sat 10/24
YWG - ORD • Non-stop
Top airlines
Cheapest • from $303 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 34m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $290 (round-trip)
Shortest trip • 4h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 63% price drop
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 Chicago!
Flight Deals
Booking Insights
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

Fri, Sep 25 - Sun, Sep 27
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$303WestJet
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
11:15 am - 11:00 am
YWG
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
3:20 pm - 9:45 am
ORD
-
YWG
18h 25m
1 stop
$335Multiple Airlines
Tue, Sep 1 - Tue, Sep 8
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$337WestJet
Sun, Sep 13 - Mon, Sep 14
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
7:00 am - 5:58 pm
ORD
-
YWG
10h 58m
2 stops
$345Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
8:45 pm - 11:00 am
YWG
-
ORD
14h 15m
1 stop
Multiple Airlines Logo
3:20 pm - 9:45 am
ORD
-
YWG
18h 25m
1 stop
$348Multiple Airlines
Fri, Oct 2 - Sun, Oct 4
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$364WestJet
Tue, Sep 1 - Tue, Sep 8
Multiple Airlines Logo
11:15 am - 11:00 am
YWG
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$368Multiple Airlines
Fri, Jul 17 - Sun, Jul 19
Multiple Airlines Logo
10:45 am - 8:29 pm
YWG
-
ORD
9h 44m
1 stop
Multiple Airlines Logo
5:35 pm - 10:43 am
ORD
-
YWG
17h 08m
2 stops
$369Multiple Airlines
Fri, Jul 17 - Sun, Jul 19
Porter Airlines Logo
11:40 am - 9:40 am
YWG
-
MDW
22h 00m
2 stops
Porter Airlines Logo
3:20 pm - 5:58 pm
MDW
-
YWG
26h 38m
2 stops
$552Porter Airlines
Wed, Oct 21 - Sat, Oct 24
Delta Logo
8:00 am - 8:45 am
YWG
-
MDW
24h 45m
2 stops
Delta Logo
6:00 am - 11:34 pm
MDW
-
YWG
17h 34m
2 stops
$569Delta
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 September.

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 $362 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 Saturday and more expensive on a Sunday. On your return trip to Winnipeg, you should consider flying back on a Friday, 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 October, where tickets cost $80 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $447 and $314 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.

No, with an average price for the route of $403, prices are generally cheapest when you fly direct.

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.
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.

Good to know

Low seasonJune
Cheapest flight$172
Best time to beat the crowds with an average 60% drop in price.
Most popular time to fly and prices are also 14% lower on average.
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 5 days, the lowest price for a flight from Winnipeg to Chicago was $172 for a one-way ticket and $303 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?

    Only Air Canada offers inflight Wi-Fi service on the Winnipeg to Chicago flight route.

  • 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 $274 or less one-way and $512 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 9859 reviews
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

2.0 MediocreGreg, Jun 2026
YYZ - ORD
Read more United Airlines reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

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

Information on your arrival and departure airports