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: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Major Airline
Major Airline
YWG
ORD
1h 24m
2 stops
ORD
YWG
1h 24m
2 stops
Depart: Fri Jul 14 2017 Return: Mon Jul 17 2017 Trip spans 4 days
United
United
YWG
ORD
2h 21m
nonstop
ORD
YWG
2h 19m
nonstop
Depart: Mon Aug 28 2017 Return: Fri Sep 1 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
5h 25m
1 stop
MDW
YWG
4h 02m
1 stop
Depart: Thu Nov 30 2017 Return: Sun Dec 3 2017 Trip spans 4 days
Major Airline
Major Airline
YWG
ORD
1h 24m
nonstop
ORD
YWG
1h 24m
nonstop
Depart: Wed Aug 30 2017 Return: Fri Sep 1 2017 Trip spans 3 days
Delta
Delta
YWG
MDW
5h 59m
2 stops
MDW
YWG
4h 02m
1 stop
Depart: Wed Aug 23 2017 Return: Sat Aug 26 2017 Trip spans 4 days
Major Airline
Major Airline
YWG
ORD
1h 24m
nonstop
ORD
YWG
1h 24m
nonstop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Delta
Delta
YWG
MDW
6h 53m
2 stops
MDW
YWG
4h 01m
1 stop
Depart: Thu Oct 12 2017 Return: Wed Oct 18 2017 Trip spans 7 days
Major Airline
Major Airline
YWG
ORD
1h 24m
nonstop
ORD
YWG
1h 24m
nonstop
Depart: Mon Oct 2 2017 Return: Sun Oct 15 2017 Trip spans 14 days
Delta
Delta
YWG
MDW
5h 05m
1 stop
MDW
YWG
7h 22m
2 stops
Depart: Mon Jul 31 2017 Return: Mon Aug 7 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
5h 04m
1 stop
MDW
YWG
5h 35m
1 stop
Depart: Thu Aug 17 2017 Return: Sun Aug 20 2017 Trip spans 4 days
Major Airline
Major Airline
YWG
ORD
10h 14m
nonstop
ORD
YWG
10h 29m
nonstop
Depart: Fri Jun 30 2017 Return: Tue Jul 4 2017 Trip spans 5 days
Delta
Delta
YWG
ORD
3h 44m
1 stop
ORD
YWG
12h 34m
2 stops
Depart: Fri Jun 23 2017 Return: Fri Jun 30 2017 Trip spans 8 days
Delta
Delta
YWG
MDW
5h 45m
1 stop
MDW
YWG
3h 57m
1 stop
Direct flights YWG to CHI on United
Flight # Depart YWG Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3760 6:26 am 8:50 am Jul 5 - Aug 14
3760 6:26 am 8:50 am Jul 4 - Jul 4
3760 6:51 am 9:15 am Jul 8 - Aug 13
3760 6:51 am 9:15 am Jun 21 - Jul 2
4231 11:49 am 2:10 pm Jul 5 - Aug 14
4231 11:49 am 2:10 pm Jun 24 - Jul 1
4231 11:49 am 2:10 pm Jun 21 - Jul 4
5808 5:10 pm 7:31 pm Jul 2 - Aug 14
4065 5:24 pm 7:45 pm Jun 21 - Jun 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Winnipeg
$397
Destination

Chicago
only $397
only $445
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