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CHI - YWG

Find cheap flights from Chicago to Winnipeg from $158

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 4/10. 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
0 bags
Thu 4/18
Thu 4/25

Search 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
In the last 7 days travelers have searched 47,600,107 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Winnipeg

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.
9:34 pm - 4:05 pmORD-YWG
18h 31m1 stop
8:15 pm - 4:45 pmYWG-ORD
20h 30m2 stops
Tue, Apr 16 - Tue, Apr 23
9:34 pm - 4:05 pmORD-YWG
18h 31m1 stop
4:00 pm - 4:45 pmYWG-ORD
24h 45m3 stops
Tue, Apr 16 - Tue, Apr 23
5:00 pm - 11:23 pmMDW-YWG
6h 23m1 stop
6:55 am - 10:26 amYWG-MDW
3h 31m1 stop
$414Delta
Find Deal
Sat, Jun 1 - Sat, Jun 8
3:50 pm - 11:23 pmORD-YWG
7h 33m1 stop
6:55 am - 11:29 amYWG-ORD
4h 34m1 stop
$435Delta
Find Deal
Sat, Jun 1 - Sat, Jun 8
10:00 am - 2:55 pmMDW-YWG
28h 55m1 stop
5:00 am - 4:24 pmYWG-MDW
11h 24m2 stops
$453WestJet
Find Deal
Tue, Apr 16 - Tue, Apr 23
9:15 pm - 9:50 amORD-YWG
12h 35m1 stop
7:30 am - 2:54 pmYWG-ORD
7h 24m1 stop
$456Air Canada
Find Deal
Mon, Jun 10 - Tue, Jun 18
6:00 am - 5:55 pmORD-YWG
11h 55m1 stop
7:30 am - 2:54 pmYWG-ORD
7h 24m1 stop
$457Air Canada
Find Deal
Tue, May 7 - Wed, May 8
5:57 pm - 2:55 pmORD-YWG
20h 58m1 stop
5:35 pm - 9:58 pmYWG-ORD
4h 23m1 stop
$492WestJet
Find Deal
Tue, Apr 16 - Tue, Apr 23
1:03 pm - 3:29 pmORD-YWG
2h 26mnonstop
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
$878United Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 19
1:03 pm - 3:29 pmORD-YWG
2h 26mnonstop
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
$973United Airlines
Find Deal
Thu, Jun 6 - Sun, Jun 9

Flights from Chicago to Winnipeg - Travel Insights & Trends

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 is the cheapest Chicago to Winnipeg flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Winnipeg.
Our data shows that the cheapest route for a one-way flight from Chicago to Winnipeg cost $338 and was between Chicago O'Hare Intl Airport and Winnipeg. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $235.

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

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

What is the cheapest month to fly from Chicago to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago 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 to Winnipeg is May, where tickets cost $381 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is $897 and $737 respectively.

How far in advance should I book a flight from Chicago to Winnipeg?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Winnipeg, 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 Chicago to Winnipeg, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

Which airlines provide the cheapest flights from Chicago to Winnipeg?

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 Chicago to Winnipeg found on KAYAK was with WestJet for $210. Delta proposed a round-trip connection from $414 and WestJet from $453.

Which cabin class options are there for flights between Chicago and Winnipeg?

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 Chicago to Winnipeg take?

This flight route requires at least one stop and takes a minimum of 2h 26m.

Good to know

Low season

January

High season

June

Cheapest flight

$158
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Airport 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 flights from Chicago to Winnipeg

  • What is the cheapest flight from Chicago to Winnipeg?

    In the last 3 days, the lowest price for a flight from Chicago to Winnipeg was $158 for a one-way ticket and $343 for a round-trip.

  • Do I need a passport to fly between Chicago and Winnipeg?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Winnipeg.

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

    On your way to Winnipeg, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Winnipeg, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Winnipeg are Delta and WestJet. With an average price for the route of $612 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 $488 and an overall rating of 7.5.

  • 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 travelers 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

Top tips for finding a cheap flight from Chicago to Winnipeg

  • Looking for a cheap flight? 25% of our users found flights on this route for $797 or less round-trip.

Prefer to fly non-stop from Chicago to Winnipeg?

Find which airlines fly direct from Chicago to Winnipeg, which days they fly and book direct flights.

Nonstop departures

Chicago 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 direct flights

Nonstop returns

Winnipeg to Chicago

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 direct flights
See more direct flights

Top 4 airlines serving from Chicago to Winnipeg

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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
81entertainment
86crew
81overall
79comfort
75food
82boarding
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

It wasn't really their fault it was the horrible winds and we just got unlucky.

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

I like WJ but I don’t like traveling anymore

We requested 2 wheel chairs upon arrival. On board an attendant told us to remain in our seats until everyone was off the plane. we were in row 11 and thought we would be off early. After all were off, a different attendant said we should leave, and that the chairs were gone. One was available for my friend who had just spent 9 days in hospital but I had to walk quite some distance. Eventually a cart arrived to take us the rest of the way. This was over an hour after our arrival. The staff at the terminal did their best to help us but if we had been allowed off with the other passengers, our ride home would have been an hour earlier.

Our flight experience was great! Flight staff was funny and offered great service. Made record flying time coming home from Vegas after having to wait for planes on the tarmac because of high winds

Seats can use more cushioning, it felt very hard. The snack option could be better

Over all good. I had some issues with trying to buy my seat. The Westjet system kept trying to charge my credit card, without getting the seat. In the end after 5 times being charged, I got my seat.

I did not have a meal or entertainment, but flight was comfortable, beverage service was quick, crew was very helpful and pleasant. And a very smooth flight overall.

Flight was on time! Downloaded the entertainment app in advance - worked well

I liked when we actually were allowed to get on the airplane back to Edmonton… What could’ve been better well, not having our flight be delayed five hours could’ve been better… And then canceling our flight from Edmonton to Toronto, and then rescheduling us to fly from Honolulu to Edmonton -Edmonton to Vancouver, and then Vancouver to Toronto with a 12 hour layover in Edmonton pretty much was hell… Total travel time to get home 38 hours that’s really what could’ve been better. The two gate attendants for WestJet in Honolulu told us to come back to the gate to try to make other arrangements because they had to board the Calgary flight 1st and they didn’t have time to talk to me but by the time I came back when they told us to they said you should’ve come earlier to make these arrangements everyone else already changed their flights… We found out later that 30 people did not get on the 2:30 AM Edmonton flight. They ended up getting on the midnight flight to Calgary and making other arrangements to Toronto and so forth which we could’ve taken advantage of that if they had allowed us to when I initially had went up and approached the two gate attendance one of their names was Denise. One of the kindest WestJet employee was the one who received us in Edmonton, who felt so bad about the entire situation she got us for more meal vouchers and flew us first class from Vancouver to Toronto. In Honolulu they had given us two vouchers to use for dinner and they weren’t valid outside of Canada so we had purchased a meal and they were completely useless… But nowhere did it say that they could only be used in Canada So when we received more food vouchers in Edmonton, all of them did end up working in Canada, but it was just so convoluted. Overall, we have traveled to other countries even going as far as Africa… and that experience was far easier than flying to Hawaii from Canada I cannot believe any of this happened and how inconvenient it was We arrived, exhausted after 38 hours of travel, and could not even go to work on Monday. I look forward to hearing from KAYAK or from WestJet for some sort of compensation over the situation.

Delta gave out earbuds for in-flight entertainment, which was nice. But the legroom seems to decrease every year.

Flight late …60 minutes No food No wifi No entertainment system A disaster!!!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

All good, useful to have the united app from check in to boarding

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Flight delayed two and a half hours from Toronto to Calgary Philadelphia to Toronto we were listed as standbys !!! Very concerning

Flight delayed at the last moment Hill next day and havé to drag at Hotel at our cost and bec day was again delayed 4 Times because no crée and no pilot

The flight was more compact. The flight was more turbulent than usual. Otherwise no complaints.

No food, not even snacks on the 6hr flight from Newark to Vancouver! The movie collection made up for it though and they did come around with drinks twice. Just good to know so you can eat ahead/bring snacks onto the flight. It was a bumpy ride induced by wind and rain but otherwise got to the destination safely and promptly.

On the flight back from SFO to Vancouver ..the crew was less than professional. They completely missed asking if I wanted a drink (and I was awake at all times) and I had to walk to the back of the plane to ask for a cup of water to take with my medication. Also, there was a charge for ear adapters for the movie screen which were given out free on the flight from Vancouver to SFO. The flight from Vancouver to SFO had pleasant crew members. What a difference in the flight back.

Announcements were to loud, too insistent and too often. The same messages can be made in a nice relaxed, yet efficient manner. There is no need to "talk down" as if on a mild power trip. It's immature and unnecessary. This is a constant irritant especially with Air Canada. Learn from your European competitors to have a bit of class.

New Airbus 220 with all the amenities. Not sure why hot beverages were not served as flight turned out to be very smooth…

My flight was cancelled. The flight they booked me on was delayed over 2 hours with mechanical problems so I missed my connection and they ran out of hotel rooms, so I had to book and pay for it on my own. I also had to pay for food out of pocket. It was a terrible experience.

Flight delayed by 3 hours because of lack of available plane. So why were we notified on the morning of our departure? Is your scheduling that bad? We, in zone 4, were told to check in our 2 carry-ons because of lack of storage space in the plane. When we boarded the luggage spaces directly above us were empty and so were others. In fact there were many empty seats. If each passenger is allowed one carry-on why is that right revoked at the last minute at air Canada's whim? The AC app doesn't work. It refused to show our boarding passes, and track our luggage. In fact it indicated that the flight was on time even though it was delayed by over 3 1/2 hours

The cabin crew were really good!! Check in etc. was very good. We enjoyed the aisle seats as the plane was small! Couldn’t comment on the food as we didn’t order anything!

Book cheap flights from Chicago to Winnipeg

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Winnipeg found on KAYAK in the last 72 hours.
4/10Wed
1 stop
12h 14mORD-YWG
$158
5/14Tue
1 stop
19h 09mMDW-YWG
$162
5/14Tue
1 stop
18h 00mORD-YWG
$176
5/1Wed
2 stopsWestJet
12h 46mORD-YWG
$210
5/14Tue
2 stopsWestJet
14h 59mMDW-YWG
$218
7/26Fri
1 stopDelta
7h 31mORD-YWG
$256
4/27Sat
1 stopPorter Airlines
13h 19mMDW-YWG
$259
5/5Sun
1 stopDelta
16h 55mMDW-YWG
$357
7/26Fri
nonstopAir Canada
2h 26mORD-YWG
$628
8/6Tue
nonstopAir Canada
2h 26mORD-YWG
$714

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Flights to Winnipeg

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

$235

Browse destinations: