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CHI - YWG

$137 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 6/21. 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 7/11
Thu 7/18

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 44,212,782 times on KAYAK, and here is why:

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

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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
5:55 pm - 11:38 amORD-YWG
17h 43m1 stop
8:30 am - 4:57 pmYWG-ORD
8h 27m1 stop
$337WestJet
Find Deal
Sun, Aug 25 - Thu, Sep 5
1:31 pm - 11:28 pmORD-YWG
9h 57m2 stops
6:55 am - 2:47 pmYWG-ORD
7h 52m1 stop
$350Delta
Find Deal
Wed, Jul 24 - Sat, Jul 27
5:55 pm - 2:27 pmORD-YWG
20h 32m1 stop
12:30 pm - 4:57 pmYWG-ORD
28h 27m1 stop
$352WestJet
Find Deal
Fri, Aug 23 - Fri, Aug 30
6:22 pm - 12:33 amORD-YWG
30h 11m2 stops
5:00 pm - 6:09 amYWG-ORD
13h 09m1 stop
Sat, Sep 28 - Tue, Oct 1
6:22 pm - 8:03 pmORD-YWG
25h 41m2 stops
3:20 pm - 1:19 pmYWG-ORD
21h 59m2 stops
Sat, Sep 28 - Tue, Oct 1
1:15 pm - 3:41 pmORD-YWG
2h 26mnonstop
5:10 am - 12:59 pmYWG-ORD
7h 49m1 stop
$552Air Canada
Find Deal
Thu, Jul 18 - Mon, Jul 22
8:00 am - 5:47 pmMDW-YWG
9h 47m2 stops
6:00 am - 9:37 pmYWG-MDW
15h 37m2 stops
$555Porter Airlines
Find Deal
Sat, Sep 28 - Tue, Oct 1
1:05 pm - 3:31 pmORD-YWG
2h 26mnonstop
5:10 am - 12:59 pmYWG-ORD
7h 49m1 stop
$564Air Canada
Find Deal
Sun, Aug 25 - Thu, Sep 5
5:16 am - 1:21 pmORD-YWG
8h 05m1 stop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$570United Airlines
Find Deal
Thu, Jul 11 - Sun, Jul 14
9:08 pm - 1:21 pmORD-YWG
16h 13m1 stop
2:25 pm - 4:53 pmYWG-ORD
2h 28mnonstop
$571United Airlines
Find Deal
Tue, Jul 2 - Fri, Aug 2

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 $262 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 $455.

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 $137. WestJet proposed a round-trip connection from $337 and Delta from $350.

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 $456.

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

$137
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 $137 for a one-way ticket and $337 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Winnipeg are Delta and United Airlines. With an average price for the route of $584 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $906 and an overall rating of 7.4.

  • 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 $313 or less one-way and $561 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 10277 reviews
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

Generally poor experience with excessive luggage fees. Plane seats were very uncomfortable. Flight did not take off on time, however arrived on time. Boarding seems very inefficient.

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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?

There was a mistake with the first name we only discovered at security. Air canada was unable to correct it to match then passport since it was booked through an agency. The agency could not correct it either since they need at least two hours to do that. We could not fly and lost a bunch of money. Learned my lesson about kayak.

My flight got canceled. Then AC rebooked me to a next day flight. No compensation no apology. It almost messed up my entire trip and schedule. However, all the unexpepected seems routine and ordinary to AC, so customers need to get used to.

The food was horrible the flying attendance hardly made any checks and the seats were very tied ..

I love air Canada. The staff is so helpful and friendly and attentive. I paid for extra room but chose a ser near a person who took up a lot of space which gave me less space than regular economy, I was sad I did that!

I was offered earphones at the beginning of the flight, my meal and snacks were good and the attendant was proactive with all my needs and offered seconds of drinks. She was very attentive even when there were .any demands on her

For such a long flight they should offer tea or coffee in between two meals.

No seat assignment . Last on board . Though I would not receive any boarding pass

last minute was rebooked. This rebooking made me miss my connection, added a stop in my itinerary without my approval, and had me arriving 10 hours later to my destination...for a delay that was 2 hours. To boot, my final flight from London to Athens booked me in a middle seat, where I originally booked all aisle seats. This was incredibly uncomfortable for a 24 hour journey and made me incredibly upset.

Did not appreciate “hidden fees” to check a bag for international flight and purchase a seat to be next to my spouse. Won’t choose this airline again.

The flight left over 2 hours late and caused me to miss my connecting flight. Consequently, I missed my cruise ship out of Barcelona. The cost associated with this miss was as follows: Airfare to Sicily Italy to get on the ship TWO days late - $232.30 Taxi from Airport to hotel $35 Dinner at hotel $38 Hotel in Barcelona - $208 Taxi from Sicily to hotel $70 Hotel in Sicily - $148 Prorated time missed on cruise $ 1,143

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.
6/21Fri
1 stopWestJet
26h 04mORD-YWG
$137
6/19Wed
2 stops
52h 16mORD-YWG
$145
7/20Sat
2 stopsPorter Airlines
9h 52mMDW-YWG
$236
6/18Tue
1 stopDelta
7h 17mORD-YWG
$256
6/21Fri
2 stopsPorter Airlines
10h 07mMDW-YWG
$300
6/21Fri
1 stopAir Canada
6h 47mORD-YWG
$305
6/19Wed
1 stopDelta
6h 14mORD-YWG
$310
6/22Sat
1 stopAir Canada
8h 52mORD-YWG
$335
6/21Fri
nonstopUnited Airlines
2h 26mORD-YWG
$649
6/21Fri
nonstopUnited Airlines
2h 26mORD-YWG
$823

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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.
6/13Thu
multi-stop
31h 26mORD-YWG
6/15Sat
multi-stop
8h 27mYWG-ORD
$607
6/13Thu
multi-stop
12h 12mORD-YWG
6/15Sat
multi-stop
8h 27mYWG-ORD
$644
6/13Thu
nonstopAir Canada
2h 26mORD-YWG
6/15Sat
multi-stopAir Canada
7h 24mYWG-ORD
$1,268
6/13Thu
nonstopAir Canada
2h 26mORD-YWG
6/15Sat
nonstopAir Canada
2h 28mYWG-ORD
$1,405

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Search by price

Flights to Winnipeg

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

$1,090
$1,302
$455

Browse destinations: