Find Cheap Flights from Winnipeg to Chicago O'Hare International (YWG - ORD)

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Fri 12/15
Fri 12/22
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Good to Know

Average Price:
$520
(avg. price over the last 2 weeks)
Good Deal:
$403
or less (round trip)

When to Book Flights from Winnipeg to Chicago O'Hare International

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 $402 or less.
The cheapest flight from Winnipeg to Chicago O'Hare International was found 39 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 24% 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 O'Hare International Flights

How long does a flight from Winnipeg to Chicago O'Hare International take?
An average nonstop flight takes 4h 19m, covering a distance of 706 miles.
How many flights are there between Winnipeg and Chicago O'Hare International?
There are 98 (nonstop) flights between Winnipeg and Chicago O'Hare International per week, averaging 14 per day.
Which airlines provide the cheapest flights from Winnipeg to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($377) and Delta ($409)
Do I need a passport to fly between Winnipeg and Chicago O'Hare International?
Yes.
Which airlines fly most frequently between Winnipeg and Chicago O'Hare International?
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 O'Hare International?
For Winnipeg to Chicago O'Hare International, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago O'Hare International back to Winnipeg, the best deals are generally found on Saturday, with Friday being the most expensive.

Book cheap flights from Winnipeg to Chicago O'Hare International (round-trip)

Airports
Origin
Winnipeg
$377
only
$377
Destination
Chicago
$377
only
$377
Wed, Feb 14
YWG
ORD
12h 42m
Wed, Feb 21
ORD
YWG
10h 56m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 13
YWG
ORD
4h 19m
Thu, Jan 18
ORD
YWG
7h 18m
Trip: 6 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

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.

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.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

Fri, Feb 23
YWG
ORD
5h 33m
Sat, Mar 3
ORD
YWG
5h 34m
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
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
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

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.

*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.