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YWG - ORD

Find cheap flights from Winnipeg to Chicago from C$ 211

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 5/6. 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
0 bags
Fri 7/6
Fri 14/6

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Chicago.
In the last 7 days, travellers have searched 43,707,506 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:55 a.m. - 10:26 a.m.YWG-ORD
3h 31m1 stop
3:50 p.m. - 11:23 p.m.ORD-YWG
7h 33m1 stop
C$ 522Delta
Find Deal
Sat, 25 May - Wed, 29 May
9:35 a.m. - 9:03 p.m.YWG-ORD
11h 28m2 stops
6:05 a.m. - 11:35 a.m.ORD-YWG
5h 30m1 stop
C$ 523WestJet
Find Deal
Sat, 8 Jun - Tue, 11 Jun
6:55 a.m. - 11:44 a.m.YWG-ORD
4h 49m1 stop
3:55 p.m. - 11:29 p.m.ORD-YWG
7h 34m1 stop
C$ 526WestJet
Find Deal
Sat, 8 Jun - Tue, 11 Jun
8:00 a.m. - 11:32 a.m.YWG-ORD
27h 32m2 stops
12:32 p.m. - 12:44 a.m.ORD-YWG
12h 12m1 stop
C$ 529
Find Deal
Thu, 6 Jun - Thu, 13 Jun
5:35 p.m. - 10:39 p.m.YWG-ORD
5h 04m1 stop
6:07 a.m. - 11:23 p.m.ORD-YWG
17h 16m1 stop
C$ 533WestJet
Find Deal
Wed, 29 May - Sun, 2 Jun
6:55 a.m. - 11:43 a.m.YWG-ORD
4h 48m1 stop
6:00 a.m. - 11:36 a.m.ORD-YWG
5h 36m1 stop
C$ 542Delta
Find Deal
Sat, 20 Jul - Thu, 25 Jul
2:18 p.m. - 4:46 p.m.YWG-ORD
2h 28mdirect
4:00 p.m. - 12:07 a.m.ORD-YWG
8h 07m1 stop
C$ 626Air Canada
Find Deal
Mon, 24 Jun - Sat, 29 Jun
2:18 p.m. - 4:46 p.m.YWG-ORD
2h 28mdirect
9:15 p.m. - 8:55 a.m.ORD-YWG
11h 40m1 stop
C$ 634Air Canada
Find Deal
Tue, 4 Jun - Sat, 8 Jun
2:18 p.m. - 4:46 p.m.YWG-ORD
2h 28mdirect
5:00 p.m. - 12:10 a.m.ORD-YWG
7h 10m1 stop
C$ 679United Airlines
Find Deal
Sat, 8 Jun - Tue, 11 Jun
2:18 p.m. - 4:46 p.m.YWG-ORD
2h 28mdirect
5:00 p.m. - 12:10 a.m.ORD-YWG
7h 10m1 stop
C$ 686United Airlines
Find Deal
Tue, 4 Jun - Tue, 11 Jun

Flights from Winnipeg to Chicago - Travel Insights & Trends

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.

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

The average price of all flights from Winnipeg to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Winnipeg to Chicago, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Thursday is the cheapest day to fly and Monday is the most expensive.

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 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 November, where tickets cost C$ 579 on average. On the other hand, the most expensive months are May and August, where the average cost of tickets is C$ 950 and C$ 823 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Winnipeg to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Winnipeg to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 41 days before departure.

Which airlines provide the cheapest flights from Winnipeg to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Winnipeg to Chicago found on KAYAK was with WestJet for C$ 305. Delta proposed a round-trip connection from C$ 522 and WestJet from C$ 523.

Which airlines fly direct between Winnipeg and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Winnipeg to Chicago O'Hare Intl Airport.
There is just one airline that flies from Winnipeg to Chicago O'Hare Intl Airport direct and that is United Airlines. The best one-way deal found from United Airlines for the route is C$ 607.

How many flights are there between Winnipeg and Chicago O'Hare Intl Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Winnipeg and lands in Chicago O'Hare Intl Airport, with an average flight time of 2h 28m. The most common departure time is 2:00 p.m. and most flights take off in the afternoon. Each week, there are 7 flights.

Which cabin class options are there for flights between Winnipeg and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Winnipeg to Chicago take?

Direct flights from Winnipeg generally make it to Chicago in 2h 28m. The flying distance between the two cities is 1,829 km.

What’s the earliest departure time from Winnipeg to Chicago?

Early birds can take the earliest flight from Winnipeg at 2:18 pm and will be landing in Chicago O'Hare Intl Airport at 4:46 pm.

What’s the latest departure time from Winnipeg to Chicago?

If you prefer to fly at night, the latest flight from Winnipeg to Chicago O'Hare Intl Airport jets off at 2:18 pm and lands at 4:46 pm.

Good to know

Low season

July

High season

May

Cheapest flight

C$ 211
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly (29% more expensive 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 3 days, the lowest price for a flight from Winnipeg to Chicago O'Hare Intl Airport was C$ 154 for a one-way ticket and C$ 381 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 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, Delta or WestJet?

    The two airlines most popular with KAYAK users for flights from Winnipeg to Chicago are Delta and WestJet. With an average price for the route of C$ 665 and an overall rating of 8.0, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 951 and an overall rating of 7.5.

  • 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.

See more FAQs

Top tips for finding a cheap flight from Winnipeg to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 267 or less one-way and C$ 669 or less round-trip.

Prefer to fly non-stop from Winnipeg to Chicago?

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

Nonstop departures

Winnipeg to Chicago O'Hare Intl

Monday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Tuesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Wednesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Thursday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Friday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Saturday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Sunday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

See more nonstop flights

Nonstop returns

Chicago O'Hare Intl to Winnipeg

Monday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Tuesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Wednesday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Thursday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Friday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Saturday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

Sunday

Air Canada, Air New Zealand, United Airlines

Air Canada, Air New Zealand, +1 more

See more nonstop flights
See more nonstop flights

Top 5 airlines serving from Winnipeg to Chicago

 
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 Chicago? 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.
8.1
WestJet EncoreOverall score based on 52 reviews
7.5Entertainment
7.6Comfort
7.4Food
8.6Boarding
8.7Crew
Airline reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

10.0 ExcellentDarren, May 2023YYZ - LAX
Read more about WestJet Encore reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

Pros: "Friendly staff and the support they offered to my mother who needed a wheelchair."
Cons: "I would have liked to have had WestJet internet and entertainment access. It was not offered on our flight from Toronto to Fredericton."
Pros: "The fact that military personnel and retired military personnel and their spouse can check in luggage for free. The check in crew was also very courteous."
Pros: "It ran on time. The pilot landed the plane without a big jolt. We could board and deplane using 2 exits."
Cons: "Seat space"
Pros: "Rotten stuff cancels out the good doesn't it. Be great if you could take some courses from Stephen Covey as you are missing some skills sets in hospitality. And stop being so cheap with the 3rd rate old old movies!"
Cons: "I did not appreciate having the second row to the last on my 2nd plane coming back - I only had a turn around time of 20 minutes to catch my third Westjet flight. When we asked if the plane would wait for us - your crew just laughed in our faces."
Pros: "Great, friendly crew in this scenic trip across to Victoria. Nice new aircraft operating this route."
Pros: "Cheerfulness of WestJet employees."
Cons: "Seat comfort; seats hard. Person next to me average size but still spilled into my seat with “man-spreading” and shoulders."
Pros: "Efficient crew and reasonable seating"
Cons: "Need more legroom or a device to fold passenger legs for the flight duration..."
Pros: "Crew was good. Seats need to be updated and are confining. I appreciated being able to disembark through front and rear door."
Cons: "More space between the seats."
Pros: "the crew was very polite but the flight was too short to have a meal"
Cons: "delayed embarking"

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Westjet delayed then rebooked us on flights for economy class when we paid for business class and now need a refund for fare difference and they aren't getting back to us

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

Book cheap flights from Winnipeg to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Winnipeg to Chicago found on KAYAK in the last 72 hours.
5/6Wed
1 stop
12h 47mYWG-ORD
C$ 211
5/6Wed
2 stops
15h 45mYWG-ORD
C$ 238
26/8Mon
1 stopWestJet
8h 27mYWG-ORD
C$ 305
14/7Sun
1 stopDelta
8h 12mYWG-ORD
C$ 310
30/7Tue
1 stopWestJet
4h 29mYWG-ORD
C$ 359
14/7Sun
1 stopDelta
8h 12mYWG-ORD
C$ 362
5/6Wed
directUnited Airlines
2h 28mYWG-ORD
C$ 560
8/7Mon
directAir Canada
2h 28mYWG-ORD
C$ 785
26/8Mon
directAir Canada
2h 32mYWG-ORD
C$ 842
14/7Sun
directUnited Airlines
2h 28mYWG-ORD
C$ 974

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Winnipeg - Chicago Flights

Departure:

Winnipeg (undefined)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Winnipeg

Cabin classes:

C$ 11,494
C$ 2,688
C$ 4,500
C$ 497