Find Deals on Flights from Winnipeg to Chicago Midway (YWG - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
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 Midway

(Round-trip)
Depart: Mon Jan 9 2017 Return: Fri Jan 20 2017 Trip spans 12 days
Delta
Delta
YWG
12:15p
MDW
5:09p
4h 54m
1 stop
MDW
1:20a
YWG
6:55a
5h 35m
1 stop
Depart: Sat Feb 18 2017 Return: Thu Feb 23 2017 Trip spans 6 days
Delta
Delta
YWG
1:15a
MDW
5:50a
4h 35m
1 stop
MDW
7:50a
YWG
11:44a
3h 54m
1 stop
Depart: Sun Feb 5 2017 Return: Tue Feb 7 2017 Trip spans 3 days
Delta
Delta
YWG
1:30a
MDW
5:55a
4h 25m
1 stop
MDW
7:20a
YWG
4:54p
9h 34m
2 stops
Depart: Sat Feb 25 2017 Return: Mon Feb 27 2017 Trip spans 3 days
Delta
Delta
YWG
5:30a
MDW
12:25p
6h 55m
1 stop
MDW
12:05p
YWG
4:47p
4h 42m
1 stop
Depart: Tue Apr 4 2017 Return: Mon Apr 10 2017 Trip spans 7 days
Delta
Delta
YWG
7:25a
MDW
12:46p
5h 21m
1 stop
MDW
1:05p
YWG
5:28p
4h 23m
1 stop
Depart: Wed Jan 18 2017 Return: Mon Jan 23 2017 Trip spans 6 days
Delta
Delta
YWG
7:30a
MDW
2:05p
6h 35m
1 stop
MDW
10:29a
YWG
4:54p
6h 25m
1 stop
Depart: Fri Dec 16 2016 Return: Sun Dec 18 2016 Trip spans 3 days
Delta
Delta
YWG
12:15p
MDW
4:56p
4h 41m
1 stop
MDW
1:25a
YWG
6:48a
5h 23m
1 stop
Depart: Wed Dec 28 2016 Return: Sat Dec 31 2016 Trip spans 4 days
Delta
Delta
YWG
12:35p
MDW
5:05p
4h 30m
1 stop
MDW
1:25a
YWG
6:45a
5h 20m
1 stop
Depart: Thu Dec 29 2016 Return: Sun Jan 1 2017 Trip spans 4 days
Delta
Delta
YWG
12:35p
MDW
5:23a
16h 48m
1 stop
MDW
7:55a
YWG
4:53p
8h 58m
1 stop
Depart: Sat Dec 17 2016 Return: Mon Dec 19 2016 Trip spans 3 days
Delta
Delta
YWG
1:30a
MDW
5:05p
15h 35m
1 stop
MDW
2:55p
YWG
6:57p
4h 02m
1 stop
Depart: Tue Dec 20 2016 Return: Mon Jan 2 2017 Trip spans 14 days
Delta
Delta
YWG
12:35p
MDW
5:05p
4h 30m
1 stop
MDW
1:25a
YWG
6:48a
5h 23m
1 stop
Depart: Fri Dec 23 2016 Return: Thu Jan 5 2017 Trip spans 14 days
Delta
Delta
YWG
12:35p
MDW
5:05p
4h 30m
1 stop
MDW
2:00a
YWG
10:20a
8h 20m
2 stops
* 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
$439
Destination

Chicago
$439
Airlines