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 May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
WestJet
WestJet
YWG
ORD
28h 01m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Mon Oct 23 2017 Return: Fri Oct 27 2017 Trip spans 5 days
Major Airline
Major Airline
YWG
ORD
1h 24m
nonstop
ORD
YWG
1h 24m
nonstop
Depart: Sun May 14 2017 Return: Wed May 17 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
5h 36m
1 stop
MDW
YWG
4h 29m
1 stop
Depart: Mon Jul 17 2017 Return: Sat Jul 22 2017 Trip spans 6 days
United
United
YWG
ORD
2h 21m
nonstop
ORD
YWG
2h 19m
nonstop
Depart: Wed May 31 2017 Return: Tue Jun 6 2017 Trip spans 7 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
7h 56m
1 stop
Depart: Wed May 31 2017 Return: Tue Jun 6 2017 Trip spans 7 days
Delta
Delta
YWG
MDW
5h 36m
1 stop
MDW
YWG
3h 59m
1 stop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
7h 33m
2 stops
MDW
YWG
3h 59m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Sun Jul 16 2017 Return: Thu Jul 20 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
5h 10m
1 stop
MDW
YWG
6h 17m
1 stop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
8h 00m
1 stop
Depart: Tue Aug 8 2017 Return: Fri Aug 11 2017 Trip spans 4 days
Delta
Delta
YWG
MDW
5h 10m
1 stop
MDW
YWG
3h 41m
1 stop
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
WestJet
WestJet
YWG
ORD
28h 03m
1 stop
ORD
YWG
7h 56m
1 stop
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Delta
Delta
YWG
MDW
3h 54m
1 stop
MDW
YWG
3h 31m
1 stop
Depart: Sun Apr 30 2017 Return: Fri May 5 2017 Trip spans 6 days
WestJet
WestJet
YWG
ORD
24h 40m
1 stop
ORD
YWG
6h 29m
1 stop
Depart: Sun Oct 8 2017 Return: Tue Oct 10 2017 Trip spans 3 days
Delta
Delta
YWG
MDW
3h 54m
1 stop
MDW
YWG
3h 31m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
5h 45m
1 stop
MDW
YWG
5h 40m
1 stop
Depart: Sun Apr 30 2017 Return: Sun May 7 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
5h 46m
1 stop
MDW
YWG
3h 41m
1 stop
Depart: Thu Aug 17 2017 Return: Mon Aug 21 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
3h 54m
1 stop
MDW
YWG
4h 52m
1 stop
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3760 7:00 am 9:24 am Apr 23 - Apr 30
5257 7:00 am 9:24 am Apr 22 - May 4
5257 7:09 am 9:29 am May 6 - Jun 3
3991 12:25 pm 2:46 pm Apr 30 - Apr 30
5377 12:25 pm 2:46 pm Apr 24 - May 4
5377 12:25 pm 2:46 pm Apr 22 - May 3
5377 12:35 pm 2:56 pm May 5 - May 26
5377 12:35 pm 2:56 pm May 6 - May 24
5377 12:35 pm 2:56 pm May 27 - Jun 7
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
$375
Destination

Chicago
only $375
only $431
Airlines Airline reviews

4 travelers who booked a flight from Winnipeg to Chicago rated their chosen airlines with an average of 10.0.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
10.0
Food
10.0
Entertainment
10.0