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Find Flight Deals from Orlando to Chicago Midway (MCO - MDW)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Sat May 16 2015 Return: Tue May 19 2015 Trip spans 4 days
Delta
Delta
MCO
1:45p
MDW
7:08p
5h 23m
1 stop
MDW
3:10a
MCO
8:00a
4h 50m
1 stop
Depart: Tue May 19 2015 Return: Sat May 23 2015 Trip spans 5 days
Delta
Delta
MCO
10:00a
MDW
2:55p
4h 55m
1 stop
MDW
1:59p
MCO
6:15p
4h 16m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
MCO
7:10a
MDW
12:56p
5h 46m
1 stop
MDW
1:59p
MCO
6:15p
4h 16m
1 stop
Depart: Sat May 23 2015 Return: Tue May 26 2015 Trip spans 4 days
Delta
Delta
MCO
7:10a
MDW
12:55p
5h 45m
1 stop
MDW
10:26a
MCO
2:44p
4h 18m
1 stop
Depart: Tue May 26 2015 Return: Sat May 30 2015 Trip spans 5 days
Delta
Delta
MCO
2:30p
MDW
7:10p
4h 40m
1 stop
MDW
11:44a
MCO
4:28p
4h 44m
1 stop
Depart: Wed May 27 2015 Return: Sat May 30 2015 Trip spans 4 days
Delta
Delta
MCO
4:20a
MDW
8:47a
4h 27m
1 stop
MDW
8:35a
MCO
12:52p
4h 17m
1 stop
Depart: Sat May 30 2015 Return: Tue Jun 2 2015 Trip spans 4 days
Delta
Delta
MCO
12:25p
MDW
4:57p
4h 32m
1 stop
MDW
5:25a
MCO
9:47a
4h 22m
1 stop
Depart: Wed Jun 3 2015 Return: Tue Jun 9 2015 Trip spans 7 days
Delta
Delta
MCO
12:20p
MDW
4:59p
4h 39m
1 stop
MDW
3:28p
MCO
7:38p
4h 10m
1 stop
Depart: Tue Jun 9 2015 Return: Tue Jun 30 2015 Trip spans 22 days
Delta
Delta
MCO
2:30p
MDW
7:17p
4h 47m
1 stop
MDW
5:47a
MCO
10:41a
4h 54m
1 stop
Depart: Wed Jun 17 2015 Return: Wed Jun 24 2015 Trip spans 8 days
Delta
Delta
MCO
9:30a
MDW
2:30p
5h 00m
1 stop
MDW
2:05p
MCO
6:29p
4h 24m
1 stop
Depart: Wed Jul 1 2015 Return: Sat Jul 4 2015 Trip spans 4 days
Delta
Delta
MCO
9:30a
MDW
2:29p
4h 59m
1 stop
MDW
8:00a
MCO
1:31p
5h 31m
1 stop
Depart: Tue Jul 28 2015 Return: Wed Jul 29 2015 Trip spans 2 days
Delta
Delta
MCO
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Aug 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
Delta
Delta
MCO
7:30a
MDW
11:42a
4h 12m
1 stop
MDW
8:30a
MCO
12:22p
3h 52m
1 stop
Depart: Tue Sep 1 2015 Return: Tue Sep 8 2015 Trip spans 8 days
Delta
Delta
MCO
7:30a
MDW
11:42a
4h 12m
1 stop
MDW
8:30a
MCO
12:22p
3h 52m
1 stop
Depart: Wed Sep 2 2015 Return: Tue Sep 8 2015 Trip spans 7 days
Delta
Delta
MCO
7:30a
MDW
11:42a
4h 12m
1 stop
MDW
8:30a
MCO
12:22p
3h 52m
1 stop
Depart: Tue Jun 16 2015 Return: Sat Jun 20 2015 Trip spans 5 days
Delta
Delta
MCO
4:20a
MDW
10:15a
5h 55m
1 stop
MDW
2:05p
MCO
7:36p
5h 31m
1 stop
Depart: Mon May 18 2015 Return: Wed May 20 2015 Trip spans 3 days
Delta
Delta
MCO
2:30p
MDW
7:10p
4h 40m
1 stop
MDW
5:07a
MCO
12:32p
7h 25m
1 stop
Depart: Thu May 21 2015 Return: Sat May 23 2015 Trip spans 3 days
Delta
Delta
MCO
3:30a
MDW
8:47a
5h 17m
1 stop
MDW
12:30p
MCO
5:28p
4h 58m
1 stop
Depart: Sun May 24 2015 Return: Tue May 26 2015 Trip spans 3 days
Delta
Delta
MCO
4:20a
MDW
8:45a
4h 25m
1 stop
MDW
5:25a
MCO
9:47a
4h 22m
1 stop
Depart: Thu May 28 2015 Return: Sat May 30 2015 Trip spans 3 days
Delta
Delta
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
MDW
11:44a
MCO
4:28p
4h 44m
1 stop
Select an airline:  Southwest
Direct flights MCO to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
613 6:55 am 8:40 am May 26 - Jun 5
613 6:55 am 8:40 am Apr 8 - May 22
390 7:20 am 9:05 am May 24 - May 24
3783 7:25 am 9:10 am May 25 - May 25
2033 7:50 am 9:40 am May 30 - Jun 6
2033 7:50 am 9:40 am Apr 11 - May 16
2087 7:50 am 9:40 am May 23 - May 23
2429 8:00 am 9:45 am May 25 - May 25
3219 8:15 am 10:00 am Apr 8 - May 22
3219 8:15 am 10:00 am May 26 - Jun 5
3219 9:10 am 10:55 am May 24 - May 24
1647 10:00 am 11:40 am May 30 - May 30
1647 10:00 am 11:40 am Apr 11 - May 16
1663 10:00 am 11:40 am May 23 - May 23
4211 10:20 am 12:05 pm May 25 - May 25
2766 10:55 am 12:40 pm May 30 - Jun 6
2766 10:55 am 12:40 pm Apr 11 - May 16
2798 10:55 am 12:40 pm May 23 - May 23
765 11:05 am 12:50 pm Apr 8 - May 22
765 11:05 am 12:50 pm May 26 - Jun 5
384 12:20 pm 2:05 pm May 24 - May 24
4994 1:30 pm 3:15 pm Apr 11 - Jun 6
1793 2:30 pm 4:15 pm Apr 8 - May 22
1793 2:30 pm 4:15 pm Apr 11 - May 16
1793 2:30 pm 4:15 pm May 30 - Jun 6
1793 2:30 pm 4:15 pm May 26 - Jun 5
3211 2:30 pm 4:15 pm May 25 - May 25
580 2:35 pm 4:20 pm May 23 - May 23
580 2:35 pm 4:20 pm May 24 - May 24
736 4:35 pm 6:20 pm May 23 - May 23
773 4:35 pm 6:20 pm Apr 11 - May 16
773 4:35 pm 6:20 pm May 30 - May 30
321 5:10 pm 6:55 pm May 26 - Jun 5
321 5:10 pm 6:55 pm Apr 8 - May 22
321 5:15 pm 7:00 pm May 24 - May 25
4828 5:15 pm 7:00 pm Apr 11 - Jun 6
1934 6:25 pm 8:10 pm Apr 11 - May 16
1934 6:25 pm 8:10 pm May 30 - Jun 6
874 6:25 pm 8:15 pm Apr 8 - May 22
874 6:25 pm 8:15 pm May 26 - Jun 5
874 6:25 pm 8:15 pm May 24 - May 24
2906 6:35 pm 8:25 pm May 25 - May 25
197 8:35 pm 10:25 pm May 24 - May 24
999 8:40 pm 10:25 pm May 30 - Jun 6
999 8:40 pm 10:25 pm Apr 11 - May 16
997 9:00 pm 10:45 pm May 23 - May 23
205 9:20 pm 11:10 pm May 26 - Jun 5
205 9:20 pm 11:10 pm Apr 8 - May 22
488 9:20 pm 11:10 pm May 25 - May 25
Airports
Origin

Orlando
$286
Destination

Chicago
$286
Airlines