Find Deals on Flights from Orlando to Chicago Midway (ORL - 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: Thu Aug 25 2016 Return: Mon Aug 29 2016 Trip spans 5 days
Depart: Wed Aug 24 2016 Return: Fri Aug 26 2016 Trip spans 3 days
Depart: Wed Aug 17 2016 Return: Sat Aug 20 2016 Trip spans 4 days
Depart: Thu Sep 22 2016 Return: Mon Sep 26 2016 Trip spans 5 days
Depart: Mon Aug 1 2016 Return: Wed Aug 10 2016 Trip spans 10 days
Depart: Fri Aug 26 2016 Return: Sun Aug 28 2016 Trip spans 3 days
Depart: Wed Aug 10 2016 Return: Mon Aug 15 2016 Trip spans 6 days
Depart: Sat Aug 27 2016 Return: Tue Aug 30 2016 Trip spans 4 days
Depart: Fri Sep 9 2016 Return: Mon Sep 12 2016 Trip spans 4 days
Depart: Mon Aug 29 2016 Return: Thu Sep 1 2016 Trip spans 4 days
Depart: Fri Aug 19 2016 Return: Mon Aug 22 2016 Trip spans 4 days
Depart: Tue Aug 30 2016 Return: Fri Sep 2 2016 Trip spans 4 days
Depart: Wed Aug 31 2016 Return: Sat Sep 3 2016 Trip spans 4 days
Depart: Fri Sep 2 2016 Return: Wed Sep 7 2016 Trip spans 6 days
Depart: Thu Jul 28 2016 Return: Mon Aug 1 2016 Trip spans 5 days
Depart: Sat Sep 3 2016 Return: Tue Sep 6 2016 Trip spans 4 days
Depart: Sun Sep 4 2016 Return: Sun Sep 11 2016 Trip spans 8 days
Depart: Wed Sep 7 2016 Return: Fri Sep 9 2016 Trip spans 3 days
Depart: Sat Aug 13 2016 Return: Wed Aug 17 2016 Trip spans 5 days
Depart: Thu Sep 8 2016 Return: Fri Sep 9 2016 Trip spans 2 days
Select an airline:  Southwest
Direct flights ORL to MDW on Southwest
Flight # Depart MCO Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
2788 7:25 am 9:05 am Aug 8 - Sep 2
3468 7:25 am 9:05 am Jul 21 - Aug 5
5774 7:30 am 9:10 am Jul 23 - Aug 6
136 8:20 am 10:00 am Jul 21 - Aug 5
1014 8:25 am 10:05 am Aug 13 - Aug 27
510 8:35 am 10:15 am Aug 8 - Sep 2
525 9:10 am 10:50 am Jul 23 - Jul 30
525 9:10 am 10:50 am Aug 6 - Aug 6
6556 9:25 am 11:05 am Jul 24 - Jul 31
2559 10:10 am 11:55 am Aug 13 - Aug 27
3599 10:25 am 12:05 pm Jul 21 - Aug 5
639 11:05 am 12:45 pm Jul 23 - Jul 30
639 11:05 am 12:45 pm Aug 6 - Aug 6
3813 11:45 am 1:30 pm Aug 13 - Aug 27
407 11:55 am 1:40 pm Aug 7 - Sep 2
1356 12:05 pm 1:50 pm Jul 21 - Aug 5
6218 12:15 pm 2:00 pm Aug 6 - Aug 6
6218 12:15 pm 2:00 pm Jul 23 - Jul 30
3251 12:45 pm 2:25 pm Aug 13 - Aug 27
1210 1:20 pm 3:05 pm Aug 7 - Nov 4
2981 1:30 pm 3:15 pm Aug 13 - Aug 27
5450 1:30 pm 3:15 pm Jul 23 - Aug 6
2005 2:10 pm 3:55 pm Jul 21 - Aug 5
3996 3:10 pm 5:00 pm Aug 6 - Aug 6
3996 3:10 pm 5:00 pm Jul 23 - Jul 30
1580 3:25 pm 5:10 pm Aug 7 - Sep 2
1076 3:30 pm 5:15 pm Aug 13 - Aug 27
2157 4:00 pm 5:50 pm Jul 23 - Aug 6
1422 4:10 pm 6:00 pm Jul 21 - Aug 5
3645 4:10 pm 5:55 pm Aug 13 - Aug 27
544 4:40 pm 6:30 pm Jul 30 - Jul 30
544 4:40 pm 6:30 pm Aug 6 - Aug 6
417 4:45 pm 6:30 pm Aug 7 - Sep 5
5860 5:25 pm 7:10 pm Jul 23 - Aug 6
1167 5:40 pm 7:25 pm Jul 21 - Aug 5
1716 6:00 pm 7:40 pm Aug 7 - Sep 2
856 6:05 pm 7:50 pm Aug 13 - Aug 27
204 7:10 pm 8:55 pm Aug 8 - Sep 30
5581 7:10 pm 8:55 pm Aug 7 - Aug 28
6233 7:15 pm 9:05 pm Jul 23 - Aug 6
861 7:55 pm 9:40 pm Aug 13 - Aug 27
1480 8:40 pm 10:30 pm Jul 21 - Aug 5
967 9:10 pm 10:55 pm Aug 13 - Aug 27
5076 10:25 pm 12:05 am Jul 23 - Aug 6
556 10:30 pm 12:10 am Jul 21 - Aug 5
* 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
$124
Destination

Chicago
$124
Airlines