ORD - YWG

C$ 142 Find Cheap Flights from Chicago to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 13/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, 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 Chicago to Winnipeg, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to Winnipeg (ORD-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Winnipeg 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.

Recent round-trip flight deals from Chicago to Winnipeg

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Winnipeg.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
5:48 p.m. - 4:28 p.m.ORD-YWG
22h 40m1 stop
 Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 307
Find Deal
Tue, 6 May - Fri, 9 May
 Logo
5:10 a.m. - 4:28 p.m.ORD-YWG
11h 18m1 stop
 Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 335
Find Deal
Fri, 30 May - Mon, 2 Jun
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 431WestJet
Find Deal
Sun, 21 Sep - Thu, 25 Sep
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
C$ 469WestJet
Find Deal
Thu, 16 Oct - Fri, 24 Oct
Delta Logo
11:05 a.m. - 11:25 p.m.ORD-YWG
12h 20m2 stops
Delta Logo
6:40 a.m. - 4:30 p.m.YWG-ORD
9h 50m2 stops
C$ 500Delta
Find Deal
Wed, 28 May - Wed, 4 Jun
Delta Logo
7:05 a.m. - 11:25 p.m.ORD-YWG
16h 20m2 stops
Delta Logo
6:40 a.m. - 6:37 p.m.YWG-ORD
11h 57m2 stops
C$ 536Delta
Find Deal
Sat, 31 May - Tue, 3 Jun
Air Canada Logo
1:02 p.m. - 3:31 p.m.ORD-YWG
2h 29mdirect
Air Canada Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 610Air Canada
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Air Canada Logo
3:50 p.m. - 11:23 p.m.ORD-YWG
7h 33m1 stop
Air Canada Logo
5:00 a.m. - 12:54 p.m.YWG-ORD
7h 54m1 stop
C$ 618Air Canada
Find Deal
Fri, 20 Jun - Sun, 22 Jun
United Airlines Logo
10:00 a.m. - 5:38 p.m.ORD-YWG
7h 38m1 stop
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 722United Airlines
Find Deal
Thu, 17 Jul - Sun, 20 Jul
United Airlines Logo
7:58 p.m. - 10:33 p.m.ORD-YWG
2h 35mdirect
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 729United Airlines
Find Deal
Thu, 24 Jul - Mon, 11 Aug

Expert advice for your flight from Chicago to Winnipeg

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are specific to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to 15 cm more legroom than standard economy seats.


United's Priority Boarding places you in Zone 2, avoiding overhead bin space issues.

Air Canada

Air Canada's Preferred Economy seats offer up to 10 extra cm of legroom.


Air Canada offers priority check-in for higher fare classes and elite status travelers.

Read more about Air Canadaby Stefanie Waldek
Airports
ORD

For a quick security check, avoid peak times at ORD as lines can exceed 30 minutes. Off-peak hours are much faster.

Read more about ORDby Stefanie Waldek
YWG

Use the ArriveCAN app to fill out your customs declaration in advance at YWG, saving time at the electronic kiosk.

Read more about YWGby Mark Stachiew
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Air Canada and ORD

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
Mark Stachiew

Mark Stachiew

Expert on YWG

Mark Stachiew

Mark Stachiew

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

KAYAK's insights & trends for Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Winnipeg clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Winnipeg on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Winnipeg, 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 Chicago O'Hare Intl Airport to Winnipeg is April, where tickets cost C$ 362 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is C$ 962 and C$ 897 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Winnipeg?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Winnipeg, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Winnipeg, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

January

High season

July

Cheapest flight

C$ 142
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly (28% more expensive on average)
Flight from Chicago to Winnipeg

When to book flights from Chicago to Winnipeg

Are your dates flexible? Find out the best times to travel from Chicago to Winnipeg 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 Chicago to Winnipeg flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 103 for a one-way ticket and C$ 222 for a round-trip.

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

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

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

  • Which aircraft models fly most regularly from Chicago to Winnipeg?

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

  • Which airline alliances offer flights from Chicago to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

  • On which days can I fly direct from Chicago to Winnipeg?

    There are direct flights from Chicago to Winnipeg on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Winnipeg?

    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 Chicago to Winnipeg.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago 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 Chicago to Winnipeg?

    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 Winnipeg with an airline and back to Chicago with another airline.

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

    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 Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly direct from Chicago to Winnipeg?

Find which airlines fly direct from Chicago O'Hare Intl Airport to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Tuesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Wednesday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Saturday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Sunday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

See more nonstop flights

Direct returns

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Tuesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Wednesday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Thursday

Air Canada,Air New Zealand,Avianca, +1 more

Air Canada,Air New Zealand, +2 more

Friday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Saturday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

Sunday

Air Canada,Air New Zealand,Avianca, +2 more

Air Canada,Air New Zealand, +3 more

See more nonstop flights
See more nonstop flights

Top airline flying from Chicago to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. 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 Chicago to Winnipeg? 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.
7.0
Air CanadaOverall score based on 9192 reviews
6.3Food
7.0Comfort
7.3Boarding
6.8Entertainment
7.8Crew
Airline reviews

This flight didn't happen for me because of overbooking.

2.0 MediocreAnonymous, Apr 2025ORD - YOW
Read more Air Canada reviews

This flight didn't happen for me because of overbooking.

Poor air traffic controller staffing led to a 50%reduction on flights so we got to wait 4 hrs for our flight! Very disorganized at the gate Poor communication with customers

It was delayed by almost 90 minutes and that messed up our plans but it was beyond UA’s control that is what we heard

Terrible experience, flight was delayed both ways. Limited compensation for the 5+ hour delay. Will not be flying Air Canada Rouge, and don’t recommend you do either.

The boarding was relatively quick, the crew welcoming and flight uneventful. The omission of meals on all airlines is unacceptable especially when the flight is during a mealtime such as this one, (lunchtime), is unacceptable.

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

No Charging ports for personal electronics, which were required to use wifi entertainment.

Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)

They announced before boarding that the flight was full and there would be limited space in the overhead bins and you could check in for free. We did and after we boarded the plane found it was not full and there was plenty of space in the overhead bins. I’m not sure why they made this announcement.

Ok Did not like that the second leg of flight was moved earlier making it a rush to make

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

Information on your arrival and departure airports

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