Find Cheap 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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Book cheap flights from Winnipeg to Chicago Midway

(Round-trip)
Depart: Wed Jun 21 2017 Return: Sat Jun 24 2017 Trip spans 4 days
Delta
Delta
YWG
9:46a
MDW
5:19p
7h 33m
2 stops
MDW
1:13p
YWG
6:15p
5h 02m
1 stop
Depart: Tue Jul 11 2017 Return: Fri Jul 14 2017 Trip spans 4 days
Delta
Delta
YWG
2:40a
MDW
6:19a
3h 39m
1 stop
MDW
2:30a
YWG
6:27a
3h 57m
1 stop
Depart: Sun Jul 16 2017 Return: Wed Jul 26 2017 Trip spans 11 days
Delta
Delta
YWG
2:40a
MDW
6:24a
3h 44m
1 stop
MDW
2:30a
YWG
8:51a
6h 21m
1 stop
Depart: Sat Jul 22 2017 Return: Wed Jul 26 2017 Trip spans 5 days
Delta
Delta
YWG
1:14p
MDW
6:15p
5h 01m
1 stop
MDW
5:02a
YWG
8:51a
3h 49m
1 stop
Depart: Thu Jul 27 2017 Return: Sat Jul 29 2017 Trip spans 3 days
Delta
Delta
YWG
2:40a
MDW
6:19a
3h 39m
1 stop
MDW
1:13p
YWG
6:19p
5h 06m
1 stop
Depart: Mon Jul 31 2017 Return: Thu Aug 3 2017 Trip spans 4 days
Delta
Delta
YWG
1:14p
MDW
6:18p
5h 04m
1 stop
MDW
6:59a
YWG
12:34p
5h 35m
1 stop
Depart: Tue Aug 1 2017 Return: Fri Aug 4 2017 Trip spans 4 days
Delta
Delta
YWG
2:40a
MDW
6:19a
3h 39m
1 stop
MDW
2:30a
YWG
6:27a
3h 57m
1 stop
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
Delta
Delta
YWG
7:20a
MDW
12:49p
5h 29m
1 stop
MDW
1:10p
YWG
6:11p
5h 01m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Delta
Delta
YWG
2:40a
MDW
8:20a
5h 40m
2 stops
MDW
1:13p
YWG
6:20p
5h 07m
1 stop
Depart: Thu Jul 20 2017 Return: Mon Jul 24 2017 Trip spans 5 days
Delta
Delta
YWG
2:40a
MDW
7:35a
4h 55m
1 stop
MDW
1:13p
YWG
6:20p
5h 07m
1 stop
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
Delta
Delta
YWG
2:30a
MDW
7:35a
5h 05m
1 stop
MDW
1:13p
YWG
6:16p
5h 03m
1 stop
Depart: Fri Jun 16 2017 Return: Sun Jun 18 2017 Trip spans 3 days
Delta
Delta
YWG
9:46a
MDW
3:11p
5h 25m
1 stop
MDW
11:07a
YWG
6:16p
7h 09m
1 stop
Depart: Wed Aug 16 2017 Return: Sun Aug 20 2017 Trip spans 5 days
Delta
Delta
YWG
9:20a
MDW
3:03p
5h 43m
1 stop
MDW
1:15p
YWG
6:07p
4h 52m
1 stop
Depart: Thu Aug 17 2017 Return: Sun Aug 20 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: Wed Jun 7 2017 Return: Sun Jun 11 2017 Trip spans 5 days
Delta
Delta
YWG
9:35a
MDW
3:11p
5h 36m
1 stop
MDW
1:32p
YWG
5:30p
3h 58m
1 stop
Depart: Thu Jun 8 2017 Return: Tue Jun 13 2017 Trip spans 6 days
Delta
Delta
YWG
3:15a
MDW
7:38a
4h 23m
1 stop
MDW
5:11a
YWG
9:11a
4h 00m
1 stop
Depart: Wed May 31 2017 Return: Mon Jun 5 2017 Trip spans 6 days
Delta
Delta
YWG
3:15a
MDW
1:59p
10h 44m
2 stops
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Fri Jun 2 2017 Return: Mon Jun 5 2017 Trip spans 4 days
Delta
Delta
YWG
9:35a
MDW
3:11p
5h 36m
1 stop
MDW
2:30a
YWG
6:29a
3h 59m
1 stop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Delta
Delta
YWG
1:29p
MDW
6:07p
4h 38m
1 stop
MDW
2:30a
YWG
6:29a
3h 59m
1 stop
Depart: Tue May 30 2017 Return: Thu Jun 1 2017 Trip spans 3 days
$1136
Select
Delta
Delta
YWG
9:35a
MDW
6:20p
8h 45m
2 stops
MDW
9:00a
YWG
5:30p
8h 30m
2 stops
* 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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Winnipeg
$439
Destination

Chicago
$439
Airlines