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Find Deals on Flights 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: Wed Jun 3 2015 Return: Tue Jun 9 2015 Trip spans 7 days
Delta
Delta
MCO
9:20a
MDW
2:24p
5h 04m
1 stop
MDW
6:59a
MCO
12:25p
5h 26m
1 stop
Depart: Tue Jun 9 2015 Return: Tue Jun 23 2015 Trip spans 15 days
Delta
Delta
MCO
10:30a
MDW
5:25p
6h 55m
1 stop
MDW
5:47a
MCO
12:25p
6h 38m
1 stop
Depart: Wed Jun 10 2015 Return: Tue Jun 23 2015 Trip spans 14 days
Delta
Delta
MCO
2:58a
MDW
9:25a
6h 27m
1 stop
MDW
11:45a
MCO
5:26p
5h 41m
1 stop
Depart: Tue Jun 16 2015 Return: Tue Jun 23 2015 Trip spans 8 days
Delta
Delta
MCO
11:30a
MDW
5:25p
5h 55m
1 stop
MDW
2:05p
MCO
6:29p
4h 24m
1 stop
Depart: Wed Jun 17 2015 Return: Tue Jun 23 2015 Trip spans 7 days
Delta
Delta
MCO
4:20a
MDW
10:15a
5h 55m
1 stop
MDW
5:47a
MCO
10:44a
4h 57m
1 stop
Depart: Tue Jun 23 2015 Return: Wed Jun 24 2015 Trip spans 2 days
Delta
Delta
MCO
2:30p
MDW
7:17p
4h 47m
1 stop
MDW
3:28p
MCO
7:38p
4h 10m
1 stop
Depart: Sat Jun 13 2015 Return: Tue Jun 23 2015 Trip spans 11 days
Delta
Delta
MCO
10:05a
MDW
5:12p
7h 07m
1 stop
MDW
5:47a
MCO
11:39a
5h 52m
1 stop
Depart: Mon Jun 15 2015 Return: Tue Jun 23 2015 Trip spans 9 days
Delta
Delta
MCO
2:30p
MDW
7:17p
4h 47m
1 stop
MDW
8:30a
MCO
12:58p
4h 28m
1 stop
Depart: Mon Jun 22 2015 Return: Tue Jun 23 2015 Trip spans 2 days
Delta
Delta
MCO
2:30p
MDW
7:17p
4h 47m
1 stop
MDW
3:28p
MCO
7:38p
4h 10m
1 stop
Depart: Tue Jun 30 2015 Return: Sat Jul 4 2015 Trip spans 5 days
Delta
Delta
MCO
6:20a
MDW
12:05p
5h 45m
1 stop
MDW
12:40p
MCO
6:46p
6h 06m
1 stop
Depart: Wed Jul 1 2015 Return: Sat Jul 4 2015 Trip spans 4 days
Delta
Delta
MCO
6:20a
MDW
12:07p
5h 47m
1 stop
MDW
8:00a
MCO
12:28p
4h 28m
1 stop
Depart: Wed Jul 8 2015 Return: Tue Jul 14 2015 Trip spans 7 days
Delta
Delta
MCO
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Tue Jul 14 2015 Return: Tue Jul 21 2015 Trip spans 8 days
Delta
Delta
MCO
4:20a
MDW
10:18a
5h 58m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Jul 15 2015 Return: Tue Jul 21 2015 Trip spans 7 days
Delta
Delta
MCO
1:30p
MDW
7:14p
5h 44m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Tue Jul 21 2015 Return: Tue Jul 28 2015 Trip spans 8 days
Delta
Delta
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Jul 22 2015 Return: Tue Jul 28 2015 Trip spans 7 days
Delta
Delta
MCO
12:00p
MDW
5:28p
5h 28m
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
4:20a
MDW
9:23a
5h 03m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 11 2015 Trip spans 8 days
Delta
Delta
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 11 2015 Trip spans 7 days
Delta
Delta
MCO
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
3:28p
MCO
7:37p
4h 09m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
MCO
4:20a
MDW
8:44a
4h 24m
1 stop
MDW
12:33p
MCO
5:09p
4h 36m
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
1709 6:35 am 8:20 am Jun 13 - Jun 27
128 6:50 am 8:35 am Jul 3 - Jul 3
1531 6:50 am 8:35 am Jun 8 - Jul 2
613 6:55 am 8:40 am May 31 - Jun 5
1550 7:30 am 9:15 am Jun 7 - Aug 2
2033 7:50 am 9:40 am May 30 - Jun 6
3219 8:15 am 10:00 am May 31 - Jun 5
2095 8:45 am 10:25 am Jul 3 - Jul 3
4321 8:50 am 10:30 am Jun 7 - Jul 2
4321 8:50 am 10:30 am Jul 5 - Aug 7
4321 8:50 am 10:30 am Jun 13 - Jun 27
1647 9:55 am 11:35 am Jun 6 - Jun 6
1025 10:05 am 11:45 am Jun 13 - Jun 27
244 10:10 am 11:50 am Jul 4 - Jul 4
2029 10:45 am 12:25 pm Jul 3 - Jul 3
917 10:45 am 12:25 pm Jun 7 - Aug 2
917 10:45 am 12:25 pm Jun 8 - Jul 2
2766 10:55 am 12:40 pm May 30 - Jun 6
765 11:05 am 12:50 pm May 31 - Jun 5
2650 11:20 am 1:05 pm Jul 4 - Aug 8
2650 11:20 am 1:05 pm Jun 13 - Jun 27
174 12:10 pm 1:55 pm Jun 29 - Jul 2
174 12:10 pm 1:55 pm Jun 15 - Jun 26
174 12:10 pm 1:55 pm Jun 8 - Jun 12
581 12:10 pm 1:55 pm Jul 3 - Jul 3
4611 12:25 pm 2:10 pm Jun 13 - Jun 27
386 12:30 pm 2:15 pm Jul 4 - Jul 4
4211 12:35 pm 2:20 pm Jun 7 - Aug 2
4994 1:30 pm 3:15 pm May 23 - Jun 6
1581 1:55 pm 3:40 pm Jul 4 - Jul 4
4229 1:55 pm 3:40 pm Jun 13 - Jun 27
1144 2:05 pm 3:50 pm Jul 3 - Jul 3
1344 2:10 pm 3:55 pm Jun 7 - Aug 2
1344 2:10 pm 3:55 pm Jun 8 - Jul 2
1793 2:30 pm 4:15 pm May 30 - Jun 6
1793 2:30 pm 4:15 pm May 31 - Jun 5
1660 3:15 pm 5:00 pm Jun 13 - Jun 13
1660 3:15 pm 5:00 pm Jun 27 - Jun 27
1660 3:15 pm 5:00 pm Jun 20 - Jun 20
2100 3:15 pm 5:00 pm Jul 4 - Jul 4
568 4:00 pm 5:45 pm Jun 7 - Aug 7
1167 4:15 pm 6:05 pm Jun 13 - Jun 27
773 4:20 pm 6:05 pm Jun 6 - Jun 6
321 5:10 pm 6:55 pm May 31 - Jun 5
4828 5:15 pm 7:00 pm May 23 - Jun 6
1509 5:45 pm 7:35 pm Jun 13 - Jun 27
250 5:45 pm 7:30 pm Jul 3 - Jul 3
1506 6:05 pm 7:50 pm Jul 5 - Aug 7
1506 6:05 pm 7:50 pm Jun 7 - Jul 2
1934 6:25 pm 8:10 pm May 30 - Jun 6
874 6:25 pm 8:15 pm May 31 - Jun 5
1218 7:15 pm 9:10 pm Jul 3 - Jul 3
895 7:15 pm 9:10 pm Jul 5 - Aug 7
895 7:15 pm 9:10 pm Jun 7 - Jul 2
3342 7:20 pm 9:10 pm Jun 13 - Jun 27
999 8:40 pm 10:25 pm May 30 - Jun 6
205 9:20 pm 11:10 pm May 31 - Jun 5
2360 10:15 pm 11:55 pm Jun 13 - Jun 27
1463 10:25 pm 12:05 am Jun 7 - Jul 2
1463 10:25 pm 12:05 am Jul 5 - Aug 7
Airports
Origin

Orlando
$262
Destination

Chicago
$262
Airlines