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

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Good to Know

Average Price:
$492
(avg. price over the last 2 weeks)
Good Deal:
$410
or less (round trip)

When to Book Flights from Winnipeg to Chicago

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 $410 or less.
The cheapest flight from Winnipeg to Chicago was found 60 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 16% 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 Winnipeg to Chicago Flights

How long does a flight from Winnipeg to Chicago take?
An average nonstop flight takes 2h 25m, covering a distance of 720 miles.
How many flights are there between Winnipeg and Chicago?
There are 98 (nonstop) flights between Winnipeg and Chicago per week, averaging 14 per day.
Which airlines provide the cheapest flights from Winnipeg to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($359) and Delta ($409)
Do I need a passport to fly between Winnipeg and Chicago?
Yes.
Which airlines fly most frequently between Winnipeg and Chicago?
Air Canada (6 times daily), United (5 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 Winnipeg to Chicago?
For Winnipeg to Chicago, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Winnipeg, the best deals are generally found on Saturday, with Sunday being the most expensive.

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

Airports
Origin
Winnipeg
$359
only
$359
Destination
Chicago
$359
only
$359
$409
only
$409
Tue, Jan 23
YWG
ORD
11h 59m
Tue, Mar 6
ORD
YWG
11h 06m
Trip: 43 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 13
YWG
MDW
4h 25m
Thu, Jan 18
MDW
YWG
4h 23m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

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.

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.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

Fri, Jan 19
YWG
ORD
12h 37m
Tue, Mar 6
ORD
YWG
11h 06m
Trip: 47 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Jan 22
YWG
ORD
4h 33m
Thu, Mar 8
ORD
YWG
7h 00m
Trip: 46 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

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.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

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.

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.

Sun, Jan 21
YWG
ORD
12h 22m
Tue, Mar 6
ORD
YWG
11h 15m
Trip: 45 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Feb 23
YWG
MDW
5h 10m
Sat, Mar 3
MDW
YWG
3h 39m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
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.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

Tue, Jan 23
YWG
ORD
11h 59m
Mon, Mar 5
ORD
YWG
10h 56m
Trip: 42 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 29
YWG
ORD
5h 28m
Sun, Apr 1
ORD
YWG
6h 25m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
YYZ
Excellent 10.0

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

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Mon, Jan 22
YWG
ORD
2h 25m
Tue, Mar 6
ORD
YWG
11h 15m
Trip: 44 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 29
YWG
ORD
5h 28m
Sun, Apr 1
ORD
YWG
6h 25m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 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.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

GSO
ATL
Excellent 10.0

Plane nice and comfortable

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

Wed, Jan 24
YWG
ORD
2h 25m
Tue, Mar 6
ORD
YWG
11h 15m
Trip: 42 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 14
YWG
ORD
7h 22m
Wed, Feb 21
ORD
YWG
4h 14m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

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.

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.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
YYZ
Excellent 10.0

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

Thu, Jan 25
YWG
ORD
2h 25m
Tue, Mar 6
ORD
YWG
11h 15m
Trip: 41 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Dec 25
YWG
MDW
5h 53m
Fri, Dec 29
MDW
YWG
4h 25m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

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.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
YYZ
Excellent 10.0

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

Sat, Jan 20
YWG
ORD
6h 52m
Tue, Mar 6
ORD
YWG
11h 15m
Trip: 46 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 19
YWG
ORD
12h 37m
Mon, Mar 5
ORD
YWG
10h 56m
Trip: 46 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 9
YWG
MDW
5h 05m
Sun, Jun 17
MDW
YWG
6h 59m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

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.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Tue, Jan 23
YWG
ORD
11h 59m
Thu, Mar 8
ORD
YWG
2h 27m
Trip: 45 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Dec 25
YWG
MDW
5h 53m
Tue, Jan 2
MDW
YWG
4h 25m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

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.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

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.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

Tue, Jan 23
YWG
ORD
11h 59m
Wed, Mar 7
ORD
YWG
7h 06m
Trip: 44 days
Overall 0.0 Poor
Based on 0 reviews
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*
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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.