Find Cheap Flights from Chicago to Winnipeg (CHI - YWG)

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Fri 12/15
Fri 12/22
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Good to Know

Average Price:
$498
(avg. price over the last 2 weeks)
Good Deal:
$332
or less (round trip)

When to Book Flights from Chicago to Winnipeg

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $331 or less.
The cheapest flight from Chicago to Winnipeg was found 69 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 9% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Winnipeg Flights

How long does a flight from Chicago to Winnipeg take?
An average nonstop flight takes 2h 24m, covering a distance of 720 miles.
How many flights are there between Chicago and Winnipeg?
There are 85 (nonstop) flights between Chicago and Winnipeg per week, averaging 12 per day.
Which airlines provide the cheapest flights from Chicago to Winnipeg?
In the past 3 days, the cheapest round-trip tickets were found on United ($367), Air Canada ($433) and Multiple Airlines ($467).
Do I need a passport to fly between Chicago and Winnipeg?
Yes.
Which airlines fly most frequently between Chicago and Winnipeg?
Air Canada (4 times daily), United (4 times daily), Aer Lingus (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Winnipeg?
For Chicago to Winnipeg, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Winnipeg back to Chicago, the best deals are generally found on Tuesday, with Friday being the most expensive.

Book cheap flights from Chicago to Winnipeg (round-trip)

Airports
Origin
Chicago
$367
only
$367
$477
only
$477
Destination
Winnipeg
$367
only
$367
Thu, Feb 22
ORD
YWG
12h 26m
Mon, Feb 26
YWG
ORD
9h 19m
Trip: 5 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 11 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
YWG
Excellent 8.6

It was a wonderful flight. For such a small plane, it was asmooth takeoff and landing. The flight attendant was very friendly too.

No snack provided.

ORD
YWG
Mediocre 3.0

The trying to accommodate crew

Sitting on the plane in the gate for 1 1/2 hours, then asked to leave the plane. Flight arrival time was to be 10:00 pm, instead arrived in Winnipeg at 12:35am.

RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

RSW
EWR
Okay 5.3

Waiting

IAH
FRA
Okay 5.3

The crew wasn’t nice at all The food was bad

Thu, Apr 19
ORD
YWG
8h 07m
Fri, Apr 20
YWG
ORD
8h 25m
Trip: 2 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 20253 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
MIA
YYZ
Good 6.6

Nice, friendly crew

Sold me headphones that were very poor quality. Couldn’t use them. No snacks provided on a very long flight-all was for sale. Drink was a bit more than half a cup

YYZ
ORD
Excellent 8.0

Meh

Meh

YYZ
DUB
Good 7.3

The flights were great, on time and no problems. I was very comfortable and the food was good. FLight attendents were great except one guy who was not friendly and needed a vacation or another job.

LGA
YYZ
Okay 4.0

Direct

9:30 flight finally took odd at 11:30 .... delayed and had to set on the runway. Arrivedabd gad to wait 30 min for gate. Will be in terms mal by 1:30

YYZ
FLL
Okay 4.6

Late departure- even with snow issues have not had similar problems with WestJet

Fri, Jan 5
ORD
YWG
6h 58m
Sat, Jan 13
YWG
ORD
2h 25m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
MDW
YWG
3h 54m
Mon, Feb 26
YWG
MDW
4h 07m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 5
MDW
YWG
4h 23m
Sat, Jan 13
YWG
MDW
4h 11m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Sat, Jan 13
ORD
YWG
12h 00m
Mon, Jan 15
YWG
ORD
12h 07m
Trip: 3 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 11 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Waiting

LAX
ORD
Excellent 9.0

Not enough room for my legs, I was uncomfortable.

MIA
ORD
Excellent 9.0

That it got me to Paris safe

No outlets to charge your phone, and the tv played the same movie over and over. The meals were also cheap. Didn't like any of them. Should have flown southwest or delta.

IAH
FRA
Okay 5.3

The crew wasn’t nice at all The food was bad

ORD
YWG
Mediocre 3.0

The trying to accommodate crew

Sitting on the plane in the gate for 1 1/2 hours, then asked to leave the plane. Flight arrival time was to be 10:00 pm, instead arrived in Winnipeg at 12:35am.

Sun, Dec 17
ORD
YWG
7h 59m
Wed, Dec 20
YWG
ORD
19h 34m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 4017 reviews
Overall
8.2
Boarding
8.3
Comfort
8.0
Crew
8.6
Entertainment
7.2
Food
7.3
PHX
YYZ
Excellent 10.0

The crew, as always, was warm, welcoming and very attentive from check-in to the plane. I also enjoyed the snacks that were served.

PVR
YYC
Excellent 8.0

suitcase was busted up on the bottom totally missing 1 wheel

YUL
MCO
Excellent 10.0

Fantastic flight!

YVR
YYJ
Good 6.0

The overhead bins are now too small for a large number of carry on luggage that meets the criteria of carry on. If you wheel your now over sized carry on to the gate they will stow it below for free. If you check it they charge you $26.00 knowing it won't fit in the bins anyway.

YVR
HNL
Excellent 8.6

Order ahead food was easy and selection was tasty

Bring a book! Apps to have your entertainment on individual devices is a bad idea.

Thu, Jan 11
ORD
YWG
6h 13m
Mon, Jan 15
YWG
ORD
12h 07m
Trip: 5 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 20253 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
MSP
YYZ
Excellent 8.6

Crew and flight were great

Not great food, but that's ok.

YYZ
FLL
Okay 4.6

Late departure- even with snow issues have not had similar problems with WestJet

YYC
YYZ
Excellent 10.0

Flight cancelled due to weather, the workers made it seamless.

Had to tack on extra expenses for food while waiting for the next flight. Should have gotten some type of vouchers to cover meals at the very least during cancellations. That would be next level.

TPE
YVR
Mediocre 3.3

The plane was quite new, and that's pretty much it.

The food is unsuitable for human consumption and so as some of the crew were unsuitable for the position.

YYZ
DUB
Good 7.3

The flights were great, on time and no problems. I was very comfortable and the food was good. FLight attendents were great except one guy who was not friendly and needed a vacation or another job.

Fri, Feb 23
ORD
YWG
12h 26m
Mon, Feb 26
YWG
ORD
2h 26m
Trip: 4 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 11 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Waiting

LAX
EWR
Good 7.6

I had the row to myself. Smooth flight. On time. Actually we got there early.

My arm rest would not stay up. Flight attendant almost seemed rude. Might have been just her tone. She seemed annoyed. I could be wrong.

LAX
YVR
Excellent 8.0

Checking in was simple with no problems. They made the process easy. Very courteous!

LAX
NRT
Good 7.3

Good price

Stink in the plane

MIA
ORD
Excellent 9.0

That it got me to Paris safe

No outlets to charge your phone, and the tv played the same movie over and over. The meals were also cheap. Didn't like any of them. Should have flown southwest or delta.

Sat, Jan 13
ORD
YWG
7h 19m
Mon, Jan 15
YWG
ORD
2h 25m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 23
MDW
YWG
3h 54m
Mon, Feb 26
YWG
MDW
4h 07m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jan 11
MDW
YWG
5h 14m
Mon, Jan 15
YWG
MDW
4h 48m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Thu, Mar 15
ORD
YWG
5h 36m
Sat, Mar 17
YWG
ORD
2h 26m
Trip: 3 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 20253 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Excellent 8.0

Meh

Meh

YYZ
FLL
Okay 4.6

Late departure- even with snow issues have not had similar problems with WestJet

YYZ
YEG
Excellent 10.0

Food was great

Nothing

MIA
YYZ
Good 6.6

Nice, friendly crew

Sold me headphones that were very poor quality. Couldn’t use them. No snacks provided on a very long flight-all was for sale. Drink was a bit more than half a cup

YYZ
DUB
Good 7.3

The flights were great, on time and no problems. I was very comfortable and the food was good. FLight attendents were great except one guy who was not friendly and needed a vacation or another job.

Sat, Jan 13
ORD
YWG
14h 22m
Sun, Jan 14
YWG
ORD
6h 52m
Trip: 2 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 11 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
MIA
ORD
Excellent 9.0

That it got me to Paris safe

No outlets to charge your phone, and the tv played the same movie over and over. The meals were also cheap. Didn't like any of them. Should have flown southwest or delta.

LAX
YVR
Excellent 8.0

Checking in was simple with no problems. They made the process easy. Very courteous!

ORD
LAS
Okay 4.0

The crew was helpful and friendly, my flight was inexpensive

The seats were incredibly uncomfortable! Also, many people did not understand how to turn off the televisions, so it was pretty distracting to have so many monitors going when we all trying to sleep.

ORD
YWG
Mediocre 3.0

The trying to accommodate crew

Sitting on the plane in the gate for 1 1/2 hours, then asked to leave the plane. Flight arrival time was to be 10:00 pm, instead arrived in Winnipeg at 12:35am.

PUJ
EWR
Good 7.3

The flight was very hot and uncomfortable

Thu, Jan 11
ORD
YWG
2h 24m
Mon, Jan 15
YWG
ORD
6h 47m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 16
MDW
YWG
6h 25m
Mon, Feb 19
YWG
MDW
5h 04m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

LGA
YUL
Excellent 8.0

it was easy to navigate .

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Fri, Feb 16
ORD
YWG
2h 25m
Mon, Feb 19
YWG
ORD
2h 26m
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 20253 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
ORD
Excellent 8.0

Meh

Meh

MSP
YYZ
Excellent 8.6

Crew and flight were great

Not great food, but that's ok.

YYZ
YEG
Excellent 10.0

Food was great

Nothing

YYC
YYZ
Excellent 10.0

Flight cancelled due to weather, the workers made it seamless.

Had to tack on extra expenses for food while waiting for the next flight. Should have gotten some type of vouchers to cover meals at the very least during cancellations. That would be next level.

MIA
YYZ
Good 6.6

Nice, friendly crew

Sold me headphones that were very poor quality. Couldn’t use them. No snacks provided on a very long flight-all was for sale. Drink was a bit more than half a cup

Wed, Mar 14
MDW
YWG
3h 50m
Wed, Mar 21
YWG
MDW
5h 15m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Mon, Dec 18
ORD
YWG
7h 19m
Sat, Jan 6
YWG
ORD
8h 02m
Trip: 20 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 15
MDW
YWG
6h 30m
Sat, Mar 17
YWG
MDW
4h 11m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

LGA
YUL
Excellent 8.0

it was easy to navigate .

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.