YWG - ORD

$202 Find Cheap Flights from Winnipeg to Chicago O'Hare Airport - 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 O'Hare Intl departing on 9/10. 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

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Everything you should know

Cheapest round-trip
$362
Typical prices: $337-$772
Multiple Airlines
Sun 10/25Sun 11/1
YWG - ORD • 1 stop
Cheapest non-stop
$649
Typical prices: $352-$369
Air Canada
Fri 9/4Mon 9/7
YWG - ORD • Non-stop
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 2h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg $318 (round-trip)
Minneapolis (MSP)
Shortest trip • 4h 54m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 35% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sun, Oct 25 - Sun, Nov 1
Multiple Airlines Logo
6:55 pm - 11:05 am
YWG
-
ORD
16h 10m
1 stop
Multiple Airlines Logo
6:10 pm - 9:15 am
ORD
-
YWG
15h 05m
1 stop
$362Multiple Airlines
Tue, Sep 15 - Tue, Sep 22
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 11:10 am
ORD
-
YWG
17h 40m
1 stop
$372WestJet
Wed, Aug 26 - Sat, Aug 29
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
$383WestJet
Thu, Nov 12 - Tue, Nov 17
Multiple Airlines Logo
10:00 am - 11:05 am
YWG
-
ORD
25h 05m
1 stop
Multiple Airlines Logo
6:10 pm - 11:35 am
ORD
-
YWG
17h 25m
1 stop
$384Multiple Airlines
Thu, Oct 29 - Tue, Nov 3
Multiple Airlines Logo
8:05 pm - 5:30 pm
YWG
-
ORD
21h 25m
1 stop
Multiple Airlines Logo
6:10 pm - 9:15 am
ORD
-
YWG
15h 05m
1 stop
$384Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 11:10 am
ORD
-
YWG
17h 40m
1 stop
$386WestJet
Tue, Oct 6 - Thu, Oct 15
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
$386WestJet
Thu, Nov 12 - Tue, Nov 17
Multiple Airlines Logo
11:35 am - 11:05 am
YWG
-
ORD
23h 30m
2 stops
Multiple Airlines Logo
6:10 pm - 11:35 am
ORD
-
YWG
17h 25m
1 stop
$386Multiple Airlines
Sat, Aug 29 - Mon, Sep 7
United Airlines Logo
5:00 am - 8:28 pm
YWG
-
ORD
15h 28m
2 stops
United Airlines Logo
9:00 am - 11:20 pm
ORD
-
YWG
14h 20m
2 stops
$665United Airlines
Fri, Aug 28 - Sun, Aug 30
United Airlines Logo
2:00 pm - 4:35 pm
YWG
-
ORD
2h 35mnonstop
United Airlines Logo
9:15 am - 11:52 am
ORD
-
YWG
2h 37mnonstop
$682United 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.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from Winnipeg usually cost between $369 and $574 in October.
The lowest price found in the past 5 days was $362 on Multiple Airlines (Oct 25-Nov 1).

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 Tuesdays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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 $369 (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 $657, 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 season

February

Cheapest flight

$202
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 6% 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 $202 for a one-way ticket and $362 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 $389 or less one-way and $545 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

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)