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: Tue Nov 21 2017 Return: Tue Nov 28 2017 Trip spans 8 days
WestJet
WestJet
YWG
ORD
17h 23m
1 stop
ORD
YWG
7h 57m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
United
United
YWG
ORD
9h 13m
2 stops
ORD
YWG
8h 25m
2 stops
Depart: Sat Feb 3 2018 Return: Sat Feb 10 2018 Trip spans 8 days
Delta
Delta
YWG
MDW
7h 56m
2 stops
MDW
YWG
9h 00m
2 stops
Depart: Sun Feb 4 2018 Return: Tue Feb 6 2018 Trip spans 3 days
WestJet
WestJet
YWG
ORD
17h 30m
1 stop
ORD
YWG
6h 39m
1 stop
Depart: Tue Nov 21 2017 Return: Tue Nov 28 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
9h 42m
2 stops
MDW
YWG
11h 16m
2 stops
Depart: Fri Dec 1 2017 Return: Fri Jan 12 2018 Trip spans 43 days
WestJet
WestJet
YWG
ORD
19h 34m
1 stop
ORD
YWG
7h 04m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
3h 42m
1 stop
MDW
YWG
4h 12m
1 stop
Depart: Fri Sep 1 2017 Return: Sat Sep 9 2017 Trip spans 9 days
WestJet
WestJet
YWG
ORD
27h 33m
1 stop
ORD
YWG
5h 49m
1 stop
Depart: Sat Oct 21 2017 Return: Sun Oct 29 2017 Trip spans 9 days
Delta
Delta
YWG
MDW
5h 02m
1 stop
MDW
YWG
6h 29m
1 stop
Depart: Wed Nov 8 2017 Return: Sun Nov 12 2017 Trip spans 5 days
WestJet
WestJet
YWG
ORD
26h 47m
1 stop
ORD
YWG
26h 46m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
YWG
MDW
3h 47m
1 stop
MDW
YWG
3h 47m
1 stop
Depart: Wed Aug 30 2017 Return: Sat Sep 9 2017 Trip spans 11 days
WestJet
WestJet
YWG
ORD
21h 55m
1 stop
ORD
YWG
5h 49m
1 stop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
7h 02m
1 stop
MDW
YWG
3h 39m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
4h 54m
1 stop
ORD
YWG
4h 44m
1 stop
Depart: Wed Aug 30 2017 Return: Sat Sep 9 2017 Trip spans 11 days
Delta
Delta
YWG
MDW
5h 40m
2 stops
MDW
YWG
7h 11m
2 stops
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3760 6:45 am 9:06 am Aug 16 - Sep 5
4389 7:00 am 9:24 am Sep 6 - Sep 6
5533 7:00 am 9:24 am Sep 7 - Oct 4
5533 7:00 am 9:24 am Sep 9 - Sep 30
4231 11:52 am 2:13 pm Aug 16 - Sep 5
5535 12:30 pm 2:54 pm Sep 6 - Sep 27
5808 4:45 pm 7:02 pm Aug 16 - Sep 1
5808 4:45 pm 7:02 pm Sep 5 - Sep 5
5633 5:25 pm 7:45 pm Sep 7 - Oct 4
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Winnipeg
$410
Destination

Chicago
only $410
only $451
Airlines Airline reviews

5 travelers who booked a flight from Winnipeg to Chicago rated their chosen airlines with an average of 9.5.

Overall
9.6
Boarding
9.6
Crew
9.6
Comfort
9.6
Food
8.8
Entertainment
9.6