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Find Flight Deals 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: Tue Apr 14 2015 Return: Mon Apr 20 2015 Trip spans 7 days
Delta
Delta
MCO
4:30a
MDW
8:41a
4h 11m
1 stop
MDW
10:30a
MCO
2:35p
4h 05m
1 stop
Depart: Wed Apr 15 2015 Return: Mon Apr 20 2015 Trip spans 6 days
Delta
Delta
MCO
11:30a
MDW
4:54p
5h 24m
1 stop
MDW
10:30a
MCO
2:35p
4h 05m
1 stop
Depart: Fri Apr 17 2015 Return: Mon Apr 20 2015 Trip spans 4 days
Delta
Delta
MCO
4:30a
MDW
10:55a
6h 25m
1 stop
MDW
7:05a
MCO
12:25p
5h 20m
1 stop
Depart: Tue Apr 21 2015 Return: Sat Apr 25 2015 Trip spans 5 days
Delta
Delta
MCO
4:30a
MDW
8:41a
4h 11m
1 stop
MDW
11:30a
MCO
3:23p
3h 53m
1 stop
Depart: Wed Apr 22 2015 Return: Sat Apr 25 2015 Trip spans 4 days
Delta
Delta
MCO
4:30a
MDW
8:41a
4h 11m
1 stop
MDW
11:30a
MCO
3:23p
3h 53m
1 stop
Depart: Thu Apr 23 2015 Return: Sat Apr 25 2015 Trip spans 3 days
Delta
Delta
MCO
2:20a
MDW
6:24a
4h 04m
1 stop
MDW
11:30a
MCO
3:23p
3h 53m
1 stop
Depart: Fri Apr 24 2015 Return: Sat Apr 25 2015 Trip spans 2 days
Delta
Delta
MCO
5:20a
MDW
12:25p
7h 05m
1 stop
MDW
8:15a
MCO
12:23p
4h 08m
1 stop
Depart: Sat Apr 25 2015 Return: Sun Apr 26 2015 Trip spans 2 days
Delta
Delta
MCO
4:30a
MDW
8:40a
4h 10m
1 stop
MDW
10:30a
MCO
2:35p
4h 05m
1 stop
Depart: Sun Apr 26 2015 Return: Mon Apr 27 2015 Trip spans 2 days
Delta
Delta
MCO
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
2:00a
MCO
6:22a
4h 22m
1 stop
Depart: Mon Apr 27 2015 Return: Tue Apr 28 2015 Trip spans 2 days
Delta
Delta
MCO
2:30p
MDW
7:09p
4h 39m
1 stop
MDW
5:50a
MCO
10:29a
4h 39m
1 stop
Depart: Wed Apr 29 2015 Return: Mon May 4 2015 Trip spans 6 days
Delta
Delta
MCO
2:30p
MDW
7:09p
4h 39m
1 stop
MDW
3:15a
MCO
8:18a
5h 03m
1 stop
Depart: Thu Apr 30 2015 Return: Mon May 4 2015 Trip spans 5 days
Delta
Delta
MCO
1:20a
MDW
6:15a
4h 55m
1 stop
MDW
9:50a
MCO
2:22p
4h 32m
1 stop
Depart: Fri May 1 2015 Return: Sat May 2 2015 Trip spans 2 days
Delta
Delta
MCO
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
11:30a
MCO
4:34p
5h 04m
1 stop
Depart: Sat May 2 2015 Return: Mon May 4 2015 Trip spans 3 days
Delta
Delta
MCO
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
9:50a
MCO
2:22p
4h 32m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
MCO
1:30p
MDW
6:32p
5h 02m
1 stop
MDW
9:50a
MCO
2:22p
4h 32m
1 stop
Depart: Wed May 6 2015 Return: Mon May 11 2015 Trip spans 6 days
Delta
Delta
MCO
5:30a
MDW
10:12a
4h 42m
1 stop
MDW
8:40a
MCO
1:11p
4h 31m
1 stop
Depart: Thu May 7 2015 Return: Mon May 11 2015 Trip spans 5 days
Delta
Delta
MCO
1:20a
MDW
6:04a
4h 44m
1 stop
MDW
11:27a
MCO
4:34p
5h 07m
1 stop
Depart: Fri May 8 2015 Return: Mon May 11 2015 Trip spans 4 days
Delta
Delta
MCO
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
3:15a
MCO
9:22a
6h 07m
1 stop
Depart: Wed May 13 2015 Return: Sat May 16 2015 Trip spans 4 days
Delta
Delta
MCO
11:30a
MDW
4:54p
5h 24m
1 stop
MDW
8:15a
MCO
2:22p
6h 07m
1 stop
Depart: Thu May 14 2015 Return: Sun May 17 2015 Trip spans 4 days
Delta
Delta
MCO
4:30a
MDW
8:49a
4h 19m
1 stop
MDW
2:00a
MCO
8:22a
6h 22m
1 stop
Change your search
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
1624 6:50 am 8:55 am Mar 7 - Mar 7
1624 6:50 am 8:55 am Mar 14 - Apr 4
581 6:55 am 9:00 am Mar 8 - Apr 6
2442 7:20 am 9:10 am Mar 14 - Apr 4
2442 7:20 am 9:10 am Mar 7 - Mar 7
1621 8:00 am 9:55 am Feb 26 - Mar 6
139 9:00 am 10:55 am Feb 26 - Mar 6
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
114 9:40 am 11:30 am Mar 7 - Mar 7
968 9:55 am 11:45 am Mar 14 - Mar 28
968 9:55 am 11:45 am Apr 4 - Apr 4
4316 10:20 am 12:15 pm Mar 8 - Apr 5
512 10:25 am 12:20 pm Mar 9 - Mar 27
512 10:35 am 12:30 pm Mar 30 - Apr 6
2501 10:55 am 12:50 pm Mar 14 - Apr 4
4855 10:55 am 12:50 pm Mar 7 - Mar 7
979 11:00 am 12:50 pm Feb 26 - Mar 6
2497 11:45 am 1:40 pm Mar 14 - Apr 4
493 11:45 am 1:40 pm Mar 7 - Mar 7
328 11:55 am 1:45 pm Mar 8 - Apr 6
1957 1:10 pm 3:00 pm Mar 7 - Mar 7
1957 1:10 pm 3:00 pm Mar 14 - Apr 4
4124 1:55 pm 3:45 pm Mar 8 - Apr 5
638 1:55 pm 3:45 pm Mar 9 - Apr 6
538 2:00 pm 3:50 pm Mar 2 - Mar 6
181 2:05 pm 3:55 pm Mar 7 - Mar 7
1287 2:10 pm 4:00 pm Mar 14 - Apr 4
223 3:20 pm 5:10 pm Mar 7 - Mar 7
2446 3:20 pm 5:10 pm Mar 14 - Apr 4
555 3:25 pm 5:15 pm Mar 1 - Mar 6
2270 4:10 pm 6:00 pm Mar 14 - Apr 4
1273 4:20 pm 6:10 pm Mar 7 - Mar 7
2330 4:35 pm 6:25 pm Mar 8 - Apr 6
284 5:00 pm 6:50 pm Mar 7 - Mar 7
973 5:00 pm 6:50 pm Mar 14 - Apr 4
871 5:05 pm 7:00 pm Feb 26 - Mar 6
646 5:25 pm 7:15 pm Mar 8 - Apr 6
824 6:05 pm 7:55 pm Mar 8 - Apr 6
185 6:25 pm 8:15 pm Mar 7 - Mar 7
2282 6:25 pm 8:15 pm Mar 14 - Apr 4
2637 7:00 pm 8:55 pm Mar 14 - Apr 4
419 7:00 pm 8:55 pm Mar 7 - Mar 7
3931 7:50 pm 9:40 pm Feb 26 - Mar 6
1386 10:00 pm 11:50 pm Mar 7 - Mar 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
Airlines