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: Wed Aug 30 2017 Return: Tue Sep 5 2017 Trip spans 7 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
7h 56m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
Major Airline
Major Airline
YWG
MDW
1h 26m
nonstop
MDW
YWG
1h 26m
nonstop
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
American Airlines
American Airlines
YWG
ORD
14h 13m
2 stops
ORD
YWG
10h 34m
2 stops
Depart: Sat Jul 1 2017 Return: Sat Jul 8 2017 Trip spans 8 days
Delta
Delta
YWG
ORD
4h 48m
1 stop
ORD
YWG
11h 29m
2 stops
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
7h 56m
1 stop
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
5h 05m
1 stop
MDW
YWG
6h 47m
1 stop
Depart: Wed May 31 2017 Return: Fri Jun 2 2017 Trip spans 3 days
American Airlines
American Airlines
YWG
ORD
13h 10m
2 stops
ORD
YWG
9h 04m
2 stops
Depart: Thu Aug 10 2017 Return: Wed Aug 16 2017 Trip spans 7 days
WestJet
WestJet
YWG
ORD
12h 19m
2 stops
ORD
YWG
7h 59m
1 stop
Depart: Sat Jul 1 2017 Return: Sat Jul 8 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
4h 54m
1 stop
MDW
YWG
5h 06m
1 stop
Depart: Fri Jul 21 2017 Return: Sun Jul 30 2017 Trip spans 10 days
WestJet
WestJet
YWG
ORD
12h 19m
2 stops
ORD
YWG
7h 59m
1 stop
Depart: Wed May 31 2017 Return: Wed Jun 14 2017 Trip spans 15 days
Major Airline
Major Airline
YWG
MDW
1h 26m
nonstop
MDW
YWG
1h 26m
nonstop
Depart: Mon Aug 28 2017 Return: Sun Sep 3 2017 Trip spans 7 days
Delta
Delta
YWG
MDW
5h 25m
1 stop
MDW
YWG
4h 22m
1 stop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
WestJet
WestJet
YWG
ORD
24h 38m
1 stop
ORD
YWG
26h 38m
1 stop
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3760 6:51 am 9:15 am Jun 8 - Jul 2
5257 7:09 am 9:29 am Jun 5 - Jun 7
5257 7:09 am 9:29 am May 20 - Jun 3
5257 7:09 am 9:33 am Jun 4 - Jun 4
4231 11:49 am 2:10 pm Jun 8 - Jul 4
4231 11:49 am 2:10 pm Jun 10 - Jul 1
5377 12:35 pm 2:56 pm May 31 - Jun 7
5377 12:35 pm 2:56 pm May 21 - May 30
4065 5:24 pm 7:45 pm Jun 8 - Jun 30
* 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
$382
Destination

Chicago
only $382
only $389