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
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 Aug 31 2016 Return: Wed Sep 7 2016 Trip spans 8 days
Depart: Wed Sep 7 2016 Return: Fri Sep 9 2016 Trip spans 3 days
Depart: Wed Dec 7 2016 Return: Mon Dec 12 2016 Trip spans 6 days
Depart: Thu Dec 8 2016 Return: Wed Dec 14 2016 Trip spans 7 days
Depart: Thu Sep 8 2016 Return: Sat Sep 10 2016 Trip spans 3 days
Depart: Sat Aug 27 2016 Return: Mon Aug 29 2016 Trip spans 3 days
Depart: Fri Sep 9 2016 Return: Tue Sep 13 2016 Trip spans 5 days
Depart: Tue Oct 11 2016 Return: Thu Oct 13 2016 Trip spans 3 days
Depart: Sat Sep 10 2016 Return: Tue Sep 13 2016 Trip spans 4 days
Depart: Mon Nov 14 2016 Return: Fri Nov 18 2016 Trip spans 5 days
Depart: Mon Sep 12 2016 Return: Tue Sep 20 2016 Trip spans 9 days
Depart: Tue Nov 29 2016 Return: Sun Dec 4 2016 Trip spans 6 days
Depart: Wed Sep 14 2016 Return: Thu Sep 15 2016 Trip spans 2 days
Depart: Mon Dec 12 2016 Return: Fri Dec 16 2016 Trip spans 5 days
Depart: Thu Sep 15 2016 Return: Sun Sep 18 2016 Trip spans 4 days
Depart: Sat Jan 7 2017 Return: Tue Jan 10 2017 Trip spans 4 days
Depart: Tue Sep 20 2016 Return: Wed Sep 21 2016 Trip spans 2 days
Depart: Wed Jan 18 2017 Return: Tue Jan 24 2017 Trip spans 7 days
Depart: Wed Sep 21 2016 Return: Sat Sep 24 2016 Trip spans 4 days
Depart: Tue Sep 13 2016 Return: Wed Sep 14 2016 Trip spans 2 days
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
342 6:30 am 10:00 am Oct 2 - Nov 4
342 6:30 am 10:00 am Aug 23 - Sep 2
342 6:30 am 10:00 am Sep 6 - Sep 30
2532 6:55 am 10:25 am Sep 17 - Nov 5
2532 6:55 am 10:25 am Aug 27 - Sep 10
1719 7:10 am 10:40 am Sep 4 - Sep 4
4477 7:35 am 11:05 am Oct 2 - Oct 30
1989 7:40 am 11:10 am Aug 23 - Sep 2
1989 7:40 am 11:10 am Sep 6 - Sep 30
3574 7:40 am 11:10 am Aug 27 - Oct 1
5484 7:40 am 11:10 am Sep 11 - Sep 25
695 7:40 am 11:10 am Sep 5 - Sep 5
5647 8:35 am 12:10 pm Sep 3 - Sep 3
23 9:10 am 12:45 pm Sep 3 - Sep 3
3417 9:10 am 12:45 pm Sep 10 - Oct 1
1789 10:05 am 1:35 pm Sep 10 - Oct 1
996 10:05 am 1:35 pm Sep 3 - Sep 3
1295 10:20 am 1:50 pm Sep 4 - Sep 5
2730 10:20 am 1:50 pm Sep 6 - Sep 30
2730 10:20 am 1:50 pm Aug 23 - Sep 2
575 10:20 am 1:45 pm Oct 2 - Nov 4
1234 11:20 am 2:50 pm Sep 4 - Sep 5
3091 11:25 am 2:55 pm Sep 6 - Sep 30
3091 11:25 am 2:55 pm Aug 23 - Sep 2
3091 11:30 am 3:00 pm Oct 2 - Nov 4
1253 12:25 pm 4:00 pm Sep 10 - Oct 1
2048 12:25 pm 4:00 pm Sep 3 - Sep 3
1001 1:05 pm 4:40 pm Sep 3 - Sep 3
772 1:10 pm 4:45 pm Sep 10 - Oct 1
5154 1:35 pm 5:10 pm Aug 23 - Sep 2
3730 3:15 pm 6:50 pm Sep 10 - Oct 1
2224 3:35 pm 7:10 pm Sep 4 - Sep 4
3230 3:35 pm 7:10 pm Aug 23 - Sep 2
3230 3:35 pm 7:05 pm Oct 2 - Oct 28
3230 3:35 pm 7:10 pm Sep 5 - Sep 30
2128 4:10 pm 7:50 pm Sep 10 - Oct 1
3778 4:55 pm 8:30 pm Sep 4 - Sep 4
2574 6:05 pm 9:40 pm Sep 10 - Oct 1
2737 6:05 pm 9:40 pm Sep 4 - Sep 5
4009 6:05 pm 9:40 pm Aug 23 - Sep 2
4009 6:05 pm 9:40 pm Sep 6 - Sep 30
411 6:10 pm 9:40 pm Oct 2 - Oct 30
1722 7:05 pm 10:40 pm Sep 5 - Sep 5
2986 7:30 pm 11:05 pm Aug 23 - Sep 2
2986 7:30 pm 11:05 pm Oct 2 - Oct 30
2986 7:30 pm 11:05 pm Sep 9 - Sep 30
2986 7:35 pm 11:15 pm Sep 4 - Sep 4
* 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
$109
Destination

Orlando
$109
Airlines