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

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 Chicago Midway to Orlando

(Round-trip)
Depart: Wed Dec 14 2016 Return: Sun Dec 18 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
12:00a
MCO
12:58a
0h 58m
nonstop
MCO
8:00a
MDW
10:58a
2h 58m
nonstop
Depart: Thu Dec 15 2016 Return: Fri Dec 16 2016 Trip spans 2 days
Delta
Delta
MDW
1:30a
MCO
7:17a
5h 47m
1 stop
MCO
2:50a
MDW
7:43a
4h 53m
1 stop
Depart: Mon Dec 19 2016 Return: Sat Dec 24 2016 Trip spans 6 days
Delta
Delta
MDW
10:16a
MCO
4:27p
6h 11m
1 stop
MCO
12:30p
MDW
6:20p
5h 50m
1 stop
Depart: Wed Jan 4 2017 Return: Tue Jan 10 2017 Trip spans 7 days
Delta
Delta
MDW
12:59p
MCO
6:05p
5h 06m
1 stop
MCO
4:20a
MDW
10:54a
6h 34m
1 stop
Depart: Thu Jan 5 2017 Return: Wed Jan 11 2017 Trip spans 7 days
Delta
Delta
MDW
12:59p
MCO
6:05p
5h 06m
1 stop
MCO
3:25a
MDW
7:45a
4h 20m
1 stop
Depart: Fri Jan 6 2017 Return: Wed Jan 11 2017 Trip spans 6 days
Delta
Delta
MDW
12:59p
MCO
6:05p
5h 06m
1 stop
MCO
3:25a
MDW
7:45a
4h 20m
1 stop
Depart: Sat Jan 7 2017 Return: Mon Jan 9 2017 Trip spans 3 days
Delta
Delta
MDW
11:50a
MCO
5:18p
5h 28m
1 stop
MCO
2:00a
MDW
10:58a
8h 58m
1 stop
Depart: Sun Jan 8 2017 Return: Tue Jan 10 2017 Trip spans 3 days
Delta
Delta
MDW
10:29a
MCO
4:45p
6h 16m
1 stop
MCO
4:20a
MDW
10:54a
6h 34m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Delta
Delta
MDW
11:50a
MCO
4:51p
5h 01m
1 stop
MCO
12:20a
MDW
5:55a
5h 35m
1 stop
Depart: Sat Apr 1 2017 Return: Sat Apr 8 2017 Trip spans 8 days
Major Airline
Major Airline
MDW
2:00a
MCO
2:58a
0h 58m
nonstop
MCO
2:00a
MDW
4:58a
2h 58m
nonstop
Depart: Tue Jan 10 2017 Return: Thu Jan 12 2017 Trip spans 3 days
Delta
Delta
MDW
11:50a
MCO
4:51p
5h 01m
1 stop
MCO
3:36a
MDW
8:34a
4h 58m
1 stop
Depart: Wed Jan 11 2017 Return: Thu Jan 12 2017 Trip spans 2 days
Delta
Delta
MDW
4:15a
MCO
9:23a
5h 08m
1 stop
MCO
1:30a
MDW
5:55a
4h 25m
1 stop
Depart: Sat Jan 14 2017 Return: Tue Jan 17 2017 Trip spans 4 days
Delta
Delta
MDW
11:50a
MCO
5:18p
5h 28m
1 stop
MCO
12:20a
MDW
5:55a
5h 35m
1 stop
Depart: Sun Jan 15 2017 Return: Tue Jan 17 2017 Trip spans 3 days
Delta
Delta
MDW
7:20a
MCO
11:20a
4h 00m
1 stop
MCO
12:20a
MDW
5:55a
5h 35m
1 stop
Depart: Mon Jan 16 2017 Return: Tue Jan 17 2017 Trip spans 2 days
Delta
Delta
MDW
11:50a
MCO
4:51p
5h 01m
1 stop
MCO
1:25p
MDW
6:46p
5h 21m
1 stop
Depart: Tue Jan 17 2017 Return: Wed Jan 18 2017 Trip spans 2 days
Delta
Delta
MDW
7:20a
MCO
11:21a
4h 01m
1 stop
MCO
3:25a
MDW
7:45a
4h 20m
1 stop
Depart: Wed Jan 18 2017 Return: Thu Jan 19 2017 Trip spans 2 days
Delta
Delta
MDW
7:20a
MCO
11:21a
4h 01m
1 stop
MCO
5:20a
MDW
9:33a
4h 13m
1 stop
Depart: Thu Jan 19 2017 Return: Fri Jan 20 2017 Trip spans 2 days
Delta
Delta
MDW
7:20a
MCO
2:28p
7h 08m
1 stop
MCO
6:20a
MDW
12:11p
5h 51m
1 stop
Depart: Fri Jan 20 2017 Return: Sat Jan 21 2017 Trip spans 2 days
Delta
Delta
MDW
1:00a
MCO
5:27a
4h 27m
1 stop
MCO
1:00a
MDW
5:40a
4h 40m
1 stop
Depart: Sat Jan 21 2017 Return: Wed Jan 25 2017 Trip spans 5 days
Delta
Delta
MDW
8:45a
MCO
2:26p
5h 41m
1 stop
MCO
12:30p
MDW
6:46p
6h 16m
1 stop
Select an airline:  Southwest
Direct flights MDW to ORL on Southwest
Flight # Depart MDW Arrive MCO Sun Mon Tue Wed Thu Fri Sat Valid Between
6566 5:40 am 9:30 am Dec 25 - Dec 25
2631 5:45 am 9:20 am Jan 7 - Mar 4
661 5:45 am 9:20 am Jan 6 - Feb 13
661 5:45 am 9:20 am Jan 8 - Jan 29
661 5:50 am 9:25 am Jan 5 - Jan 5
6888 5:50 am 9:30 am Jan 1 - Jan 4
6888 5:50 am 9:30 am Dec 18 - Dec 20
6611 5:55 am 9:35 am Dec 31 - Dec 31
6583 6:25 am 10:05 am Dec 17 - Dec 17
2105 6:45 am 10:20 am Jan 7 - Mar 4
6221 7:00 am 10:40 am Dec 21 - Jan 2
2329 7:10 am 10:50 am Dec 31 - Dec 31
1094 7:20 am 11:00 am Jan 3 - Jan 4
1094 7:20 am 11:00 am Dec 8 - Dec 20
1585 7:20 am 10:55 am Jan 5 - Feb 13
2250 7:20 am 11:00 am Dec 25 - Dec 25
6395 7:20 am 11:00 am Dec 11 - Dec 18
6395 7:20 am 11:00 am Jan 1 - Jan 1
4129 7:30 am 11:10 am Dec 24 - Dec 24
1434 7:35 am 11:15 am Dec 17 - Dec 17
2348 7:45 am 11:15 am Jan 7 - Feb 18
2348 7:45 am 11:15 am Jan 8 - Feb 12
1709 8:25 am 12:00 pm Jan 5 - Mar 8
1864 8:25 am 12:00 pm Dec 24 - Dec 24
3224 8:25 am 12:00 pm Dec 31 - Dec 31
1301 8:45 am 12:20 pm Dec 17 - Dec 17
5474 8:45 am 12:20 pm Jan 7 - Mar 4
2138 9:00 am 12:40 pm Jan 15 - Jan 29
2138 9:00 am 12:40 pm Jan 8 - Jan 8
1716 9:20 am 1:00 pm Dec 24 - Dec 24
345 9:20 am 1:00 pm Dec 8 - Dec 20
345 9:20 am 1:00 pm Jan 1 - Jan 4
361 9:20 am 1:00 pm Dec 25 - Dec 25
1978 9:25 am 1:00 pm Dec 31 - Dec 31
4253 9:45 am 1:20 pm Dec 21 - Jan 2
1582 10:15 am 1:50 pm Dec 17 - Dec 17
2252 11:35 am 3:10 pm Dec 25 - Dec 25
621 11:35 am 3:10 pm Dec 11 - Dec 18
621 11:35 am 3:10 pm Dec 8 - Dec 20
621 11:35 am 3:10 pm Jan 3 - Jan 4
621 11:35 am 3:10 pm Jan 1 - Jan 1
1599 11:45 am 3:20 pm Dec 21 - Jan 2
1588 12:35 pm 4:10 pm Dec 17 - Dec 17
3974 12:35 pm 4:10 pm Dec 24 - Dec 24
1758 12:40 pm 4:15 pm Dec 31 - Dec 31
3269 12:40 pm 4:15 pm Dec 21 - Jan 2
960 1:00 pm 4:30 pm Jan 7 - Mar 4
1464 1:20 pm 4:50 pm Jan 5 - Mar 8
4053 1:25 pm 5:00 pm Jan 8 - Jan 22
2649 1:30 pm 5:10 pm Dec 24 - Dec 24
60 1:30 pm 5:10 pm Dec 31 - Dec 31
5054 2:45 pm 6:15 pm Jan 7 - Mar 4
137 3:00 pm 6:35 pm Dec 21 - Jan 2
137 3:00 pm 6:35 pm Dec 25 - Dec 25
3455 3:00 pm 6:35 pm Dec 8 - Dec 20
3455 3:00 pm 6:35 pm Jan 1 - Jan 1
3455 3:00 pm 6:35 pm Jan 3 - Jan 4
3455 3:00 pm 6:35 pm Dec 11 - Dec 18
5433 3:35 pm 7:10 pm Dec 17 - Dec 17
1098 3:40 pm 7:15 pm Dec 24 - Dec 24
5788 3:40 pm 7:15 pm Dec 31 - Dec 31
3068 4:10 pm 7:40 pm Jan 8 - Jan 29
248 4:20 pm 7:50 pm Jan 5 - Feb 13
6141 4:20 pm 7:55 pm Dec 21 - Jan 2
3144 4:30 pm 8:05 pm Jan 3 - Jan 4
3144 4:30 pm 8:05 pm Dec 8 - Dec 20
4202 4:30 pm 8:05 pm Jan 1 - Jan 1
4202 4:30 pm 8:05 pm Dec 18 - Dec 18
5495 4:30 pm 8:00 pm Jan 7 - Mar 4
955 5:05 pm 8:40 pm Dec 25 - Dec 25
1729 5:10 pm 8:45 pm Dec 17 - Dec 17
4365 5:20 pm 8:55 pm Dec 21 - Jan 2
794 5:30 pm 9:00 pm Jan 5 - Feb 13
1111 5:55 pm 9:30 pm Dec 24 - Dec 24
1446 6:10 pm 9:45 pm Dec 31 - Dec 31
604 6:40 pm 10:15 pm Jan 5 - Feb 13
3510 6:55 pm 10:25 pm Jan 8 - Jan 8
1408 7:10 pm 10:45 pm Dec 25 - Dec 25
282 7:10 pm 10:45 pm Jan 1 - Jan 4
282 7:10 pm 10:45 pm Dec 8 - Dec 20
1379 7:25 pm 11:00 pm Dec 17 - Dec 17
3094 7:30 pm 11:00 pm Jan 15 - Jan 29
1514 8:15 pm 11:55 pm Jan 1 - Jan 3
1514 8:15 pm 11:55 pm Dec 18 - Dec 20
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$203
Destination

Orlando
$203
Airlines