ORD - YWG

C$ 231 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 5/7. 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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Expert advice
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Flights Deals

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.
WestJet Logo
5:30 p.m. - 9:03 a.m.ORD-YWG
15h 33m1 stop
WestJet Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 403WestJet
Find Deal
Thu, 15 May - Sun, 18 May
 Logo
5:01 a.m. - 4:28 p.m.ORD-YWG
11h 27m1 stop
 Logo
9:00 a.m. - 2:48 p.m.YWG-ORD
5h 48m1 stop
C$ 411
Find Deal
Wed, 25 Jun - Mon, 30 Jun
 Logo
5:01 a.m. - 4:28 p.m.ORD-YWG
11h 27m1 stop
 Logo
8:30 a.m. - 4:44 p.m.YWG-ORD
8h 14m1 stop
C$ 415
Find Deal
Thu, 5 Jun - Mon, 9 Jun
 Logo
5:40 a.m. - 8:16 p.m.ORD-YWG
14h 36m2 stops
 Logo
9:00 a.m. - 5:11 p.m.YWG-ORD
8h 11m1 stop
C$ 436
Find Deal
Thu, 14 Aug - Mon, 18 Aug
Air Canada Logo
7:58 p.m. - 10:33 p.m.ORD-YWG
2h 35mdirect
Air Canada Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
C$ 664Air Canada
Find Deal
Sun, 15 Jun - Mon, 16 Jun
Air Canada Logo
7:58 p.m. - 10:33 p.m.ORD-YWG
2h 35mdirect
Air Canada Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 666Air Canada
Find Deal
Fri, 13 Jun - Fri, 20 Jun
Delta Logo
7:10 a.m. - 4:45 p.m.ORD-YWG
9h 35m2 stops
Delta Logo
6:45 a.m. - 12:55 p.m.YWG-ORD
6h 10m2 stops
C$ 706Delta
Find Deal
Sat, 31 May - Tue, 10 Jun
Delta Logo
11:07 a.m. - 11:25 p.m.ORD-YWG
12h 18m2 stops
Delta Logo
5:35 p.m. - 9:30 p.m.YWG-ORD
3h 55m1 stop
C$ 736Delta
Find Deal
Wed, 28 May - Thu, 5 Jun
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$ 765United Airlines
Find Deal
Fri, 6 Jun - Mon, 9 Jun
United Airlines Logo
5:02 a.m. - 1:09 p.m.ORD-YWG
8h 07m1 stop
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
C$ 779United Airlines
Find Deal
Fri, 6 Jun - Mon, 9 Jun
Expert advice

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
Useful Info

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$ 363 (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$ 963 and C$ 898 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 seasonJanuary
High seasonJuly
Cheapest flightC$ 231
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$ 167 for a one-way ticket and C$ 291 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.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 755 or less round-trip.

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 9245 reviews
7.8Crew
6.8Entertainment
7.0Comfort
7.3Boarding
6.3Food
Airline reviews

All was good except for the seats, not very comfy.

8.0 ExcellentAnonymous, Apr 2025ORD - YVR
Read more Air Canada reviews

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

I hope these comments will find their way to AC customer experience team. Me and my spouse 50 years of aged coming back from 7 days perfect vacation... While boarding in FLL flight AC1621, one of the boarding agents (tall aged african american) man literelly yeld at my wife during the picture talking process. MAM ! STEP !! BACK !!! We are not illegal immegrants beying deported, nor are we in the millitary. We are customers returning home. This was unacceptable. While boarding in YYZ flight AC1154, one of the boarding agents (tall aged caucasian) man criticied with several complesant remarks my passport condition saying that I could not travel intl with it due to stain, decoloration, and BLOOD. My passport does not have blood on it! Yes it might be in less than perfect condition, but their are ways to talk to customer that does not imply not allow a boarding agent to be angry fathery like, or a custom agent looking at a suspicious individual. Both experience were less than acceptable for might I remind you a paying CUSTOMER returning home.

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

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.

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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