YWG - ORD

C$ 258 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 21/9. 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
C$ 359
Typical prices: C$ 467-C$ 549
WestJet
Fri 18/9Mon 21/9
YWG - ORD • 1 stop
Cheapest direct flights
C$ 864
Typical prices: C$ 1,227-C$ 1,864
Air Canada
Tue 13/10Sun 18/10
YWG - ORD • Direct
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Priority Boarding helps secure bin space; Air Canada priority is elite-only.
United Wi-Fi varies; Air Canada offers free messaging for Aeroplan members.
Expert advice
Expert advice
Expert advice
Expert advice
Direct 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 C$ 418 (round-trip)
Minneapolis (MSP)
Shortest trip • 3h 39m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 41% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals

Cheap Flights from Winnipeg to Chicago (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 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, 18 Sep - Mon, 21 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
C$ 359WestJet
Fri, 18 Sep - Mon, 21 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 2:40 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
21h 10m2 stops Calgary Vancouver Intl
C$ 469WestJet
Thu, 10 Sep - Sun, 13 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 p.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
C$ 489WestJet
Fri, 16 Oct - Thu, 22 Oct
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
7:45 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 10m2 stops Fort Lauderdale Toronto Pearson Intl
C$ 513Multiple Airlines
Sun, 18 Oct - Thu, 22 Oct
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
7:45 a.m. - 12:55 a.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
17h 10m2 stops Fort Lauderdale Toronto Pearson Intl
C$ 514Multiple Airlines
Tue, 22 Sep - Tue, 29 Sep
Multiple Airlines Logo
6:05 p.m. - 9:00 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
14h 55m1 stop Toronto Pearson Intl
Multiple Airlines Logo
9:55 a.m. - 7:49 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
9h 54m1 stop Toronto Pearson Intl
C$ 515Multiple Airlines
Sat, 12 Sep - Tue, 15 Sep
Air Canada Logo
12:20 p.m. - 7:48 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
7h 28m1 stop Toronto Pearson Intl
Air Canada Logo
9:55 a.m. - 4:27 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
6h 32m1 stop Toronto Pearson Intl
C$ 691Air Canada
Wed, 23 Sep - Fri, 25 Sep
Air Canada Logo
5:00 a.m. - 11:21 a.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
6h 21m1 stop Toronto Pearson Intl
Air Canada Logo
9:50 a.m. - 4:27 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
6h 37m1 stop Toronto Pearson Intl
C$ 697Air Canada
Wed, 23 Sep - Fri, 25 Sep
United Airlines Logo
5:00 a.m. - 9:59 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
16h 59m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
9:25 p.m. - 4:27 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
19h 02m2 stops Nashville Intl Toronto Pearson Intl
C$ 861United Airlines
Wed, 23 Sep - Fri, 25 Sep
United Airlines Logo
5:00 a.m. - 9:59 p.m.YWG  Winnipeg-ORD Chicago O'Hare Intl
16h 59m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
9:25 p.m. - 4:27 p.m.ORD  Chicago O'Hare Intl-YWG Winnipeg
19h 02m2 stops Nashville Intl Toronto Pearson Intl
C$ 907United Airlines
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 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 September.

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from Winnipeg usually cost between C$ 709 and C$ 964 in September.
The lowest price found in the past 5 days was C$ 359 on WestJet (18 Sep–21 Sep).

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 C$ 492 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is C$ 1,227 and C$ 964 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 C$ 908, prices are generally cheapest when you fly direct.

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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 United Airlines, Air Canada and ORD

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
Mark Stachiew

Mark Stachiew

Expert on YWG

Mark Stachiew has been exploring the world and writing about it for more than 30 years. His travel stories have appeared in numerous newspapers, magazines and online publications in Canada, the United States and beyond.

Read more

Good to know

Low season

February

Cheapest flight

C$ 258
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly and prices are also 10% lower on average.
Flight from Winnipeg to Chicago

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 Winnipeg to Chicago 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 C$ 258 for a one-way ticket and C$ 359 for a round-trip.

  • Which airports will I be using when flying from Winnipeg to Chicago?

    On your way to Chicago, you’ll fly out from Winnipeg. You’ll be landing at 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 direct flights from Winnipeg to Chicago on a daily basis.

  • Which is the best airline for flights from Winnipeg to Chicago, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Chicago are United Airlines and WestJet. With an average price for the route of C$ 957 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 488 and an overall rating of 7.2.

  • 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 travellers 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 O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 614 or less one-way and C$ 709 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 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 nonstop 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 nonstop flights

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

Information on your arrival and departure airports

Winnipeg (YWG)
O'Hare Intl (ORD)