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: Thu May 18 2017 Return: Tue May 23 2017 Trip spans 6 days
Delta
Delta
YWG
7:12a
MDW
12:57p
5h 45m
1 stop
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Wed Aug 16 2017 Return: Sun Aug 20 2017 Trip spans 5 days
Major Airline
Major Airline
YWG
1:00a
MDW
2:26a
1h 26m
1 stop
MDW
1:00a
YWG
2:26a
1h 26m
1 stop
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Delta
Delta
YWG
1:29p
MDW
6:07p
4h 38m
1 stop
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Sun May 21 2017 Return: Tue May 23 2017 Trip spans 3 days
Delta
Delta
YWG
3:15a
MDW
1:59p
10h 44m
2 stops
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Mon May 22 2017 Return: Wed May 24 2017 Trip spans 3 days
Delta
Delta
YWG
9:35a
MDW
3:11p
5h 36m
1 stop
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
Delta
Delta
YWG
9:46a
MDW
5:19p
7h 33m
2 stops
MDW
5:12a
YWG
9:11a
3h 59m
1 stop
Depart: Fri Jun 23 2017 Return: Sun Jun 25 2017 Trip spans 3 days
Delta
Delta
YWG
9:46a
MDW
5:19p
7h 33m
2 stops
MDW
5:10a
YWG
12:34p
7h 24m
2 stops
Depart: Fri Sep 8 2017 Return: Fri Sep 15 2017 Trip spans 8 days
Delta
Delta
YWG
1:15p
MDW
6:15p
5h 00m
1 stop
MDW
9:10a
YWG
12:41p
3h 31m
1 stop
Depart: Tue Oct 10 2017 Return: Wed Oct 25 2017 Trip spans 16 days
Delta
Delta
YWG
6:55a
MDW
10:49a
3h 54m
1 stop
MDW
9:10a
YWG
12:41p
3h 31m
1 stop
Depart: Thu Jun 15 2017 Return: Sun Jun 18 2017 Trip spans 4 days
Delta
Delta
YWG
6:58a
MDW
12:43p
5h 45m
1 stop
MDW
5:12a
YWG
9:11a
3h 59m
1 stop
Depart: Wed May 17 2017 Return: Tue May 23 2017 Trip spans 7 days
Delta
Delta
YWG
7:12a
MDW
4:35p
9h 23m
2 stops
MDW
5:10a
YWG
8:51a
3h 41m
1 stop
Depart: Tue May 23 2017 Return: Mon May 29 2017 Trip spans 7 days
Delta
Delta
YWG
1:29p
MDW
6:10p
4h 41m
1 stop
MDW
1:32p
YWG
5:30p
3h 58m
1 stop
Depart: Wed May 24 2017 Return: Tue May 30 2017 Trip spans 7 days
Delta
Delta
YWG
1:29p
MDW
6:10p
4h 41m
1 stop
MDW
2:30a
YWG
6:29a
3h 59m
1 stop
Depart: Thu May 25 2017 Return: Wed May 31 2017 Trip spans 7 days
Delta
Delta
YWG
1:29p
MDW
6:10p
4h 41m
1 stop
MDW
1:32p
YWG
5:30p
3h 58m
1 stop
Depart: Fri May 26 2017 Return: Thu Jun 1 2017 Trip spans 7 days
Delta
Delta
YWG
3:15a
MDW
7:38a
4h 23m
1 stop
MDW
8:15a
YWG
12:44p
4h 29m
1 stop
Depart: Sat May 27 2017 Return: Fri Jun 2 2017 Trip spans 7 days
Delta
Delta
YWG
9:00a
MDW
12:55p
3h 55m
1 stop
MDW
2:30a
YWG
6:29a
3h 59m
1 stop
Depart: Sun May 28 2017 Return: Sat Jun 3 2017 Trip spans 7 days
Delta
Delta
YWG
3:15a
MDW
7:38a
4h 23m
1 stop
MDW
11:20a
YWG
5:28p
6h 08m
1 stop
Depart: Mon May 29 2017 Return: Tue Jun 6 2017 Trip spans 9 days
Delta
Delta
YWG
1:29p
MDW
6:10p
4h 41m
1 stop
MDW
8:15a
YWG
12:44p
4h 29m
1 stop
Depart: Sun Jul 16 2017 Return: Thu Jul 20 2017 Trip spans 5 days
Delta
Delta
YWG
2:30a
MDW
7:40a
5h 10m
1 stop
MDW
2:30a
YWG
8:47a
6h 17m
1 stop
Depart: Wed May 10 2017 Return: Wed May 17 2017 Trip spans 8 days
Delta
Delta
YWG
1:29p
MDW
6:10p
4h 41m
1 stop
MDW
2:30a
YWG
6:29a
3h 59m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
$428
Destination

Chicago
$428
Airlines