Browse Origins:
Browse Destinations:

Find Flight Deals 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: Wed Jun 10 2015 Return: Tue Jun 30 2015 Trip spans 21 days
Delta
Delta
ORL
2:30p
MDW
7:17p
4h 47m
1 stop
MDW
8:29a
ORL
1:32p
5h 03m
1 stop
Depart: Sat Jun 13 2015 Return: Tue Jun 23 2015 Trip spans 11 days
Delta
Delta
ORL
12:00p
MDW
5:12p
5h 12m
1 stop
MDW
2:05p
ORL
7:38p
5h 33m
1 stop
Depart: Tue Jun 16 2015 Return: Tue Jun 23 2015 Trip spans 8 days
Delta
Delta
ORL
9:59a
MDW
2:55p
4h 56m
1 stop
MDW
3:28p
ORL
7:38p
4h 10m
1 stop
Depart: Wed Jun 17 2015 Return: Tue Jun 23 2015 Trip spans 7 days
Delta
Delta
ORL
5:25a
MDW
10:15a
4h 50m
1 stop
MDW
5:47a
ORL
10:44a
4h 57m
1 stop
Depart: Tue Jun 23 2015 Return: Wed Jun 24 2015 Trip spans 2 days
Delta
Delta
ORL
11:30a
MDW
5:25p
5h 55m
1 stop
MDW
3:28p
ORL
7:38p
4h 10m
1 stop
Depart: Tue Jun 30 2015 Return: Wed Jul 1 2015 Trip spans 2 days
Delta
Delta
ORL
2:30p
MDW
7:15p
4h 45m
1 stop
MDW
5:55a
ORL
11:38a
5h 43m
1 stop
Depart: Wed Jul 1 2015 Return: Wed Jul 8 2015 Trip spans 8 days
Delta
Delta
ORL
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
2:14p
ORL
7:37p
5h 23m
1 stop
Depart: Wed Jul 8 2015 Return: Tue Jul 14 2015 Trip spans 7 days
Delta
Delta
ORL
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
9:53a
ORL
2:40p
4h 47m
1 stop
Depart: Tue Jul 14 2015 Return: Wed Jul 15 2015 Trip spans 2 days
Delta
Delta
ORL
3:00a
MDW
9:23a
6h 23m
1 stop
MDW
2:30a
ORL
8:29a
5h 59m
1 stop
Depart: Wed Jul 15 2015 Return: Tue Jul 21 2015 Trip spans 7 days
Delta
Delta
ORL
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
3:28p
ORL
7:37p
4h 09m
1 stop
Depart: Wed Jul 22 2015 Return: Tue Jul 28 2015 Trip spans 7 days
Delta
Delta
ORL
11:30a
MDW
5:20p
5h 50m
1 stop
MDW
2:14p
ORL
7:37p
5h 23m
1 stop
Depart: Tue Jul 28 2015 Return: Tue Aug 4 2015 Trip spans 8 days
Delta
Delta
ORL
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
3:05a
ORL
8:21a
5h 16m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 11 2015 Trip spans 8 days
Delta
Delta
ORL
5:30a
MDW
10:18a
4h 48m
1 stop
MDW
3:05a
ORL
7:27a
4h 22m
1 stop
Depart: Wed Aug 5 2015 Return: Tue Aug 11 2015 Trip spans 7 days
Delta
Delta
ORL
2:30p
MDW
7:14p
4h 44m
1 stop
MDW
2:00a
ORL
7:27a
5h 27m
1 stop
Depart: Tue Aug 11 2015 Return: Tue Aug 18 2015 Trip spans 8 days
Delta
Delta
ORL
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
1:55p
ORL
6:34p
4h 39m
1 stop
Depart: Wed Aug 12 2015 Return: Tue Aug 18 2015 Trip spans 7 days
Delta
Delta
ORL
7:20a
MDW
12:07p
4h 47m
1 stop
MDW
6:10a
ORL
10:22a
4h 12m
1 stop
Depart: Tue Aug 18 2015 Return: Wed Aug 19 2015 Trip spans 2 days
Delta
Delta
ORL
10:30a
MDW
3:36p
5h 06m
1 stop
MDW
1:55p
ORL
7:22p
5h 27m
1 stop
Depart: Wed Aug 19 2015 Return: Sat Aug 22 2015 Trip spans 4 days
Delta
Delta
ORL
1:20a
MDW
6:04a
4h 44m
1 stop
MDW
2:00a
ORL
7:22a
5h 22m
1 stop
Depart: Wed Aug 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
Delta
Delta
ORL
4:30a
MDW
10:12a
5h 42m
1 stop
MDW
9:50a
ORL
2:22p
4h 32m
1 stop
Depart: Mon Sep 7 2015 Return: Thu Sep 10 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
ORL
9:00a
MDW
5:45p
8h 45m
1 stop
MDW
4:00a
ORL
7:08a
27h 08m
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 Jun 13 - Jun 27
1531 6:50 am 8:35 am Jun 8 - Jul 2
613 6:55 am 8:40 am May 31 - Jun 5
613 6:55 am 8:40 am May 21 - May 29
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
3219 8:15 am 10:00 am May 21 - May 29
4321 8:50 am 10:30 am Jun 13 - Jun 27
4321 8:50 am 10:30 am Jun 7 - Jul 2
1647 9:55 am 11:35 am Jun 6 - Jun 6
1647 10:00 am 11:40 am May 30 - May 30
1025 10:05 am 11:45 am Jun 13 - Jun 27
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 21 - May 29
765 11:05 am 12:50 pm May 31 - Jun 5
2650 11:20 am 1:05 pm Jun 13 - Jun 27
174 12:10 pm 1:55 pm Jun 15 - Jun 26
174 12:10 pm 1:55 pm Jun 29 - Jul 2
174 12:10 pm 1:55 pm Jun 8 - Jun 12
4611 12:25 pm 2:10 pm Jun 13 - Jun 27
4211 12:35 pm 2:20 pm Jun 7 - Aug 2
4994 1:30 pm 3:15 pm May 23 - Jun 6
4229 1:55 pm 3:40 pm Jun 13 - Jun 27
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 21 - May 29
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 20 - Jun 20
1660 3:15 pm 5:00 pm Jun 27 - Jun 27
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
773 4:35 pm 6:20 pm May 30 - May 30
321 5:10 pm 6:55 pm May 21 - May 29
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
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
874 6:25 pm 8:15 pm May 21 - May 29
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 21 - May 29
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
Airports
Origin

Orlando
$286
Destination

Chicago
$286