Find Deals on 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: Thu May 19 2016 Return: Sun May 22 2016 Trip spans 4 days
Southwest
Southwest
MDW
2:10a
MCO
4:50a
2h 40m
nonstop
MCO
3:05a
MDW
5:50a
2h 45m
nonstop
Depart: Wed May 4 2016 Return: Tue May 10 2016 Trip spans 7 days
Delta
Delta
MDW
6:09a
MCO
11:25a
5h 16m
1 stop
MCO
7:30a
MDW
11:59a
4h 29m
1 stop
Depart: Fri Aug 5 2016 Return: Tue Aug 9 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
9:40a
MCO
4:49p
7h 09m
1 stop
MCO
4:20a
MDW
9:23a
5h 03m
1 stop
Depart: Fri May 20 2016 Return: Sun May 22 2016 Trip spans 3 days
Southwest
Southwest
MDW
3:30p
MCO
6:05p
2h 35m
nonstop
MCO
6:00p
MDW
8:40p
2h 40m
nonstop
Depart: Thu May 5 2016 Return: Sat May 7 2016 Trip spans 3 days
Delta
Delta
MDW
7:02a
MCO
12:44p
5h 42m
1 stop
MCO
1:30p
MDW
7:34p
6h 04m
1 stop
Depart: Thu Jun 2 2016 Return: Tue Jun 7 2016 Trip spans 6 days
Southwest
Southwest
MDW
3:00a
MCO
9:40a
6h 40m
1 stop
MCO
6:30p
MDW
9:10p
2h 40m
nonstop
Depart: Sat May 7 2016 Return: Sat May 14 2016 Trip spans 8 days
Delta
Delta
MDW
1:53p
MCO
6:33p
4h 40m
1 stop
MCO
5:30a
MDW
11:57a
6h 27m
1 stop
Depart: Mon May 9 2016 Return: Tue May 10 2016 Trip spans 2 days
Delta
Delta
MDW
9:55a
MCO
2:29p
4h 34m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
Depart: Sun May 29 2016 Return: Sun Jun 5 2016 Trip spans 8 days
Southwest
Southwest
MDW
6:10a
MCO
11:40a
5h 30m
nonstop
MCO
6:30p
MDW
9:10p
2h 40m
nonstop
Depart: Tue May 10 2016 Return: Sat May 14 2016 Trip spans 5 days
Delta
Delta
MDW
8:20a
MCO
12:26p
4h 06m
1 stop
MCO
7:30a
MDW
11:57a
4h 27m
1 stop
Depart: Tue Aug 30 2016 Return: Tue Sep 6 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
3:05a
MCO
7:29a
4h 24m
1 stop
MCO
4:15a
MDW
11:39a
7h 24m
1 stop
Depart: Wed May 11 2016 Return: Sat May 14 2016 Trip spans 4 days
Delta
Delta
MDW
8:20a
MCO
12:26p
4h 06m
1 stop
MCO
7:30a
MDW
11:57a
4h 27m
1 stop
Depart: Sun May 22 2016 Return: Tue May 24 2016 Trip spans 3 days
Southwest
Southwest
MDW
2:10a
MCO
4:50a
2h 40m
nonstop
MCO
3:05a
MDW
5:50a
2h 45m
nonstop
Depart: Thu May 12 2016 Return: Sat May 14 2016 Trip spans 3 days
Delta
Delta
MDW
2:30a
MCO
8:24a
5h 54m
1 stop
MCO
5:30a
MDW
11:57a
6h 27m
1 stop
Depart: Fri May 13 2016 Return: Mon May 16 2016 Trip spans 4 days
Delta
Delta
MDW
5:07a
MCO
12:44p
7h 37m
1 stop
MCO
10:19a
MDW
6:27p
8h 08m
1 stop
Depart: Wed Oct 26 2016 Return: Sun Oct 30 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
5:10a
MCO
11:31a
6h 21m
1 stop
MCO
2:20a
MDW
6:36a
4h 16m
1 stop
Depart: Mon May 16 2016 Return: Wed May 18 2016 Trip spans 3 days
Delta
Delta
MDW
3:15p
MCO
7:38p
4h 23m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
Depart: Sun May 15 2016 Return: Fri May 20 2016 Trip spans 6 days
Southwest
Southwest
MDW
2:10a
MCO
4:50a
2h 40m
nonstop
MCO
6:00p
MDW
8:40p
2h 40m
nonstop
Depart: Tue May 17 2016 Return: Wed May 18 2016 Trip spans 2 days
Delta
Delta
MDW
3:15p
MCO
7:38p
4h 23m
1 stop
MCO
5:30a
MDW
10:18a
4h 48m
1 stop
Depart: Sat Oct 15 2016 Return: Sat Oct 22 2016 Trip spans 8 days
Southwest
Southwest
MDW
11:05a
MCO
4:25p
5h 20m
nonstop
MCO
6:10a
MDW
9:00a
2h 50m
nonstop
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
878 5:35 am 9:10 am Jun 5 - Jul 1
2219 6:10 am 9:50 am May 31 - Jun 3
2219 6:10 am 9:50 am Apr 28 - May 29
2200 6:35 am 10:15 am Jun 5 - Jul 1
2206 6:40 am 10:15 am Apr 30 - May 21
2206 6:40 am 10:20 am Jun 4 - Jun 4
4191 6:40 am 10:20 am May 28 - May 28
153 7:30 am 11:05 am Jun 4 - Jun 4
2201 7:30 am 11:05 am Apr 30 - May 28
1553 7:35 am 11:05 am Jun 6 - Jul 1
1649 7:35 am 11:10 am Apr 28 - May 27
1649 7:35 am 11:10 am May 31 - Jun 3
1649 7:35 am 11:10 am May 1 - May 22
1891 7:35 am 11:10 am May 30 - May 30
4547 7:35 am 11:05 am Jun 5 - Jun 26
6313 7:35 am 11:10 am May 29 - May 29
119 8:30 am 12:00 pm Jun 4 - Jun 4
3190 8:30 am 12:00 pm May 28 - May 28
755 8:30 am 12:00 pm Apr 30 - May 21
3509 9:00 am 12:35 pm Apr 30 - Jun 4
1189 9:45 am 1:25 pm Jun 5 - Jun 26
2172 9:50 am 1:20 pm Jun 6 - Jul 1
3846 10:00 am 1:30 pm May 31 - Jun 3
3846 10:00 am 1:30 pm Apr 28 - May 27
6309 10:00 am 1:30 pm May 30 - May 30
922 10:20 am 1:50 pm May 29 - May 29
2171 10:50 am 2:25 pm Apr 30 - Jun 4
2782 1:15 pm 4:55 pm Jun 5 - Jul 1
2638 1:35 pm 5:15 pm Apr 30 - May 28
2638 1:40 pm 5:20 pm Jun 4 - Jun 4
3885 1:40 pm 5:15 pm May 31 - Jun 3
3885 1:40 pm 5:15 pm May 1 - May 22
3885 1:40 pm 5:15 pm Apr 28 - May 27
541 1:40 pm 5:15 pm May 30 - May 30
541 1:40 pm 5:15 pm May 29 - May 29
126 2:10 pm 5:50 pm Jun 5 - Jun 26
987 2:10 pm 5:50 pm Jun 6 - Jul 1
2063 2:50 pm 6:20 pm May 30 - May 30
3315 2:50 pm 6:20 pm May 29 - May 29
3315 2:50 pm 6:20 pm Apr 28 - May 27
3315 2:50 pm 6:20 pm May 31 - Jun 3
1154 3:10 pm 6:50 pm Jun 6 - Jun 10
238 3:10 pm 6:50 pm Jun 5 - Jun 5
1330 4:50 pm 8:25 pm Apr 30 - Jun 4
1685 5:50 pm 9:25 pm May 6 - May 27
1685 5:50 pm 9:25 pm Apr 30 - May 21
1685 5:50 pm 9:25 pm May 31 - Jun 3
1685 5:50 pm 9:25 pm Jun 4 - Jun 4
2851 5:50 pm 9:25 pm May 29 - May 29
5071 5:50 pm 9:25 pm May 30 - May 30
5071 5:50 pm 9:25 pm May 28 - May 28
33 6:45 pm 10:20 pm Apr 30 - Jun 4
313 7:30 pm 11:05 pm May 31 - Jun 3
313 7:30 pm 11:05 pm Apr 28 - May 27
4259 7:35 pm 11:10 pm May 29 - May 30
1953 7:40 pm 11:10 pm Jun 5 - Jul 1
5657 8:40 pm 12:15 am Jun 5 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We aggregate tons 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 don'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.

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
$191
Destination

Orlando
$191