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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: 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: Thu Apr 16 2015 Return: Sat Apr 18 2015 Trip spans 3 days
Delta
Delta
MCO
4:30a
MDW
10:55a
6h 25m
1 stop
MDW
8:15a
MCO
12:23p
4h 08m
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: Fri Apr 24 2015 Trip spans 2 days
Delta
Delta
MCO
2:20a
MDW
6:24a
4h 04m
1 stop
MDW
12:00p
MCO
4:24p
4h 24m
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
10:30a
MCO
3:25p
4h 55m
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: Tue Apr 28 2015 Return: Sat May 2 2015 Trip spans 5 days
Delta
Delta
MCO
6:10a
MDW
10:55a
4h 45m
1 stop
MDW
1:59p
MCO
6:54p
4h 55m
1 stop
Depart: Wed Apr 29 2015 Return: Sat May 2 2015 Trip spans 4 days
Delta
Delta
MCO
2:30p
MDW
7:09p
4h 39m
1 stop
MDW
1:59p
MCO
6:54p
4h 55m
1 stop
Depart: Thu Apr 30 2015 Return: Mon May 4 2015 Trip spans 5 days
Delta
Delta
MCO
7:20a
MDW
12:25p
5h 05m
1 stop
MDW
12:00p
MCO
4:30p
4h 30m
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: Thu May 7 2015 Trip spans 2 days
Delta
Delta
MCO
2:20a
MDW
6:23a
4h 03m
1 stop
MDW
6:00a
MCO
11:37a
5h 37m
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: Sat May 9 2015 Trip spans 2 days
Delta
Delta
MCO
1:20a
MDW
6:04a
4h 44m
1 stop
MDW
3:05a
MCO
9:22a
6h 17m
1 stop
Depart: Tue May 12 2015 Return: Tue May 26 2015 Trip spans 15 days
Delta
Delta
MCO
12:20p
MDW
4:58p
4h 38m
1 stop
MDW
12:00p
MCO
4:30p
4h 30m
1 stop
Depart: Fri Apr 10 2015 Return: Fri Apr 17 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MCO
4:45p
MDW
6:40a
61h 55m
1 stop
MDW
6:30a
MCO
2:58p
8h 28m
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 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
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 8 - Mar 13
3834 9:10 am 11:00 am Mar 15 - Mar 20
3834 9:10 am 11:00 am Mar 22 - Apr 6
968 9:55 am 11:45 am Apr 4 - Apr 4
968 9:55 am 11:45 am Mar 14 - Mar 28
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
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
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
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
973 5:00 pm 6:50 pm Mar 14 - Apr 4
321 5:10 pm 6:55 pm Apr 8 - May 22
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
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
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 16 - Apr 6
388 10:05 pm 11:55 pm Mar 8 - Mar 15
4183 10:15 pm 12:05 am Mar 14 - Apr 4
Airports
Origin

Orlando
$250
Destination

Chicago
$250