Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

CHI - YWG

$148 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 6/22. 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
Sat 6/29
Sat 7/6

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 42,686,544 times on KAYAK, and here is why:

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

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Bundle and saveSave money when you bundle your flight + hotel.

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
5:15 pm - 11:29 pmORD-YWG
6h 14m1 stop
6:05 pm - 4:57 pmYWG-ORD
22h 52m1 stop
$380WestJet
Find Deal
Fri, Jun 21 - Tue, Jun 25
5:55 pm - 11:40 amORD-YWG
17h 45m1 stop
6:30 am - 7:06 pmYWG-ORD
12h 36m2 stops
Sun, Jun 23 - Tue, Jul 2
5:16 am - 1:21 pmORD-YWG
8h 05m1 stop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$456United Airlines
Find Deal
Sat, Jun 29 - Sun, Jun 30
8:00 am - 10:05 pmMDW-YWG
14h 05m1 stop
12:20 pm - 9:37 pmYWG-MDW
9h 17m2 stops
$472Porter Airlines
Find Deal
Fri, Jun 28 - Fri, Jul 5
11:00 am - 5:52 pmORD-YWG
6h 52m1 stop
8:15 am - 2:40 pmYWG-ORD
6h 25m1 stop
$499Air Canada
Find Deal
Sun, Jun 23 - Tue, Jul 2
10:55 am - 7:11 pmORD-YWG
8h 16m1 stop
11:50 am - 8:11 pmYWG-ORD
8h 21m1 stop
$504Air Canada
Find Deal
Tue, Jul 2 - Mon, Jul 29
7:10 am - 11:29 pmORD-YWG
16h 19m2 stops
6:55 am - 3:03 pmYWG-ORD
8h 08m1 stop
$517Delta
Find Deal
Sat, Jun 29 - Sun, Jun 30
1:25 pm - 11:47 pmORD-YWG
10h 22m2 stops
6:55 am - 2:44 pmYWG-ORD
7h 49m1 stop
$533Delta
Find Deal
Tue, Jul 2 - Mon, Jul 29
1:15 pm - 3:41 pmORD-YWG
2h 26mnonstop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$536United Airlines
Find Deal
Thu, Jun 27 - Sun, Jun 30
11:30 am - 10:02 pmMDW-YWG
10h 32m1 stop
10:05 am - 9:37 pmYWG-MDW
11h 32m1 stop
$547Porter Airlines
Find Deal
Mon, Jul 22 - Fri, Jul 26

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 $292 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 $490.

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 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 $919 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 WestJet for $148. WestJet proposed a round-trip connection from $380 and United Airlines from $456.

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 $444.

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 26m. 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 1:15 pm and lands at 3:41 pm.

Good to know

Low season

January

High season

February

Cheapest flight

$148
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 15% 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 $148 for a one-way ticket and $380 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 $587 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 $413 or less one-way and $668 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 10457 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They lost our luggage and didn’t return it until 15 days AFTER we got back.

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

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

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!

Unable to initiate refund/reschedule the ticket #worst experience #lost 900$

Flight was delayed for almost 3 hours. Communication of gate change was poor. Email and screen said one gate and it was a different gate from that. Gate changed first to 64 B and then to 64 C. Originally it was 68B. 64C was not communicated properly!

This was a red eye return, so I doubt there would be anyway to make it better. Other than adding beds.

Direct nonstop flight was great. Flight was delayed and the crew announced a 2h delay on the sound system. 30 min or so later I hear my name on the sound system for immediate board. Several other passangers were late too. Reason: The crew incorrectly announced a 2h delay when in reality they meant a new boarding time at 2pm.

Plenty of room in the exit row. Sat on the plane an hour before taking off.☹️ Landed late and had to wait for gate availability.

Flight was on time early arrival better entertainment good staff.everything was excellent

Delayed leaving. On arrival we were taken to the airstrip and had to get off onto an over crowed bus, not all that passengers fit. Drove around the airport for 20 + minutes. Taken off the bus told to go upstairs 3 flights then all the passengers had to walk a mile or more , those of us old there was no one to direct us to were to go. I asked several people with no answers. Once I got to baggage claim my bags were not on the right bag claim. Once again asked for help and finally someone found my bags on a different carasel. Very frustrating.

Excellent host on board. Not so friendly check-in staff. Older plane with no food or entertainment due to short flight. Friendly captain and crew.

I don’t think there was entertainment? No mention of it. It was a good flight. Only complaint was my seat cushion was not attached and kept slipping.

They canceled the flight on us very close to the flight date .

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.
6/22Sat
1 stopWestJet
17h 45mORD-YWG
$148
6/7Fri
1 stop
27h 40mORD-YWG
$183
6/7Fri
1 stop
13h 18mMDW-YWG
$207
7/21Sun
1 stop
17h 23mORD-YWG
$212
7/2Tue
1 stopAir Canada
8h 16mORD-YWG
$223
6/22Sat
2 stopsWestJet
19h 18mORD-YWG
$237
6/7Fri
2 stopsWestJet
17h 02mORD-YWG
$238
7/2Tue
2 stopsDelta
10h 22mORD-YWG
$241
7/21Sun
2 stopsDelta
28h 08mORD-YWG
$261
7/2Tue
nonstopAir Canada
2h 26mORD-YWG
$306

Search by stops

Search by airline

Search by price

Flights to Winnipeg

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

$1,090
$1,302
$490

Browse destinations: