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.
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Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
4:15a
4h 15m
1 stop
MDW
12:00a
MCO
5:48a
5h 48m
1 stop
Depart: Fri Jan 26 2018 Return: Sun Jan 28 2018 Trip spans 3 days
Delta
Delta
MCO
12:00a
MDW
6:54a
6h 54m
1 stop
MDW
12:00a
MCO
4:52a
4h 52m
1 stop
Depart: Thu Feb 1 2018 Return: Mon Feb 5 2018 Trip spans 5 days
Delta
Delta
MCO
12:00a
MDW
5:20a
5h 20m
1 stop
MDW
12:00a
MCO
4:34a
4h 34m
1 stop
Depart: Wed Feb 28 2018 Return: Sun Mar 4 2018 Trip spans 5 days
Delta
Delta
MCO
12:00a
MDW
4:51a
4h 51m
1 stop
MDW
12:00a
MCO
5:49a
5h 49m
1 stop
Depart: Thu Mar 1 2018 Return: Sun Mar 4 2018 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
4:21a
4h 21m
1 stop
MDW
12:00a
MCO
5:49a
5h 49m
1 stop
Depart: Tue Dec 5 2017 Return: Sat Dec 9 2017 Trip spans 5 days
Delta
Delta
MCO
12:00a
MDW
6:05a
6h 05m
1 stop
MDW
12:00a
MCO
6:23a
6h 23m
1 stop
Depart: Fri Mar 2 2018 Return: Mon Mar 5 2018 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
5:15a
5h 15m
1 stop
MDW
12:00a
MCO
4:43a
4h 43m
1 stop
Depart: Thu Apr 26 2018 Return: Sun Apr 29 2018 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
5:39a
5h 39m
1 stop
MDW
12:00a
MCO
5:49a
5h 49m
1 stop
Depart: Fri May 11 2018 Return: Sat May 12 2018 Trip spans 2 days
Delta
Delta
MCO
12:00a
MDW
5:15a
5h 15m
1 stop
MDW
12:00a
MCO
4:40a
4h 40m
1 stop
Depart: Thu Dec 14 2017 Return: Sun Dec 17 2017 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
4:35a
4h 35m
1 stop
MDW
12:00a
MCO
5:24a
5h 24m
1 stop
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
6:05a
6h 05m
1 stop
MDW
12:00a
MCO
5:05a
5h 05m
1 stop
Depart: Wed Nov 22 2017 Return: Tue Dec 12 2017 Trip spans 21 days
Delta
Delta
MCO
12:00a
MDW
5:35a
5h 35m
1 stop
MDW
12:00a
MCO
5:16a
5h 16m
1 stop
Depart: Thu Nov 30 2017 Return: Sun Dec 3 2017 Trip spans 4 days
Delta
Delta
MCO
12:00a
MDW
4:35a
4h 35m
1 stop
MDW
12:00a
MCO
5:33a
5h 33m
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
1211 6:05 am 7:55 am Nov 28 - Dec 19
1527 6:05 am 7:55 am Dec 25 - Dec 25
1211 6:20 am 8:10 am Nov 23 - Nov 25
5742 6:50 am 8:40 am Nov 26 - Nov 27
5742 6:50 am 8:40 am Dec 20 - Jan 2
2677 6:55 am 8:45 am Dec 23 - Dec 30
5919 7:25 am 9:15 am Dec 11 - Dec 11
5683 8:25 am 10:15 am Dec 25 - Dec 25
2867 9:00 am 10:50 am Dec 2 - Dec 16
4617 9:30 am 11:20 am Dec 24 - Dec 24
1521 9:35 am 11:20 am Nov 24 - Nov 24
955 9:35 am 11:20 am Dec 11 - Dec 19
955 9:35 am 11:20 am Nov 28 - Dec 8
2501 9:40 am 11:25 am Nov 18 - Nov 25
2501 9:40 am 11:25 am Dec 23 - Dec 30
4617 10:15 am 12:00 pm Dec 3 - Dec 17
164 10:20 am 12:05 pm Dec 22 - Dec 26
164 10:20 am 12:05 pm Nov 22 - Nov 27
4462 10:20 am 12:05 pm Dec 2 - Dec 16
6914 10:20 am 12:05 pm Dec 20 - Dec 28
489 10:55 am 12:45 pm Nov 24 - Dec 1
489 10:55 am 12:45 pm Dec 4 - Dec 19
489 10:55 am 12:45 pm Dec 25 - Jan 1
3586 11:25 am 1:10 pm Dec 3 - Dec 17
3586 11:25 am 1:10 pm Dec 24 - Dec 24
2095 11:40 am 1:25 pm Dec 23 - Dec 30
2095 11:40 am 1:25 pm Nov 18 - Nov 25
6022 11:45 am 1:35 pm Dec 25 - Dec 25
4393 12:20 pm 2:10 pm Dec 2 - Dec 16
4706 12:35 pm 2:20 pm Dec 24 - Dec 24
5591 12:35 pm 2:20 pm Dec 3 - Dec 17
6478 12:40 pm 2:25 pm Nov 26 - Nov 27
6478 12:40 pm 2:25 pm Dec 20 - Jan 2
2065 1:00 pm 2:45 pm Dec 23 - Dec 30
236 1:00 pm 2:45 pm Nov 25 - Nov 25
2852 1:20 pm 3:05 pm Dec 2 - Dec 16
5427 1:25 pm 3:10 pm Dec 25 - Dec 25
5427 1:25 pm 3:10 pm Dec 4 - Dec 19
5427 1:25 pm 3:10 pm Nov 23 - Dec 1
1021 3:00 pm 4:50 pm Nov 22 - Nov 27
1021 3:00 pm 4:50 pm Dec 22 - Dec 26
5061 3:00 pm 4:50 pm Dec 20 - Dec 28
5181 3:15 pm 5:05 pm Dec 9 - Dec 9
397 3:45 pm 5:30 pm Nov 28 - Dec 8
397 3:45 pm 5:30 pm Dec 12 - Dec 19
397 3:45 pm 5:30 pm Dec 11 - Dec 11
397 3:45 pm 5:30 pm Dec 25 - Dec 25
397 3:45 pm 5:30 pm Nov 24 - Nov 24
1742 4:15 pm 6:00 pm Dec 22 - Dec 26
1742 4:15 pm 6:00 pm Nov 22 - Nov 27
2804 4:15 pm 6:00 pm Dec 20 - Dec 28
5737 4:50 pm 6:40 pm Nov 24 - Nov 24
2958 5:25 pm 7:15 pm Dec 2 - Dec 16
3862 5:30 pm 7:20 pm Nov 26 - Nov 27
3862 5:30 pm 7:20 pm Dec 20 - Jan 2
4071 5:30 pm 7:20 pm Dec 23 - Dec 30
4071 5:30 pm 7:20 pm Nov 18 - Nov 25
4859 5:55 pm 7:45 pm Dec 24 - Dec 24
4859 6:25 pm 8:15 pm Dec 3 - Dec 17
1284 6:40 pm 8:25 pm Nov 25 - Nov 25
2504 6:40 pm 8:25 pm Dec 23 - Dec 30
160 6:55 pm 8:45 pm Nov 28 - Dec 19
705 6:55 pm 8:45 pm Dec 25 - Dec 25
2181 7:05 pm 8:55 pm Nov 26 - Nov 27
2181 7:10 pm 9:00 pm Dec 20 - Jan 2
2327 7:10 pm 9:00 pm Dec 2 - Dec 16
4875 8:10 pm 9:55 pm Dec 23 - Dec 30
4875 8:10 pm 9:55 pm Nov 18 - Nov 25
3571 8:15 pm 10:00 pm Dec 3 - Dec 17
1614 8:25 pm 10:10 pm Nov 28 - Dec 19
3341 8:30 pm 10:15 pm Nov 24 - Nov 24
4166 8:30 pm 10:15 pm Dec 2 - Dec 16
1797 8:40 pm 10:25 pm Dec 24 - Dec 24
1614 8:50 pm 10:35 pm Dec 25 - Dec 25
6221 9:15 pm 11:00 pm Dec 3 - Jan 7
4141 9:55 pm 11:45 pm Dec 23 - Dec 30
4141 9:55 pm 11:45 pm Nov 18 - Nov 25
5399 9:55 pm 11:45 pm Nov 24 - Dec 1
5399 9:55 pm 11:45 pm Dec 2 - Dec 19
5626 10:25 pm 12:10 am Dec 3 - Jan 7
6284 10:55 pm 12:40 am Dec 20 - Jan 2
6284 10:55 pm 12:40 am Nov 26 - Nov 27
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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.

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Airports
Origin

Orlando
$174
Destination

Chicago
$174
Airlines