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
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Winnipeg to Chicago Midway

(Round-trip)
Depart: Sat Mar 18 2017 Return: Sat Mar 25 2017 Trip spans 8 days
Delta
Delta
YWG
9:30a
MDW
6:08p
8h 38m
2 stops
MDW
1:29p
YWG
7:28p
5h 59m
1 stop
Depart: Tue Mar 28 2017 Return: Thu Apr 13 2017 Trip spans 17 days
Delta
Delta
YWG
9:30a
MDW
3:16p
5h 46m
1 stop
MDW
11:10a
YWG
5:53p
6h 43m
1 stop
Depart: Wed Mar 29 2017 Return: Tue Apr 4 2017 Trip spans 7 days
Delta
Delta
YWG
3:30a
MDW
7:36a
4h 06m
1 stop
MDW
8:59a
YWG
12:49p
3h 50m
1 stop
Depart: Thu Mar 30 2017 Return: Tue Apr 4 2017 Trip spans 6 days
Delta
Delta
YWG
1:23p
MDW
6:11p
4h 48m
1 stop
MDW
8:59a
YWG
12:49p
3h 50m
1 stop
Depart: Fri Mar 31 2017 Return: Tue Apr 4 2017 Trip spans 5 days
Delta
Delta
YWG
3:30a
MDW
7:36a
4h 06m
1 stop
MDW
2:25a
YWG
8:49a
6h 24m
1 stop
Depart: Sun Apr 2 2017 Return: Tue Apr 4 2017 Trip spans 3 days
Delta
Delta
YWG
1:24p
MDW
6:11p
4h 47m
1 stop
MDW
2:25a
YWG
6:51a
4h 26m
1 stop
Depart: Mon Apr 3 2017 Return: Tue Apr 4 2017 Trip spans 2 days
Delta
Delta
YWG
3:30a
MDW
7:47a
4h 17m
1 stop
MDW
8:59a
YWG
12:49p
3h 50m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 5 2017 Trip spans 2 days
Delta
Delta
YWG
3:30a
MDW
7:47a
4h 17m
1 stop
MDW
8:59a
YWG
12:49p
3h 50m
1 stop
Depart: Fri Apr 7 2017 Return: Tue Apr 11 2017 Trip spans 5 days
Delta
Delta
YWG
1:24p
MDW
6:11p
4h 47m
1 stop
MDW
5:10a
YWG
2:59p
9h 49m
2 stops
Depart: Wed May 17 2017 Return: Wed May 24 2017 Trip spans 8 days
Delta
Delta
YWG
7:25a
MDW
12:49p
5h 24m
1 stop
MDW
5:05a
YWG
8:41a
3h 36m
1 stop
Depart: Thu May 18 2017 Return: Wed May 24 2017 Trip spans 7 days
Delta
Delta
YWG
3:45a
MDW
10:37a
6h 52m
1 stop
MDW
2:25a
YWG
6:38a
4h 13m
1 stop
Depart: Thu May 25 2017 Return: Mon May 29 2017 Trip spans 5 days
Delta
Delta
YWG
3:45a
MDW
8:01a
4h 16m
1 stop
MDW
1:05p
YWG
5:25p
4h 20m
1 stop
Depart: Wed Jun 28 2017 Return: Sun Jul 2 2017 Trip spans 5 days
Delta
Delta
YWG
2:30a
MDW
7:40a
5h 10m
1 stop
MDW
11:24a
YWG
6:07p
6h 43m
1 stop
Depart: Thu Apr 6 2017 Return: Tue Apr 11 2017 Trip spans 6 days
Delta
Delta
YWG
9:30a
MDW
4:35p
7h 05m
2 stops
MDW
5:22a
YWG
12:49p
7h 27m
2 stops
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Delta
Delta
YWG
1:23p
MDW
6:11p
4h 48m
1 stop
MDW
2:30a
YWG
6:53a
4h 23m
1 stop
Depart: Fri Apr 14 2017 Return: Sun Apr 16 2017 Trip spans 3 days
Delta
Delta
YWG
3:30a
MDW
7:47a
4h 17m
1 stop
MDW
8:59a
YWG
12:49p
3h 50m
1 stop
Depart: Sun May 7 2017 Return: Wed May 17 2017 Trip spans 11 days
Delta
Delta
YWG
3:45a
MDW
10:37a
6h 52m
1 stop
MDW
11:05a
YWG
5:25p
6h 20m
1 stop
Depart: Sat Jun 17 2017 Return: Tue Jun 20 2017 Trip spans 4 days
Delta
Delta
YWG
6:55a
MDW
12:44p
5h 49m
1 stop
MDW
2:30a
YWG
6:11a
3h 41m
1 stop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
Delta
Delta
YWG
2:30a
MDW
7:40a
5h 10m
1 stop
MDW
1:15p
YWG
6:07p
4h 52m
1 stop
Depart: Sat Jun 24 2017 Return: Tue Jun 27 2017 Trip spans 4 days
Delta
Delta
YWG
1:05p
MDW
6:12p
5h 07m
1 stop
MDW
11:24a
YWG
6:07p
6h 43m
1 stop
* 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
$440
Destination

Chicago
$440
Airlines