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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Winnipeg to Chicago

(Round-trip)
Depart: Mon Nov 6 2017 Return: Wed Nov 15 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
YWG
ORD
30h 50m
2 stops
ORD
YWG
23h 42m
1 stop
Depart: Wed Nov 8 2017 Return: Wed Nov 15 2017 Trip spans 8 days
WestJet
WestJet
YWG
ORD
24h 17m
1 stop
ORD
YWG
7h 17m
1 stop
Depart: Fri Oct 27 2017 Return: Fri Nov 3 2017 Trip spans 8 days
Delta
Delta
YWG
ORD
4h 59m
1 stop
ORD
YWG
9h 17m
2 stops
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
3h 30m
1 stop
ORD
YWG
6h 21m
1 stop
Depart: Tue Nov 7 2017 Return: Thu Nov 16 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
YWG
ORD
14h 49m
2 stops
ORD
YWG
29h 14m
2 stops
Depart: Sun Nov 5 2017 Return: Thu Nov 16 2017 Trip spans 12 days
WestJet
WestJet
YWG
ORD
24h 17m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
YWG
ORD
3h 30m
1 stop
ORD
YWG
4h 02m
1 stop
Depart: Mon Nov 6 2017 Return: Thu Nov 16 2017 Trip spans 11 days
WestJet
WestJet
YWG
ORD
24h 17m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Wed Nov 8 2017 Return: Mon Nov 13 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
YWG
ORD
2h 37m
nonstop
ORD
YWG
5h 26m
1 stop
Depart: Fri Jan 12 2018 Return: Mon Jan 15 2018 Trip spans 4 days
Delta
Delta
YWG
ORD
5h 36m
1 stop
ORD
YWG
3h 45m
1 stop
Depart: Wed Nov 8 2017 Return: Fri Nov 10 2017 Trip spans 3 days
WestJet
WestJet
YWG
ORD
24h 17m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Wed Nov 8 2017 Return: Thu Nov 16 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
YWG
ORD
14h 49m
2 stops
ORD
YWG
11h 14m
2 stops
Depart: Wed Dec 20 2017 Return: Thu Dec 28 2017 Trip spans 9 days
WestJet
WestJet
YWG
ORD
19h 34m
1 stop
ORD
YWG
18h 34m
1 stop
Depart: Fri Nov 10 2017 Return: Thu Nov 16 2017 Trip spans 7 days
Delta
Delta
YWG
ORD
4h 59m
1 stop
ORD
YWG
3h 44m
1 stop
Depart: Sun Nov 5 2017 Return: Fri Nov 10 2017 Trip spans 6 days
WestJet
WestJet
YWG
ORD
26h 47m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
YWG
ORD
22h 54m
1 stop
ORD
YWG
14h 11m
2 stops
Depart: Sat Nov 11 2017 Return: Thu Nov 16 2017 Trip spans 6 days
Delta
Delta
YWG
ORD
4h 57m
1 stop
ORD
YWG
5h 25m
1 stop
Depart: Mon Nov 6 2017 Return: Fri Nov 10 2017 Trip spans 5 days
WestJet
WestJet
YWG
ORD
24h 17m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Fri Mar 2 2018 Return: Sun Mar 11 2018 Trip spans 10 days
Delta
Delta
YWG
MDW
10h 00m
2 stops
MDW
YWG
3h 43m
1 stop
Depart: Mon Feb 12 2018 Return: Sun Feb 18 2018 Trip spans 7 days
WestJet
WestJet
YWG
ORD
21h 06m
1 stop
ORD
YWG
6h 39m
1 stop
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
5533 6:48 am 9:25 am Nov 11 - Nov 18
5533 6:48 am 9:25 am Oct 30 - Nov 4
5533 6:50 am 9:27 am Oct 29 - Nov 3
5533 6:50 am 9:27 am Nov 25 - Dec 2
5533 6:50 am 9:27 am Nov 5 - Nov 24
5533 7:00 am 9:21 am Oct 7 - Oct 28
5535 12:20 pm 2:45 pm Nov 7 - Nov 21
5535 12:20 pm 2:45 pm Nov 25 - Nov 27
5535 12:20 pm 2:45 pm Nov 5 - Nov 24
5535 12:20 pm 2:45 pm Oct 29 - Nov 3
5535 12:23 pm 2:48 pm Nov 1 - Nov 1
5535 12:30 pm 2:51 pm Oct 7 - Oct 28
5632 5:25 pm 7:42 pm Oct 8 - Oct 27
5632 5:30 pm 7:55 pm Nov 5 - Nov 19
5632 5:30 pm 7:55 pm Nov 2 - Nov 2
5632 5:30 pm 7:55 pm Oct 29 - Nov 4
5632 5:30 pm 7:55 pm Nov 25 - Dec 19
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Winnipeg
$374
Destination

Chicago
only $374
only $486