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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: Wed Jan 7 2015 Return: Sun Jan 11 2015 Trip spans 5 days
Delta
Delta
ORL
3:20a
MDW
8:24a
5h 04m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Thu Jan 8 2015 Return: Sun Jan 11 2015 Trip spans 4 days
Delta
Delta
ORL
6:30a
MDW
10:40a
4h 10m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Tue Jan 13 2015 Return: Mon Jan 19 2015 Trip spans 7 days
Delta
Delta
ORL
12:20a
MDW
5:16a
4h 56m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Wed Jan 14 2015 Return: Mon Jan 19 2015 Trip spans 6 days
Delta
Delta
ORL
9:14a
MDW
1:57p
4h 43m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Thu Jan 15 2015 Return: Sun Jan 18 2015 Trip spans 4 days
Delta
Delta
ORL
6:30a
MDW
10:40a
4h 10m
1 stop
MDW
11:50a
ORL
4:27p
4h 37m
1 stop
Depart: Fri Jan 16 2015 Return: Sun Jan 18 2015 Trip spans 3 days
Delta
Delta
ORL
12:20a
MDW
5:16a
4h 56m
1 stop
MDW
8:40a
ORL
2:26p
5h 46m
1 stop
Depart: Tue Jan 20 2015 Return: Tue Jan 27 2015 Trip spans 8 days
Delta
Delta
ORL
12:30p
MDW
5:34p
5h 04m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Wed Jan 21 2015 Return: Tue Jan 27 2015 Trip spans 7 days
Delta
Delta
ORL
2:20a
MDW
7:29a
5h 09m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Thu Jan 22 2015 Return: Sun Jan 25 2015 Trip spans 4 days
Delta
Delta
ORL
6:30a
MDW
10:40a
4h 10m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Fri Jan 23 2015 Return: Sun Jan 25 2015 Trip spans 3 days
Delta
Delta
ORL
3:20a
MDW
8:24a
5h 04m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Tue Jan 27 2015 Return: Wed Feb 4 2015 Trip spans 9 days
Delta
Delta
ORL
2:20a
MDW
9:05a
6h 45m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Wed Jan 28 2015 Return: Tue Feb 3 2015 Trip spans 7 days
Delta
Delta
ORL
9:30a
MDW
3:55p
6h 25m
1 stop
MDW
12:59p
ORL
5:11p
4h 12m
1 stop
Depart: Thu Jan 29 2015 Return: Sun Feb 1 2015 Trip spans 4 days
Delta
Delta
ORL
4:30a
MDW
9:05a
4h 35m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Fri Jan 30 2015 Return: Mon Feb 2 2015 Trip spans 4 days
Delta
Delta
ORL
12:20a
MDW
5:16a
4h 56m
1 stop
MDW
11:31a
ORL
4:27p
4h 56m
1 stop
Depart: Thu Feb 5 2015 Return: Sun Feb 8 2015 Trip spans 4 days
Delta
Delta
ORL
6:30a
MDW
10:40a
4h 10m
1 stop
MDW
2:10a
ORL
6:28a
4h 18m
1 stop
Depart: Fri Feb 6 2015 Return: Mon Feb 9 2015 Trip spans 4 days
Delta
Delta
ORL
12:30p
MDW
5:34p
5h 04m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Sat Jan 10 2015 Return: Sun Jan 11 2015 Trip spans 2 days
Delta
Delta
ORL
9:16a
MDW
4:29p
7h 13m
1 stop
MDW
7:05a
ORL
1:25p
6h 20m
1 stop
Depart: Sat Jan 17 2015 Return: Sun Jan 18 2015 Trip spans 2 days
Delta
Delta
ORL
2:20a
MDW
7:28a
5h 08m
1 stop
MDW
8:40a
ORL
1:25p
4h 45m
1 stop
Depart: Sat Jan 24 2015 Return: Mon Jan 26 2015 Trip spans 3 days
Delta
Delta
ORL
12:30p
MDW
5:33p
5h 03m
1 stop
MDW
10:20a
ORL
2:26p
4h 06m
1 stop
Depart: Sun Apr 19 2015 Return: Sun Apr 26 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
ORL
9:00a
MDW
2:45p
5h 45m
1 stop
MDW
2:35p
ORL
7:13a
40h 38m
1 stop
Change your search
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
137 7:15 am 9:15 am Jan 5 - Jan 5
244 7:15 am 9:15 am Dec 29 - Jan 4
963 7:15 am 9:15 am Jan 1 - Jan 1
2647 7:20 am 9:10 am Dec 28 - Dec 28
1621 8:00 am 9:55 am Jan 12 - Mar 6
1621 8:00 am 9:55 am Jan 7 - Jan 9
3421 8:45 am 10:40 am Jan 10 - Feb 28
139 9:00 am 10:55 am Jan 6 - Mar 6
1986 9:20 am 11:10 am Dec 26 - Dec 28
1849 9:25 am 11:15 am Dec 29 - Jan 5
4877 10:25 am 12:25 pm Dec 31 - Dec 31
979 11:00 am 12:50 pm Jan 11 - Mar 1
979 11:00 am 12:50 pm Jan 6 - Mar 6
2464 11:20 am 1:10 pm Jan 10 - Feb 28
1253 12:05 pm 1:55 pm Jan 4 - Jan 4
1253 12:05 pm 1:55 pm Jan 3 - Jan 3
277 12:05 pm 1:55 pm Jan 1 - Jan 1
277 12:05 pm 1:55 pm Dec 29 - Jan 5
1560 12:30 pm 2:20 pm Dec 28 - Dec 28
3332 1:45 pm 3:35 pm Dec 31 - Dec 31
538 2:00 pm 3:50 pm Jan 26 - Mar 6
538 2:00 pm 3:50 pm Jan 6 - Jan 23
538 2:00 pm 3:50 pm Jan 11 - Jan 25
3113 2:10 pm 4:00 pm Jan 10 - Feb 21
4136 2:20 pm 4:10 pm Dec 28 - Dec 28
939 3:10 pm 5:00 pm Dec 28 - Dec 28
555 3:25 pm 5:15 pm Jan 25 - Jan 28
555 3:25 pm 5:15 pm Jan 6 - Jan 23
683 3:35 pm 5:30 pm Jan 5 - Jan 5
683 3:35 pm 5:30 pm Dec 29 - Jan 2
1341 3:40 pm 5:35 pm Jan 1 - Jan 1
2264 3:40 pm 5:35 pm Jan 3 - Jan 3
2264 3:40 pm 5:35 pm Jan 4 - Jan 4
604 4:25 pm 6:15 pm Jan 5 - Jan 5
671 4:25 pm 6:15 pm Dec 26 - Dec 28
3699 4:30 pm 6:20 pm Jan 10 - Feb 28
1139 4:35 pm 6:25 pm Jan 3 - Jan 3
2024 4:35 pm 6:25 pm Dec 29 - Jan 2
412 4:35 pm 6:25 pm Jan 4 - Jan 4
871 5:05 pm 7:00 pm Jan 6 - Mar 6
871 5:05 pm 7:00 pm Jan 11 - Mar 1
2896 5:55 pm 7:50 pm Dec 31 - Dec 31
3600 6:10 pm 8:05 pm Jan 10 - Feb 28
3887 7:00 pm 8:50 pm Jan 10 - Feb 28
127 7:05 pm 8:55 pm Jan 5 - Jan 5
127 7:05 pm 8:55 pm Dec 29 - Jan 4
127 7:05 pm 8:55 pm Dec 31 - Dec 31
1827 7:30 pm 9:20 pm Dec 28 - Dec 28
3931 7:50 pm 9:40 pm Jan 6 - Mar 6
521 8:05 pm 9:55 pm Jan 1 - Jan 1
521 8:05 pm 9:55 pm Dec 31 - Dec 31
2151 9:00 pm 10:50 pm Dec 29 - Jan 4
3790 9:00 pm 10:50 pm Jan 10 - Feb 28
491 9:10 pm 11:00 pm Jan 5 - Jan 5
1186 9:15 pm 11:05 pm Dec 26 - Dec 28
2655 9:30 pm 11:20 pm Dec 31 - Dec 31
1622 9:50 pm 11:40 pm Jan 1 - Jan 1
470 10:00 pm 11:50 pm Dec 29 - Jan 5
Airports
Origin

Orlando
$272
Destination

Chicago
$272