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Find Deals on Flights from Orlando All airports to Chicago Midway (ORL - MDW)

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

Book cheap flights from Orlando All airports to Chicago Midway

(Round-trip)
Depart: Tue Jul 14 2015 Return: Tue Jul 21 2015 Trip spans 8 days
Delta
Delta
MCO
11:30a
MDW
5:20p
5h 50m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Mon Jul 20 2015 Return: Tue Jul 21 2015 Trip spans 2 days
Delta
Delta
MCO
11:30a
MDW
5:20p
5h 50m
1 stop
MDW
3:05a
MCO
9:25a
6h 20m
1 stop
Depart: Tue Jul 21 2015 Return: Wed Jul 22 2015 Trip spans 2 days
Delta
Delta
MCO
10:30a
MDW
3:52p
5h 22m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Tue Jul 28 2015 Return: Tue Aug 4 2015 Trip spans 8 days
Delta
Delta
MCO
10:00a
MDW
2:53p
4h 53m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Sun Aug 2 2015 Return: Tue Aug 4 2015 Trip spans 3 days
Delta
Delta
MCO
1:20a
MDW
6:20a
5h 00m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Mon Aug 3 2015 Return: Tue Aug 4 2015 Trip spans 2 days
Delta
Delta
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Tue Aug 4 2015 Return: Wed Aug 5 2015 Trip spans 2 days
Delta
Delta
MCO
10:23a
MDW
6:35p
8h 12m
1 stop
MDW
8:25a
MCO
3:20p
6h 55m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 18 2015 Trip spans 14 days
Delta
Delta
MCO
9:30a
MDW
3:52p
6h 22m
1 stop
MDW
3:10a
MCO
8:20a
5h 10m
1 stop
Depart: Thu Aug 6 2015 Return: Tue Aug 11 2015 Trip spans 6 days
Delta
Delta
MCO
11:30a
MDW
5:20p
5h 50m
1 stop
MDW
2:30a
MCO
8:19a
5h 49m
1 stop
Depart: Tue Aug 11 2015 Return: Wed Aug 12 2015 Trip spans 2 days
Delta
Delta
MCO
4:20a
MDW
9:23a
5h 03m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Aug 12 2015 Return: Mon Aug 17 2015 Trip spans 6 days
Delta
Delta
MCO
5:30a
MDW
12:07p
6h 37m
1 stop
MDW
2:14p
MCO
7:37p
5h 23m
1 stop
Depart: Tue Aug 18 2015 Return: Sat Aug 22 2015 Trip spans 5 days
Delta
Delta
MCO
7:53a
MDW
12:58p
5h 05m
1 stop
MDW
8:00a
MCO
1:25p
5h 25m
1 stop
Depart: Wed Aug 19 2015 Return: Sat Aug 22 2015 Trip spans 4 days
Delta
Delta
MCO
8:25a
MDW
2:22p
5h 57m
1 stop
MDW
8:00a
MCO
1:25p
5h 25m
1 stop
Depart: Tue Aug 25 2015 Return: Thu Aug 27 2015 Trip spans 3 days
Delta
Delta
MCO
2:20a
MDW
6:12a
3h 52m
1 stop
MDW
8:19a
MCO
12:27p
4h 08m
1 stop
Depart: Wed Aug 26 2015 Return: Thu Aug 27 2015 Trip spans 2 days
Delta
Delta
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Thu Aug 27 2015 Return: Fri Aug 28 2015 Trip spans 2 days
Delta
Delta
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Fri Aug 28 2015 Return: Sun Aug 30 2015 Trip spans 3 days
Delta
Delta
MCO
4:20a
MDW
10:05a
5h 45m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Sun Aug 30 2015 Return: Mon Aug 31 2015 Trip spans 2 days
Delta
Delta
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
MDW
3:32p
MCO
7:35p
4h 03m
1 stop
Depart: Wed Sep 2 2015 Return: Wed Sep 9 2015 Trip spans 8 days
Delta
Delta
MCO
2:30p
MDW
7:07p
4h 37m
1 stop
MDW
6:25a
MCO
11:25a
5h 00m
1 stop
Depart: Wed Sep 16 2015 Return: Tue Sep 22 2015 Trip spans 7 days
Delta
Delta
MCO
1:20a
MDW
6:18a
4h 58m
1 stop
MDW
5:55a
MCO
11:25a
5h 30m
1 stop
Select an airline:  Southwest
Direct flights ORL to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1709 6:35 am 8:20 am Jul 11 - Aug 8
2135 6:45 am 8:35 am Aug 10 - Sep 4
1531 6:50 am 8:35 am Jul 10 - Jul 17
1531 6:50 am 8:35 am Jul 21 - Aug 7
1550 7:30 am 9:15 am Jun 28 - Aug 2
4321 8:50 am 10:30 am Jul 11 - Aug 8
4321 8:50 am 10:30 am Jul 10 - Aug 7
1025 10:05 am 11:45 am Jul 11 - Aug 1
1025 10:05 am 11:45 am Aug 8 - Aug 8
917 10:45 am 12:25 pm Jun 28 - Aug 2
917 10:45 am 12:25 pm Jul 10 - Aug 7
2650 11:20 am 1:05 pm Jul 4 - Aug 8
1146 11:45 am 1:30 pm Aug 9 - Sep 25
174 12:10 pm 1:55 pm Jul 6 - Aug 7
4611 12:25 pm 2:10 pm Jul 11 - Aug 1
718 12:25 pm 2:10 pm Aug 8 - Aug 8
4211 12:35 pm 2:20 pm Jun 28 - Aug 2
50 12:50 pm 2:35 pm Aug 9 - Sep 4
4229 1:55 pm 3:40 pm Jul 11 - Aug 8
1344 2:10 pm 3:55 pm Jul 10 - Aug 7
1344 2:10 pm 3:55 pm Jun 28 - Aug 2
1660 3:15 pm 5:00 pm Jul 11 - Aug 8
136 3:20 pm 5:10 pm Aug 10 - Aug 10
136 3:20 pm 5:10 pm Aug 9 - Aug 16
568 4:00 pm 5:45 pm Jun 28 - Aug 7
1167 4:15 pm 6:05 pm Jul 11 - Aug 1
1167 4:15 pm 6:05 pm Aug 8 - Aug 8
2095 5:10 pm 7:00 pm Aug 9 - Sep 4
1509 5:45 pm 7:35 pm Jul 11 - Aug 1
1506 6:05 pm 7:50 pm Jul 10 - Aug 7
6366 6:45 pm 8:35 pm Aug 8 - Aug 8
566 6:50 pm 8:40 pm Aug 10 - Sep 4
1496 7:00 pm 8:50 pm Aug 9 - Aug 30
895 7:15 pm 9:10 pm Jul 10 - Aug 7
153 7:20 pm 9:10 pm Aug 8 - Aug 8
3342 7:20 pm 9:10 pm Jul 18 - Aug 1
246 8:50 pm 10:40 pm Aug 9 - Sep 4
2360 10:15 pm 11:55 pm Jul 11 - Aug 1
1463 10:25 pm 12:05 am Jul 12 - Jul 17
1463 10:25 pm 12:05 am Aug 2 - Aug 7
1463 10:25 pm 12:05 am Jul 26 - Jul 31
1463 10:25 pm 12:05 am Jul 19 - Jul 24
Airports
Origin

Orlando
$185
Destination

Chicago
$185
Airlines