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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: Tue Apr 14 2015 Return: Sat Apr 18 2015 Trip spans 5 days
Delta
Delta
ORL
4:30a
MDW
8:41a
4h 11m
1 stop
MDW
8:15a
ORL
12:23p
4h 08m
1 stop
Depart: Wed Apr 15 2015 Return: Mon Apr 20 2015 Trip spans 6 days
Delta
Delta
ORL
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
12:34p
ORL
5:26p
4h 52m
1 stop
Depart: Thu Apr 16 2015 Return: Sat Apr 18 2015 Trip spans 3 days
Delta
Delta
ORL
4:30a
MDW
8:41a
4h 11m
1 stop
MDW
8:15a
ORL
12:23p
4h 08m
1 stop
Depart: Fri Apr 17 2015 Return: Mon Apr 20 2015 Trip spans 4 days
Delta
Delta
ORL
3:30a
MDW
8:41a
5h 11m
1 stop
MDW
12:00p
ORL
5:24p
5h 24m
1 stop
Depart: Sat Apr 18 2015 Return: Mon Apr 20 2015 Trip spans 3 days
Delta
Delta
ORL
5:20a
MDW
11:55a
6h 35m
1 stop
MDW
12:00p
ORL
4:24p
4h 24m
1 stop
Depart: Tue Apr 21 2015 Return: Sun Apr 26 2015 Trip spans 6 days
Delta
Delta
ORL
4:20a
MDW
9:20a
5h 00m
1 stop
MDW
3:05a
ORL
10:29a
7h 24m
1 stop
Depart: Wed Apr 22 2015 Return: Sun Apr 26 2015 Trip spans 5 days
Delta
Delta
ORL
6:00a
MDW
12:55p
6h 55m
1 stop
MDW
3:05a
ORL
9:22a
6h 17m
1 stop
Depart: Thu Apr 23 2015 Return: Sun Apr 26 2015 Trip spans 4 days
Delta
Delta
ORL
4:30a
MDW
10:55a
6h 25m
1 stop
MDW
3:05a
ORL
10:29a
7h 24m
1 stop
Depart: Fri Apr 24 2015 Return: Mon Apr 27 2015 Trip spans 4 days
Delta
Delta
ORL
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
3:05a
ORL
8:18a
5h 13m
1 stop
Depart: Sun Apr 26 2015 Return: Thu Apr 30 2015 Trip spans 5 days
Delta
Delta
ORL
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
3:05a
ORL
9:22a
6h 17m
1 stop
Depart: Mon Apr 27 2015 Return: Fri May 1 2015 Trip spans 5 days
Delta
Delta
ORL
1:45p
MDW
7:09p
5h 24m
1 stop
MDW
6:00a
ORL
11:37a
5h 37m
1 stop
Depart: Tue Apr 28 2015 Return: Sat May 2 2015 Trip spans 5 days
Delta
Delta
ORL
4:30a
MDW
10:55a
6h 25m
1 stop
MDW
5:56a
ORL
12:24p
6h 28m
1 stop
Depart: Thu Apr 30 2015 Return: Sun May 3 2015 Trip spans 4 days
Delta
Delta
ORL
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
2:00p
ORL
7:20p
5h 20m
1 stop
Depart: Fri May 1 2015 Return: Sun May 3 2015 Trip spans 3 days
Delta
Delta
ORL
11:15a
MDW
4:58p
5h 43m
1 stop
MDW
2:00p
ORL
7:20p
5h 20m
1 stop
Depart: Tue May 5 2015 Return: Sat May 9 2015 Trip spans 5 days
Delta
Delta
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
MDW
1:59p
ORL
6:30p
4h 31m
1 stop
Depart: Wed May 6 2015 Return: Sat May 9 2015 Trip spans 4 days
Delta
Delta
ORL
4:20a
MDW
8:47a
4h 27m
1 stop
MDW
1:59p
ORL
6:30p
4h 31m
1 stop
Depart: Thu May 7 2015 Return: Sat May 9 2015 Trip spans 3 days
Delta
Delta
ORL
7:15a
MDW
12:24p
5h 09m
1 stop
MDW
1:59p
ORL
6:30p
4h 31m
1 stop
Depart: Fri May 8 2015 Return: Sun May 10 2015 Trip spans 3 days
Delta
Delta
ORL
2:20a
MDW
6:23a
4h 03m
1 stop
MDW
2:45a
ORL
8:07a
5h 22m
1 stop
Depart: Sat May 9 2015 Return: Sat May 16 2015 Trip spans 8 days
Delta
Delta
ORL
2:30p
MDW
7:07p
4h 37m
1 stop
MDW
5:56a
ORL
10:30a
4h 34m
1 stop
Depart: Thu Apr 9 2015 Return: Mon Apr 13 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
ORL
4:10p
MDW
6:40a
14h 30m
1 stop
MDW
6:30a
ORL
2:58p
8h 28m
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
1624 6:50 am 8:55 am Mar 14 - Apr 4
1538 6:55 am 9:00 am Apr 7 - Apr 7
581 6:55 am 9:00 am Mar 8 - Apr 6
613 6:55 am 8:40 am Apr 8 - May 22
2442 7:20 am 9:10 am Mar 14 - Apr 4
2033 7:50 am 9:40 am Apr 11 - May 16
3219 8:15 am 10:00 am Apr 8 - May 22
3221 9:10 am 11:00 am Apr 7 - Apr 7
3834 9:10 am 11:00 am Mar 22 - Apr 6
3834 9:10 am 11:00 am Mar 15 - Mar 20
3834 9:10 am 11:00 am Mar 8 - Mar 13
968 9:55 am 11:45 am Mar 14 - Mar 28
968 9:55 am 11:45 am Apr 4 - Apr 4
1647 10:00 am 11:40 am Apr 11 - May 16
4316 10:20 am 12:15 pm Mar 8 - Apr 5
512 10:25 am 12:20 pm Mar 9 - Mar 27
3848 10:35 am 12:30 pm Apr 7 - Apr 7
512 10:35 am 12:30 pm Mar 30 - Apr 6
2501 10:55 am 12:50 pm Mar 14 - Apr 4
2766 10:55 am 12:40 pm Apr 11 - May 16
765 11:05 am 12:50 pm Apr 8 - May 22
2497 11:45 am 1:40 pm Mar 14 - Apr 4
1227 11:55 am 1:45 pm Apr 7 - Apr 7
328 11:55 am 1:45 pm Mar 8 - Apr 6
1957 1:10 pm 3:00 pm Mar 14 - Apr 4
4994 1:30 pm 3:15 pm Apr 11 - Jun 6
3767 1:55 pm 3:45 pm Apr 7 - Apr 7
4124 1:55 pm 3:45 pm Mar 8 - Apr 5
638 1:55 pm 3:45 pm Mar 9 - Apr 6
1287 2:10 pm 4:00 pm Mar 14 - Apr 4
1793 2:30 pm 4:15 pm Apr 8 - May 22
1793 2:30 pm 4:15 pm Apr 11 - May 16
2446 3:20 pm 5:10 pm Mar 14 - Apr 4
2270 4:10 pm 6:00 pm Mar 14 - Apr 4
2330 4:35 pm 6:25 pm Mar 8 - Apr 6
3384 4:35 pm 6:25 pm Apr 7 - Apr 7
773 4:35 pm 6:20 pm Apr 11 - May 16
973 5:00 pm 6:50 pm Mar 14 - Apr 4
321 5:10 pm 6:55 pm Apr 8 - May 22
4828 5:15 pm 7:00 pm Apr 11 - Jun 6
1622 5:25 pm 7:15 pm Apr 7 - Apr 7
646 5:25 pm 7:15 pm Mar 8 - Apr 6
1844 6:05 pm 7:55 pm Apr 7 - Apr 7
824 6:05 pm 7:55 pm Mar 8 - Apr 6
1934 6:25 pm 8:10 pm Apr 11 - May 16
2282 6:25 pm 8:15 pm Mar 14 - Apr 4
874 6:25 pm 8:15 pm Apr 8 - May 22
2637 7:00 pm 8:55 pm Mar 14 - Apr 4
999 8:40 pm 10:25 pm Apr 11 - May 16
205 9:20 pm 11:10 pm Apr 8 - May 22
1303 10:05 pm 11:55 pm Apr 7 - Apr 7
388 10:05 pm 11:55 pm Mar 8 - Mar 15
388 10:05 pm 11:55 pm Mar 16 - Apr 6
4183 10:15 pm 12:05 am Mar 14 - Apr 4
Airports
Origin

Orlando
$250
Destination

Chicago
$250