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

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 Orlando to Chicago Midway

(Round-trip)
Depart: Tue May 9 2017 Return: Mon May 15 2017 Trip spans 7 days
Delta
Delta
MCO
3:20a
MDW
8:29a
5h 09m
1 stop
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
Depart: Wed May 10 2017 Return: Thu May 11 2017 Trip spans 2 days
Delta
Delta
MCO
3:50a
MDW
8:29a
4h 39m
1 stop
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
Depart: Thu May 11 2017 Return: Sun May 14 2017 Trip spans 4 days
Delta
Delta
MCO
2:20a
MDW
8:29a
6h 09m
1 stop
MDW
2:55a
MCO
7:46a
4h 51m
1 stop
Depart: Sun May 14 2017 Return: Wed May 17 2017 Trip spans 4 days
Delta
Delta
MCO
2:20a
MDW
6:46a
4h 26m
1 stop
MDW
6:21a
MCO
10:30a
4h 09m
1 stop
Depart: Tue May 16 2017 Return: Wed May 17 2017 Trip spans 2 days
Delta
Delta
MCO
1:25p
MDW
7:20p
5h 55m
1 stop
MDW
6:21a
MCO
11:28a
5h 07m
1 stop
Depart: Wed May 17 2017 Return: Fri May 19 2017 Trip spans 3 days
Delta
Delta
MCO
1:20a
MDW
6:46a
5h 26m
1 stop
MDW
1:00p
MCO
6:04p
5h 04m
1 stop
Depart: Wed May 24 2017 Return: Tue May 30 2017 Trip spans 7 days
Delta
Delta
MCO
10:14a
MDW
2:59p
4h 45m
1 stop
MDW
2:55a
MCO
7:46a
4h 51m
1 stop
Depart: Wed May 31 2017 Return: Mon Jun 5 2017 Trip spans 6 days
Delta
Delta
MCO
4:20a
MDW
8:29a
4h 09m
1 stop
MDW
3:20p
MCO
8:00p
4h 40m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Delta
Delta
MCO
4:25a
MDW
9:23a
4h 58m
1 stop
MDW
5:16a
MCO
10:03a
4h 47m
1 stop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Delta
Delta
MCO
6:15a
MDW
1:17p
7h 02m
1 stop
MDW
5:16a
MCO
10:03a
4h 47m
1 stop
Depart: Sun Jun 4 2017 Return: Wed Jun 7 2017 Trip spans 4 days
Delta
Delta
MCO
3:50a
MDW
8:29a
4h 39m
1 stop
MDW
5:16a
MCO
12:49p
7h 33m
1 stop
Depart: Mon Jun 5 2017 Return: Wed Jun 7 2017 Trip spans 3 days
Delta
Delta
MCO
2:15a
MDW
9:23a
7h 08m
1 stop
MDW
8:05a
MCO
12:26p
4h 21m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Delta
Delta
MCO
2:15a
MDW
9:23a
7h 08m
1 stop
MDW
9:00a
MCO
3:39p
6h 39m
1 stop
Depart: Wed Jun 7 2017 Return: Thu Jun 8 2017 Trip spans 2 days
Delta
Delta
MCO
8:15a
MDW
2:59p
6h 44m
1 stop
MDW
5:16a
MCO
12:49p
7h 33m
1 stop
Depart: Sat Jun 10 2017 Return: Mon Jun 19 2017 Trip spans 10 days
Delta
Delta
MCO
10:14a
MDW
5:34p
7h 20m
1 stop
MDW
3:53p
MCO
7:59p
4h 06m
1 stop
Depart: Tue Jun 13 2017 Return: Tue Jun 20 2017 Trip spans 8 days
Delta
Delta
MCO
11:17a
MDW
4:17p
5h 00m
1 stop
MDW
3:53p
MCO
7:59p
4h 06m
1 stop
Depart: Wed Jun 14 2017 Return: Tue Jun 20 2017 Trip spans 7 days
Delta
Delta
MCO
2:20a
MDW
6:35a
4h 15m
1 stop
MDW
3:53p
MCO
7:59p
4h 06m
1 stop
Depart: Wed Jun 21 2017 Return: Tue Jun 27 2017 Trip spans 7 days
Delta
Delta
MCO
2:25a
MDW
9:19a
6h 54m
1 stop
MDW
8:55a
MCO
5:39p
8h 44m
1 stop
Depart: Tue Jul 4 2017 Return: Thu Jul 6 2017 Trip spans 3 days
Delta
Delta
MCO
3:20a
MDW
10:10a
6h 50m
1 stop
MDW
9:40a
MCO
2:50p
5h 10m
1 stop
Depart: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
Delta
Delta
MCO
5:20a
MDW
10:07a
4h 47m
1 stop
MDW
3:20p
MCO
7:57p
4h 37m
1 stop
Select an airline:  Southwest
Direct flights MCO to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
5031 6:40 am 8:25 am Apr 29 - Jun 3
4336 7:15 am 9:00 am Apr 30 - May 28
1916 7:20 am 9:05 am Apr 25 - May 26
1916 7:20 am 9:05 am May 30 - Jun 2
1645 7:35 am 9:20 am May 29 - May 29
5617 9:15 am 11:00 am Apr 29 - Jun 3
1973 9:25 am 11:10 am May 30 - Jun 2
1973 9:25 am 11:10 am Apr 25 - May 26
1305 10:05 am 11:50 am May 29 - May 29
4520 10:30 am 12:15 pm Apr 30 - May 28
4406 11:20 am 1:05 pm Apr 29 - Jun 3
4395 12:20 pm 2:05 pm Apr 29 - Jun 3
1525 12:40 pm 2:25 pm May 28 - May 28
4833 12:40 pm 2:25 pm Apr 30 - May 7
4833 12:40 pm 2:25 pm May 14 - May 21
3948 12:45 pm 2:30 pm Apr 25 - Jun 2
196 2:20 pm 4:10 pm Apr 29 - Jun 3
741 3:15 pm 5:00 pm Apr 30 - May 28
3846 4:00 pm 5:45 pm Apr 25 - Jun 2
1801 5:15 pm 7:05 pm Apr 26 - Jun 2
2524 5:50 pm 7:40 pm May 13 - Jun 3
2524 5:50 pm 7:40 pm May 28 - May 28
2524 5:50 pm 7:40 pm Apr 29 - May 6
2981 5:50 pm 7:40 pm Apr 30 - May 21
4400 7:30 pm 9:20 pm Apr 29 - May 27
4023 7:55 pm 9:40 pm Apr 25 - Jun 2
571 8:10 pm 9:55 pm Apr 29 - Jun 3
3308 8:25 pm 10:10 pm Apr 30 - May 21
3308 8:25 pm 10:10 pm May 28 - May 28
2742 9:00 pm 10:45 pm May 13 - Jun 3
2742 9:00 pm 10:45 pm Apr 29 - May 6
2957 9:45 pm 11:25 pm Apr 30 - May 28
1324 10:25 pm 12:05 am Apr 25 - Jun 2
* 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

Orlando
$204
Destination

Chicago
$204
Airlines