Find Deals on 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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Winnipeg to Chicago

(Round-trip)
Depart: Tue Jun 13 2017 Return: Wed Jun 14 2017 Trip spans 2 days
WestJet
WestJet
YWG
ORD
7h 32m
1 stop
ORD
YWG
7h 39m
1 stop
Depart: Mon Aug 7 2017 Return: Fri Aug 11 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
9h 11m
2 stops
ORD
YWG
11h 29m
2 stops
Depart: Wed Jul 26 2017 Return: Wed Aug 2 2017 Trip spans 8 days
WestJet
WestJet
YWG
ORD
8h 08m
1 stop
ORD
YWG
7h 39m
1 stop
Depart: Wed Jul 26 2017 Return: Mon Jul 31 2017 Trip spans 6 days
Delta
Delta
YWG
ORD
11h 48m
2 stops
ORD
YWG
6h 44m
1 stop
Depart: Sat Apr 15 2017 Return: Sat Apr 29 2017 Trip spans 15 days
WestJet
WestJet
YWG
ORD
7h 37m
1 stop
ORD
YWG
26h 40m
1 stop
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
Delta
Delta
YWG
MDW
4h 06m
1 stop
MDW
YWG
4h 23m
1 stop
Depart: Thu May 25 2017 Return: Mon May 29 2017 Trip spans 5 days
WestJet
WestJet
YWG
ORD
7h 49m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Mon Mar 27 2017 Return: Sat Apr 1 2017 Trip spans 6 days
Delta
Delta
YWG
MDW
4h 48m
1 stop
MDW
YWG
4h 24m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
WestJet
WestJet
YWG
ORD
9h 40m
2 stops
ORD
YWG
11h 14m
2 stops
Depart: Fri Apr 21 2017 Return: Sun Apr 23 2017 Trip spans 3 days
Delta
Delta
YWG
MDW
5h 41m
1 stop
MDW
YWG
6h 43m
1 stop
Depart: Thu May 11 2017 Return: Mon May 15 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
6h 44m
1 stop
ORD
YWG
6h 20m
1 stop
Depart: Thu May 11 2017 Return: Mon May 15 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
6h 52m
1 stop
MDW
YWG
4h 20m
1 stop
Depart: Thu May 25 2017 Return: Mon May 29 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
5h 33m
1 stop
MDW
YWG
4h 20m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
6h 52m
1 stop
MDW
YWG
6h 43m
1 stop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
5h 10m
1 stop
MDW
YWG
6h 43m
1 stop
Depart: Wed Jul 26 2017 Return: Mon Jul 31 2017 Trip spans 6 days
Delta
Delta
YWG
MDW
4h 02m
1 stop
MDW
YWG
6h 43m
1 stop
Depart: Thu Aug 17 2017 Return: Mon Aug 21 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
3h 56m
1 stop
ORD
YWG
6h 44m
1 stop
Depart: Thu Aug 17 2017 Return: Mon Aug 21 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
5h 10m
1 stop
MDW
YWG
4h 52m
1 stop
Depart: Tue Feb 28 2017 Return: Fri Mar 3 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
10h 05m
2 stops
MDW
YWG
9h 49m
2 stops
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
5701 6:30 am 9:00 am Mar 8 - Mar 8
5701 6:30 am 9:00 am Mar 6 - Mar 7
3760 7:00 am 9:24 am Apr 4 - Apr 4
5257 7:00 am 9:24 am Apr 5 - May 4
3760 7:05 am 9:40 am Mar 10 - Mar 10
3760 7:05 am 9:40 am Mar 12 - Mar 24
3760 7:05 am 9:40 am Mar 11 - Mar 11
3760 7:05 am 9:40 am Mar 14 - Mar 25
3760 7:05 am 9:40 am Mar 26 - Apr 3
5701 7:05 am 9:40 am Mar 9 - Mar 9
5377 12:25 pm 2:46 pm Apr 5 - Apr 12
5377 12:25 pm 2:46 pm Apr 4 - May 4
3991 12:30 pm 2:53 pm Mar 10 - Mar 10
3991 12:30 pm 2:53 pm Mar 26 - Apr 3
3991 12:30 pm 2:53 pm Mar 29 - Mar 29
3991 12:30 pm 2:53 pm Mar 9 - Mar 11
3991 12:30 pm 2:53 pm Mar 14 - Mar 23
3991 12:30 pm 2:53 pm Mar 12 - Mar 24
5706 12:30 pm 2:53 pm Mar 25 - Mar 25
5245 12:37 pm 3:00 pm Mar 8 - Mar 8
5245 12:37 pm 3:00 pm Feb 24 - Mar 6
5245 12:37 pm 3:00 pm Mar 2 - Mar 7
* 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.

We compile tonnes of data for you
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Winnipeg
$393
Destination

Chicago
only $393
only $442