YWG - ORD

$178 Find Cheap Flights from Winnipeg to Chicago O'Hare Airport

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 O'Hare Intl departing on 9/22. 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 O'Hare Intl Airport

 
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
$364
Typical prices: $881-$354
WestJet
Fri 10/2Sun 10/4
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
WestJet
Cheapest • from $364 (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 34m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg $360 (round-trip)
Minneapolis (MSP)
Shortest trip • 4h 54m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 35% price drop
August
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 O'Hare Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Winnipeg to O'Hare Intl (YWG-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to O'Hare Intl 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 O'Hare Intl

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
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
Multiple Airlines Logo
3:20 pm - 5:58 pm
ORD
-
YWG
26h 38m
2 stops
$369Multiple Airlines
Fri, Sep 4 - Sat, Sep 26
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
$370Multiple Airlines
Thu, Sep 17 - Sat, Sep 19
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
$372Multiple Airlines
Sun, Sep 6 - Mon, Sep 28
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
$373WestJet
Sat, Oct 31 - Fri, Nov 6
WestJet Logo
7:50 am - 1:35 pm
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 pm - 11:55 pm
ORD
-
YWG
9h 35m
1 stop
$378WestJet
Sat, Oct 31 - Fri, Nov 6
WestJet Logo
7:50 am - 1:35 pm
YWG
-
ORD
29h 45m
1 stop
WestJet Logo
2:20 pm - 11:55 pm
ORD
-
YWG
9h 35m
1 stop
$379WestJet
Thu, Sep 3 - Fri, Sep 18
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
$380WestJet
Sat, Jul 11 - Sun, Jul 12
Multiple Airlines Logo
4:15 pm - 9:00 am
YWG
-
ORD
16h 45m
2 stops
Multiple Airlines Logo
8:40 pm - 11:19 am
ORD
-
YWG
14h 39m
1 stop
$386Multiple Airlines
Thu, Jul 16 - Sun, Jul 19
Multiple Airlines Logo
9:20 am - 8:29 pm
YWG
-
ORD
11h 09m
1 stop
Multiple Airlines Logo
5:35 pm - 10:00 am
ORD
-
YWG
16h 25m
1 stop
$388Multiple Airlines
Booking Insights

KAYAK's insights & trends for Winnipeg to O'Hare Intl flights

Get data-powered insights and trends into flights from Winnipeg to O'Hare Intl 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 O'Hare Intl Airport?

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 O'Hare Intl Airport departing in October.

What’s the cheapest day of the week to fly from Winnipeg to Chicago O'Hare Airport?

The average price of all round-trip flights from Winnipeg to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

When flying from Winnipeg to Chicago O'Hare Airport, you should consider leaving on a Saturday and avoid Sundays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

What is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is September, where tickets cost $361 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is $881 and $692 respectively.

Can I save money by flying with a layover from Winnipeg to Chicago O'Hare Intl Airport?

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.

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Expert advice

Expert advice for your flight from Winnipeg to O'Hare Intl

 
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 seasonFebruary
Cheapest flight$178
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Winnipeg to Chicago O'Hare Airport

When to book flights from Winnipeg to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Winnipeg to O'Hare Intl 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 Winnipeg to Chicago O'Hare Airport flights

  • What is the cheapest flight from Winnipeg to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Winnipeg to Chicago O'Hare Intl Airport was $178 for a one-way ticket and $335 for a round-trip.

  • Do I need a passport to fly between Winnipeg and Chicago O'Hare Airport?

    Yes

  • Which airports will I be using when flying from Winnipeg to Chicago O'Hare Airport?

    Winnipeg airport is called Winnipeg and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Winnipeg to Chicago O'Hare Airport?

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

  • Which aircraft models fly most regularly from Winnipeg to Chicago O'Hare Airport?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Winnipeg to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Winnipeg to Chicago O'Hare Airport?

    Star Alliance is the only airline alliance operating flights between Winnipeg and Chicago O'Hare Airport.

  • On which days can I fly direct from Winnipeg to Chicago O'Hare Airport?

    There are nonstop flights from Winnipeg to Chicago O'Hare Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Winnipeg to Chicago O'Hare Airport?

    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 O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport with an airline and back to Winnipeg with another airline. Booking your flights between Winnipeg and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Chicago O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Intl Airport

  • 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 O'Hare Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Winnipeg to Chicago O'Hare Intl.
Find which airlines fly direct from Winnipeg Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Winnipeg to Chicago O'Hare Intl

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 O'Hare Intl 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 O'Hare Intl

 
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 O'Hare Intl? 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 9831 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

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

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

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.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Everything you need to know for your flight from Winnipeg to O'Hare Intl

Information on your arrival and departure airports

Winnipeg (YWG)
O'Hare Intl (ORD)