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CHI - YWG

$219 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 8/2. 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
Sun 6/9
Sun 6/16

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 43,895,468 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap flight deals from Chicago to Winnipeg (CHI-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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:00 am - 7:45 pmORD-YWG
12h 45m2 stops
8:00 am - 4:39 pmYWG-ORD
8h 39m1 stop
Thu, Jul 18 - Wed, Jul 24
6:07 am - 4:45 pmORD-YWG
10h 38m1 stop
8:30 am - 5:05 pmYWG-ORD
8h 35m1 stop
$390WestJet
Find Deal
Sun, May 12 - Sat, May 25
9:46 am - 11:23 pmMDW-YWG
13h 37m1 stop
8:00 am - 9:46 pmYWG-MDW
13h 46m1 stop
$410WestJet
Find Deal
Tue, Jun 4 - Wed, Jun 12
2:24 pm - 11:29 pmMDW-YWG
9h 05m1 stop
6:55 am - 5:04 pmYWG-MDW
10h 09m2 stops
$411Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
9:46 am - 10:40 pmMDW-YWG
12h 54m2 stops
8:00 am - 5:59 pmYWG-MDW
9h 59m1 stop
$415WestJet
Find Deal
Tue, Jun 4 - Wed, Jun 12
1:24 pm - 11:29 pmMDW-YWG
10h 05m2 stops
6:55 am - 5:04 pmYWG-MDW
10h 09m2 stops
$416Delta
Find Deal
Tue, Jun 11 - Thu, Jun 13
2:15 pm - 8:57 pmORD-YWG
6h 42m1 stop
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
$456United Airlines
Find Deal
Tue, Jun 18 - Wed, Jun 19
2:15 pm - 8:57 pmORD-YWG
6h 42m1 stop
4:18 pm - 11:59 pmYWG-ORD
7h 41m1 stop
$471United Airlines
Find Deal
Tue, Jun 18 - Wed, Jun 19
9:15 pm - 8:52 amORD-YWG
11h 37m1 stop
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
$479Air Canada
Find Deal
Fri, Jun 21 - Tue, Jun 25
9:15 pm - 8:52 amORD-YWG
11h 37m1 stop
2:18 pm - 4:46 pmYWG-ORD
2h 28mnonstop
$587Air Canada
Find Deal
Mon, Jun 17 - Fri, Jun 21

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 $436 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 $743.

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 Friday, as it's usually the priciest day. When flying back from Winnipeg, Wednesday 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 March, where tickets cost $298 on average. On the other hand, the most expensive months are July and December, where the average cost of tickets is $981 and $728 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 28 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 Delta for $219. WestJet proposed a round-trip connection from $390 and Delta from $411.

Which airlines fly non-stop between Chicago and Winnipeg?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Winnipeg.
There is just one airline that flies from Chicago to Winnipeg direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $413.

How many flights are there between Chicago and Winnipeg per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Winnipeg, with an average flight time of 2h 26m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

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?

The duration of a nonstop flight to Winnipeg from Chicago is typically 2h 24m. The journey crosses a distance of 720 miles.

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

Early birds can take the earliest flight from Chicago at 1:03 pm and will be landing in Winnipeg at 3:29 pm.

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

If you prefer to fly at night, the latest flight from Chicago to Winnipeg jets off at 1:03 pm and lands at 3:29 pm.

Good to know

Low season

January

High season

February

Cheapest flight

$219
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 $219 for a one-way ticket and $346 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?

    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 nonstop flights from Chicago to Winnipeg on a daily basis.

  • 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 $596 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 $558 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 $870 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

 
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.
8.0
DeltaOverall score based on 10778 reviews
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

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!

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.

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

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.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Too many oversized carryon baggage. If carrier reduced checked luggage fee this could be avoided. The staff were friendly and helpful, very professional.

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

food worker strike caused lack of service. I know, not your fault but a bit of a inconvenience.

The staff on the WestJet flight were friendly and helpful. The flight was smooth and we arrived 30 minutes ahead of time.

The on time performance and the ease of boarding are great. The crew were cordial. During landing the pilot made a hard landing with some swerve that was a bit rough but other than that everything else is as smooth as it can be.

Horrible, flight on the way to Vegas was delayed significantly and then on my way back my second flight was cancelled

If they have a tv for movie or map during 5h flight could be better and the food can purchase on flight are ok with that.

Crew was rude.didn’t even say hi or welcome to board

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.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

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.

Flew SEA-CA, then CA-NRT. First flight was short but very uncomfortable, dirty, and had very small overhead storage space. The seats and fans were not cleaned and had visible dirt on them. Second flight was perfect.

My second flight ended up being through United and it was fine. Again, just frustrating that it was so late.

Everything went smoothly and as expected. We were on time and one flight arrived early.

First time flying Air Canada and the trip was very pleasant! They did a great job getting us out of Toronto and into Rome (early!) For an international flight it was very enjoyable.

This is not a Business Class equipped airplane and even the crew apologize before take over BUT BUT Air Canada charged full business class fare

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.

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.
8/2Fri
1 stopDelta
7h 28mORD-YWG
$219
5/12Sun
2 stopsWestJet
16h 48mORD-YWG
$232
8/2Fri
2 stopsWestJet
13h 00mORD-YWG
$242
8/1Thu
1 stopDelta
9h 22mORD-YWG
$251
5/12Sun
1 stopWestJet
10h 38mORD-YWG
$267
5/12Sun
3 stops
37h 35mORD-YWG
$335
8/1Thu
nonstopUnited Airlines
2h 26mORD-YWG
$825

Search by stops

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Last minute flights from Chicago to Winnipeg

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Winnipeg that are departing in the next 10 days.
5/12Sun
multi-stopWestJet
6h 59mMDW-YWG
5/25Sat
multi-stopWestJet
8h 43mYWG-MDW
$518
5/12Sun
multi-stopWestJet
11h 51mMDW-YWG
5/25Sat
multi-stopWestJet
8h 43mYWG-MDW
$814
5/14Tue
multi-stopWestJet
12h 27mMDW-YWG
5/17Fri
multi-stopWestJet
14h 21mYWG-MDW
$849
5/14Tue
multi-stopWestJet
12h 27mMDW-YWG
5/17Fri
multi-stopWestJet
5h 45mYWG-MDW
$859
5/14Tue
multi-stopWestJet
6h 59mMDW-YWG
5/17Fri
multi-stopWestJet
5h 45mYWG-MDW
$983
5/12Sun
multi-stopWestJet
6h 59mMDW-YWG
5/25Sat
multi-stopWestJet
4h 07mYWG-MDW
$1,030
5/10Fri
multi-stop
8h 25mMDW-YWG
5/11Sat
multi-stop
8h 43mYWG-MDW
$1,274
5/10Fri
multi-stopWestJet
6h 59mMDW-YWG
5/11Sat
multi-stopWestJet
10h 00mYWG-MDW
$1,310
5/10Fri
multi-stopWestJet
12h 56mMDW-YWG
5/11Sat
multi-stopWestJet
10h 25mYWG-MDW
$1,320

Search by stops

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Flights to Winnipeg

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

$1,302
$743

Browse destinations: