Find Cheap Flights from Chicago Midway to Orlando (MDW - MCO)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Orlando

(Round-trip)
Depart: Wed May 10 2017 Return: Wed May 17 2017 Trip spans 8 days
Delta
Delta
MDW
5:16a
MCO
12:49p
7h 33m
1 stop
MCO
8:15a
MDW
1:19p
5h 04m
1 stop
Depart: Mon May 15 2017 Return: Tue May 16 2017 Trip spans 2 days
Delta
Delta
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
MCO
11:20a
MDW
5:00p
5h 40m
1 stop
Depart: Fri May 19 2017 Return: Tue May 23 2017 Trip spans 5 days
Delta
Delta
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
MCO
12:25p
MDW
5:00p
4h 35m
1 stop
Depart: Mon May 22 2017 Return: Tue May 23 2017 Trip spans 2 days
Delta
Delta
MDW
5:16a
MCO
10:03a
4h 47m
1 stop
MCO
8:25a
MDW
2:17p
5h 52m
1 stop
Depart: Tue May 30 2017 Return: Sun Jun 4 2017 Trip spans 6 days
Delta
Delta
MDW
11:55a
MCO
4:29p
4h 34m
1 stop
MCO
2:20a
MDW
6:46a
4h 26m
1 stop
Depart: Wed May 31 2017 Return: Sun Jun 4 2017 Trip spans 5 days
Delta
Delta
MDW
1:52p
MCO
6:56p
5h 04m
1 stop
MCO
2:20a
MDW
6:46a
4h 26m
1 stop
Depart: Thu Jun 1 2017 Return: Fri Jun 2 2017 Trip spans 2 days
Delta
Delta
MDW
1:52p
MCO
8:00p
6h 08m
1 stop
MCO
12:14p
MDW
5:35p
5h 21m
1 stop
Depart: Sat Jun 3 2017 Return: Sun Jun 4 2017 Trip spans 2 days
Delta
Delta
MDW
11:55a
MCO
6:55p
7h 00m
1 stop
MCO
3:50a
MDW
8:29a
4h 39m
1 stop
Depart: Mon Jun 5 2017 Return: Tue Jun 6 2017 Trip spans 2 days
Delta
Delta
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
MCO
10:14a
MDW
2:59p
4h 45m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Delta
Delta
MDW
5:16a
MCO
10:03a
4h 47m
1 stop
MCO
10:14a
MDW
2:59p
4h 45m
1 stop
Depart: Wed Jun 7 2017 Return: Fri Jun 9 2017 Trip spans 3 days
Delta
Delta
MDW
5:16a
MCO
12:49p
7h 33m
1 stop
MCO
10:14a
MDW
5:35p
7h 21m
1 stop
Depart: Thu Jun 8 2017 Return: Fri Jun 9 2017 Trip spans 2 days
Delta
Delta
MDW
2:55a
MCO
10:03a
7h 08m
1 stop
MCO
10:14a
MDW
5:35p
7h 21m
1 stop
Depart: Mon Jun 12 2017 Return: Tue Jun 13 2017 Trip spans 2 days
Delta
Delta
MDW
3:53p
MCO
7:59p
4h 06m
1 stop
MCO
9:55a
MDW
3:09p
5h 14m
1 stop
Depart: Tue Jun 13 2017 Return: Wed Jun 14 2017 Trip spans 2 days
Delta
Delta
MDW
3:53p
MCO
7:59p
4h 06m
1 stop
MCO
8:09a
MDW
3:09p
7h 00m
1 stop
Depart: Tue Jul 11 2017 Return: Tue Jul 25 2017 Trip spans 15 days
Delta
Delta
MDW
1:59p
MCO
7:57p
5h 58m
1 stop
MCO
4:25a
MDW
10:07a
5h 42m
1 stop
Depart: Mon Jul 17 2017 Return: Tue Jul 25 2017 Trip spans 9 days
Delta
Delta
MDW
3:20p
MCO
7:57p
4h 37m
1 stop
MCO
1:45p
MDW
7:48p
6h 03m
1 stop
Depart: Tue Jul 25 2017 Return: Wed Aug 2 2017 Trip spans 9 days
Delta
Delta
MDW
3:20p
MCO
7:57p
4h 37m
1 stop
MCO
4:15a
MDW
9:34a
5h 19m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
MDW
3:20p
MCO
7:57p
4h 37m
1 stop
MCO
5:20a
MDW
10:07a
4h 47m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
MDW
1:52p
MCO
6:55p
5h 03m
1 stop
MCO
1:20a
MDW
6:46a
5h 26m
1 stop
Depart: Thu May 25 2017 Return: Thu Jun 1 2017 Trip spans 8 days
Delta
Delta
MDW
2:55a
MCO
10:03a
7h 08m
1 stop
MCO
4:25a
MDW
9:23a
4h 58m
1 stop
Select an airline:  Southwest
Direct flights MDW to MCO on Southwest
Flight # Depart MDW Arrive MCO Sun Mon Tue Wed Thu Fri Sat Valid Between
1625 5:15 am 8:45 am Apr 26 - May 26
1625 5:15 am 8:45 am May 30 - Jun 2
1712 5:20 am 8:50 am Jun 5 - Jun 30
1235 5:30 am 9:00 am Jun 4 - Aug 13
2093 5:40 am 9:10 am Apr 30 - May 21
2093 5:40 am 9:10 am Apr 29 - Jun 3
1301 6:20 am 9:50 am Jun 5 - Aug 14
1998 6:40 am 10:10 am Apr 26 - May 8
1998 6:40 am 10:10 am May 9 - May 26
1998 6:40 am 10:10 am May 30 - Jun 2
4404 6:50 am 10:20 am Apr 29 - Jun 3
471 7:00 am 10:35 am May 29 - May 29
311 7:10 am 10:45 am Jun 5 - Jul 3
4521 7:30 am 11:05 am Apr 30 - May 21
1521 7:35 am 11:05 am Jun 4 - Aug 13
375 7:35 am 11:05 am May 28 - May 28
4394 7:40 am 11:15 am Apr 29 - Jun 3
4521 8:50 am 12:30 pm May 28 - May 28
4505 9:40 am 1:15 pm May 6 - Jun 3
5170 9:40 am 1:10 pm Jun 4 - Aug 13
3611 9:55 am 1:30 pm Jun 5 - Aug 14
2031 10:45 am 2:20 pm Jun 3 - Jun 3
2031 10:55 am 2:30 pm May 6 - May 27
854 11:05 am 2:40 pm May 30 - Jun 2
854 11:05 am 2:40 pm Apr 26 - May 26
157 11:10 am 2:45 pm May 29 - May 29
5014 11:20 am 2:55 pm Jun 4 - Aug 13
5656 11:40 am 3:15 pm Apr 29 - Jun 3
3026 12:00 pm 3:35 pm Apr 30 - May 21
3026 12:10 pm 3:45 pm May 28 - May 28
1966 1:15 pm 4:50 pm Apr 26 - May 8
1966 1:15 pm 4:50 pm May 9 - Jun 2
4403 1:30 pm 5:10 pm Jun 4 - Aug 13
2183 1:40 pm 5:20 pm Jun 5 - Jun 16
5114 2:05 pm 5:45 pm Jun 3 - Jun 3
5578 2:05 pm 5:45 pm May 13 - May 27
5578 2:05 pm 5:45 pm Apr 29 - May 6
2941 2:50 pm 6:25 pm May 28 - May 28
2941 2:50 pm 6:25 pm Apr 30 - May 21
1928 3:00 pm 6:40 pm Jun 4 - Aug 13
4398 3:05 pm 6:40 pm Apr 29 - May 27
4398 3:05 pm 6:40 pm Jun 3 - Jun 3
169 4:15 pm 7:50 pm Apr 26 - May 8
169 4:15 pm 7:50 pm May 9 - Jun 2
5356 5:15 pm 8:50 pm Jun 4 - Aug 13
3372 5:20 pm 8:55 pm Apr 30 - May 28
777 5:40 pm 9:15 pm Apr 29 - Jun 3
5652 5:45 pm 9:20 pm Jun 5 - Jun 30
3422 6:15 pm 9:50 pm May 30 - Jun 2
3422 6:15 pm 9:50 pm Apr 26 - May 26
384 6:45 pm 10:20 pm May 29 - May 29
5033 6:45 pm 10:15 pm Jun 4 - Aug 13
3075 6:55 pm 10:30 pm Apr 30 - May 28
407 7:30 pm 11:00 pm Jun 5 - Jul 3
1226 8:00 pm 11:35 pm May 29 - May 29
3722 8:30 pm 12:05 am Jun 5 - Jun 30
1643 8:45 pm 12:20 am Jun 4 - Aug 13
4138 9:00 pm 12:35 am May 28 - May 28
3475 9:05 pm 12:40 am Apr 26 - May 5
3475 9:10 pm 12:45 am May 8 - May 26
3475 9:10 pm 12:45 am May 30 - Jun 2
1234 9:15 pm 12:50 am May 7 - May 21
220 9:15 pm 12:45 am Jun 5 - Jun 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$204
Destination

Orlando
$204
Airlines