Find Deals on Flights from Orlando to Chicago Midway (ORL - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Fri Dec 16 2016 Return: Sun Dec 18 2016 Trip spans 3 days
Major Airline
Major Airline
MCO
12:00a
MDW
2:58a
2h 58m
nonstop
MDW
8:00a
MCO
8:58a
0h 58m
nonstop
Depart: Mon Dec 12 2016 Return: Tue Dec 13 2016 Trip spans 2 days
Delta
Delta
MCO
9:22a
MDW
3:09p
5h 47m
1 stop
MDW
8:59a
MCO
2:48p
5h 49m
1 stop
Depart: Tue Dec 13 2016 Return: Wed Dec 14 2016 Trip spans 2 days
Delta
Delta
MCO
8:25a
MDW
1:23p
4h 58m
1 stop
MDW
2:00a
MCO
7:04a
5h 04m
1 stop
Depart: Thu Dec 15 2016 Return: Tue Dec 20 2016 Trip spans 6 days
Delta
Delta
MCO
9:19a
MDW
4:40p
7h 21m
1 stop
MDW
4:18a
MCO
9:09a
4h 51m
1 stop
Depart: Sat Dec 17 2016 Return: Sun Dec 18 2016 Trip spans 2 days
Delta
Delta
MCO
12:30p
MDW
6:21p
5h 51m
1 stop
MDW
4:18a
MCO
9:09a
4h 51m
1 stop
Depart: Sun Dec 18 2016 Return: Tue Dec 20 2016 Trip spans 3 days
Delta
Delta
MCO
11:14a
MDW
4:39p
5h 25m
1 stop
MDW
4:18a
MCO
9:09a
4h 51m
1 stop
Depart: Mon Dec 19 2016 Return: Tue Dec 20 2016 Trip spans 2 days
Delta
Delta
MCO
2:30a
MDW
7:45a
5h 15m
1 stop
MDW
4:18a
MCO
9:09a
4h 51m
1 stop
Depart: Mon Jan 9 2017 Return: Sat Jan 14 2017 Trip spans 6 days
Delta
Delta
MCO
4:20a
MDW
12:51p
8h 31m
1 stop
MDW
11:50a
MCO
5:18p
5h 28m
1 stop
Depart: Tue Jan 10 2017 Return: Sat Jan 14 2017 Trip spans 5 days
Delta
Delta
MCO
1:30a
MDW
5:55a
4h 25m
1 stop
MDW
8:45a
MCO
1:31p
4h 46m
1 stop
Depart: Wed Jan 11 2017 Return: Sat Jan 14 2017 Trip spans 4 days
Delta
Delta
MCO
2:30a
MDW
7:45a
5h 15m
1 stop
MDW
12:00p
MCO
5:21p
5h 21m
1 stop
Depart: Thu Jan 12 2017 Return: Sat Jan 14 2017 Trip spans 3 days
Delta
Delta
MCO
4:20a
MDW
10:54a
6h 34m
1 stop
MDW
8:45a
MCO
1:31p
4h 46m
1 stop
Depart: Sat Jan 14 2017 Return: Sun Jan 15 2017 Trip spans 2 days
Delta
Delta
MCO
4:20a
MDW
11:01a
6h 41m
1 stop
MDW
7:20a
MCO
12:24p
5h 04m
1 stop
Depart: Sun Jan 15 2017 Return: Mon Jan 16 2017 Trip spans 2 days
Delta
Delta
MCO
12:20a
MDW
6:04a
5h 44m
1 stop
MDW
12:59p
MCO
6:42p
5h 43m
1 stop
Depart: Tue Jan 17 2017 Return: Thu Jan 19 2017 Trip spans 3 days
Delta
Delta
MCO
2:25p
MDW
6:46p
4h 21m
1 stop
MDW
2:10a
MCO
7:20a
5h 10m
1 stop
Depart: Wed Jan 18 2017 Return: Thu Jan 19 2017 Trip spans 2 days
Delta
Delta
MCO
3:25a
MDW
7:45a
4h 20m
1 stop
MDW
7:20a
MCO
12:25p
5h 05m
1 stop
Depart: Thu Jan 19 2017 Return: Fri Jan 20 2017 Trip spans 2 days
Delta
Delta
MCO
2:25p
MDW
6:46p
4h 21m
1 stop
MDW
12:59p
MCO
6:42p
5h 43m
1 stop
Depart: Fri Jan 20 2017 Return: Sat Jan 21 2017 Trip spans 2 days
Delta
Delta
MCO
3:36a
MDW
8:34a
4h 58m
1 stop
MDW
2:10a
MCO
8:22a
6h 12m
1 stop
Depart: Sat Jan 21 2017 Return: Sun Jan 22 2017 Trip spans 2 days
Delta
Delta
MCO
3:25a
MDW
9:01a
5h 36m
1 stop
MDW
7:32a
MCO
2:30p
6h 58m
1 stop
Depart: Tue Jan 24 2017 Return: Fri Jan 27 2017 Trip spans 4 days
Delta
Delta
MCO
2:30a
MDW
7:45a
5h 15m
1 stop
MDW
10:40a
MCO
3:34p
4h 54m
1 stop
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Delta
Delta
MCO
5:20a
MDW
9:33a
4h 13m
1 stop
MDW
5:30a
MCO
10:25a
4h 55m
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
2270 6:05 am 7:55 am Dec 15 - Dec 16
2270 6:05 am 7:55 am Dec 18 - Dec 20
2270 6:05 am 7:55 am Jan 1 - Jan 3
5651 6:05 am 7:55 am Dec 1 - Dec 14
5651 6:05 am 7:55 am Jan 4 - Jan 4
2024 6:45 am 8:35 am Dec 17 - Dec 17
6199 7:20 am 9:10 am Dec 21 - Jan 2
2265 7:35 am 9:25 am Dec 1 - Dec 20
2265 7:35 am 9:25 am Jan 3 - Jan 4
1140 8:05 am 9:55 am Jan 1 - Jan 1
1140 8:05 am 9:55 am Dec 4 - Dec 18
1842 8:05 am 9:55 am Dec 25 - Dec 25
6202 8:45 am 10:35 am Dec 21 - Jan 2
4693 9:00 am 10:50 am Jan 5 - Feb 13
1156 9:05 am 10:55 am Dec 17 - Dec 17
2885 9:30 am 11:20 am Dec 31 - Dec 31
338 9:35 am 11:20 am Dec 24 - Dec 24
4918 9:45 am 11:35 am Jan 8 - Jan 29
4349 10:45 am 12:30 pm Dec 21 - Jan 2
1108 10:50 am 12:40 pm Jan 5 - Jan 13
2314 11:05 am 12:55 pm Dec 1 - Dec 20
2314 11:05 am 12:55 pm Jan 1 - Jan 4
3248 11:10 am 1:00 pm Dec 25 - Dec 25
1803 11:20 am 1:05 pm Dec 24 - Dec 24
6616 11:20 am 1:05 pm Dec 31 - Dec 31
2566 11:25 am 1:15 pm Jan 7 - Mar 4
4480 11:40 am 1:35 pm Jan 8 - Jan 29
4695 12:05 pm 2:00 pm Jan 5 - Feb 13
5234 12:05 pm 1:50 pm Dec 21 - Jan 2
3429 12:15 pm 2:00 pm Jan 3 - Jan 4
3429 12:15 pm 2:00 pm Jan 1 - Jan 1
3429 12:15 pm 2:00 pm Dec 4 - Dec 18
3429 12:15 pm 2:00 pm Dec 1 - Dec 20
3263 12:20 pm 2:05 pm Dec 25 - Dec 25
2072 12:45 pm 2:30 pm Dec 31 - Dec 31
1865 12:50 pm 2:35 pm Dec 17 - Dec 17
1080 2:05 pm 3:55 pm Dec 24 - Dec 24
1939 2:05 pm 3:55 pm Dec 31 - Dec 31
1310 2:15 pm 4:05 pm Dec 17 - Dec 17
5892 2:30 pm 4:25 pm Jan 7 - Mar 4
3059 3:05 pm 5:00 pm Jan 8 - Jan 29
3562 3:10 pm 5:00 pm Dec 21 - Jan 2
1166 3:40 pm 5:30 pm Dec 25 - Dec 25
538 3:55 pm 5:45 pm Jan 1 - Jan 4
538 3:55 pm 5:45 pm Dec 1 - Dec 20
1223 4:00 pm 5:50 pm Dec 17 - Dec 17
2342 4:15 pm 6:05 pm Dec 31 - Dec 31
3127 4:15 pm 6:05 pm Dec 24 - Dec 24
1465 4:35 pm 6:30 pm Jan 8 - Jan 29
1465 4:35 pm 6:30 pm Jan 7 - Mar 4
1834 4:40 pm 6:30 pm Jan 6 - Mar 8
2199 4:40 pm 6:30 pm Dec 25 - Dec 25
642 4:40 pm 6:30 pm Jan 1 - Jan 4
642 4:40 pm 6:30 pm Dec 1 - Dec 20
231 4:50 pm 6:35 pm Jan 5 - Jan 5
1233 5:10 pm 7:00 pm Dec 31 - Dec 31
2446 5:10 pm 7:00 pm Dec 24 - Dec 24
2246 5:25 pm 7:15 pm Dec 21 - Jan 2
2509 5:40 pm 7:35 pm Jan 7 - Mar 4
529 5:45 pm 7:35 pm Jan 5 - Feb 13
4649 6:30 pm 8:20 pm Jan 8 - Jan 29
1102 7:10 pm 9:00 pm Jan 7 - Mar 4
1383 7:10 pm 8:55 pm Dec 25 - Dec 25
5150 7:15 pm 9:00 pm Dec 17 - Dec 17
1302 7:30 pm 9:15 pm Dec 24 - Dec 24
4316 7:30 pm 9:20 pm Jan 5 - Feb 13
6396 7:30 pm 9:15 pm Dec 31 - Dec 31
5728 7:55 pm 9:40 pm Dec 21 - Jan 2
6801 8:00 pm 9:45 pm Dec 31 - Dec 31
2458 8:15 pm 10:05 pm Jan 7 - Jan 14
3125 8:15 pm 10:00 pm Jan 1 - Jan 4
3125 8:15 pm 10:00 pm Dec 1 - Dec 20
3599 8:15 pm 10:00 pm Dec 25 - Dec 25
4679 8:30 pm 10:20 pm Jan 5 - Jan 5
4679 8:35 pm 10:25 pm Jan 6 - Feb 17
3229 8:45 pm 10:35 pm Jan 8 - Jan 29
1851 9:00 pm 10:45 pm Dec 24 - Dec 24
5727 9:15 pm 11:00 pm Dec 17 - Dec 17
39 9:55 pm 11:40 pm Jan 3 - Jan 3
39 9:55 pm 11:40 pm Dec 15 - Dec 20
39 9:55 pm 11:40 pm Jan 1 - Jan 1
39 9:55 pm 11:40 pm Dec 18 - Dec 18
2797 10:15 pm 12:05 am Jan 8 - Jan 29
1251 10:35 pm 12:20 am Dec 17 - Dec 17
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Orlando
$191
Destination

Chicago
$191
Airlines