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.
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Book cheap flights from Orlando to Chicago Midway

(Round-trip)
Depart: Sat Aug 27 2016 Return: Mon Aug 29 2016 Trip spans 3 days
Depart: Sat Oct 1 2016 Return: Mon Oct 3 2016 Trip spans 3 days
Depart: Tue Dec 13 2016 Return: Sat Dec 17 2016 Trip spans 5 days
Depart: Thu Oct 27 2016 Return: Mon Oct 31 2016 Trip spans 5 days
Depart: Thu Sep 8 2016 Return: Sat Sep 10 2016 Trip spans 3 days
Depart: Fri Sep 9 2016 Return: Mon Sep 12 2016 Trip spans 4 days
Depart: Fri Nov 4 2016 Return: Sat Nov 5 2016 Trip spans 2 days
Depart: Sat Sep 10 2016 Return: Mon Sep 12 2016 Trip spans 3 days
Depart: Fri Nov 11 2016 Return: Mon Nov 14 2016 Trip spans 4 days
Depart: Sun Sep 11 2016 Return: Mon Sep 12 2016 Trip spans 2 days
Depart: Thu Dec 1 2016 Return: Sat Dec 3 2016 Trip spans 3 days
Depart: Mon Sep 12 2016 Return: Wed Sep 14 2016 Trip spans 3 days
Depart: Tue Sep 13 2016 Return: Wed Sep 14 2016 Trip spans 2 days
Depart: Thu Feb 2 2017 Return: Mon Feb 6 2017 Trip spans 5 days
Depart: Wed Sep 14 2016 Return: Mon Sep 19 2016 Trip spans 6 days
Depart: Thu Sep 15 2016 Return: Mon Sep 19 2016 Trip spans 5 days
Depart: Fri Sep 16 2016 Return: Mon Sep 19 2016 Trip spans 4 days
Depart: Sat Sep 17 2016 Return: Mon Sep 19 2016 Trip spans 3 days
Depart: Mon Nov 14 2016 Return: Fri Nov 25 2016 Trip spans 12 days
Depart: Sun Sep 18 2016 Return: Thu Sep 22 2016 Trip spans 5 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 25 - Sep 2
2788 7:25 am 9:10 am Oct 3 - Nov 4
2788 7:25 am 9:05 am Sep 6 - Sep 30
1014 8:25 am 10:05 am Sep 10 - Oct 1
1267 8:25 am 10:05 am Sep 3 - Sep 3
117 8:35 am 10:15 am Sep 5 - Sep 5
510 8:35 am 10:15 am Aug 25 - Sep 2
820 8:35 am 10:20 am Oct 3 - Oct 28
5645 9:30 am 11:15 am Sep 5 - Sep 5
2559 10:00 am 11:45 am Sep 3 - Sep 3
2559 10:10 am 11:55 am Sep 10 - Oct 1
3813 11:45 am 1:30 pm Sep 10 - Oct 1
3813 11:45 am 1:30 pm Sep 3 - Sep 3
1301 11:55 am 1:40 pm Sep 4 - Sep 5
407 11:55 am 1:40 pm Sep 6 - Sep 30
407 11:55 am 1:40 pm Aug 25 - Sep 2
541 11:55 am 1:40 pm Oct 2 - Oct 30
681 11:55 am 1:40 pm Oct 3 - Oct 28
2248 12:45 pm 2:25 pm Sep 3 - Sep 3
3251 12:45 pm 2:25 pm Sep 10 - Sep 24
6545 12:45 pm 2:25 pm Oct 1 - Oct 1
1210 1:20 pm 3:05 pm Aug 25 - Nov 4
2981 1:30 pm 3:15 pm Sep 10 - Oct 1
1580 3:25 pm 5:10 pm Sep 4 - Sep 4
1580 3:25 pm 5:10 pm Sep 5 - Sep 30
1580 3:25 pm 5:15 pm Oct 2 - Nov 4
1580 3:25 pm 5:10 pm Aug 25 - Sep 2
1076 3:30 pm 5:15 pm Sep 10 - Oct 1
1303 3:30 pm 5:15 pm Sep 3 - Sep 3
3645 4:10 pm 5:55 pm Sep 10 - Oct 1
417 4:40 pm 6:30 pm Oct 2 - Oct 30
417 4:45 pm 6:30 pm Aug 25 - Sep 5
417 4:45 pm 6:30 pm Sep 6 - Sep 30
4536 5:00 pm 6:45 pm Sep 3 - Sep 3
1716 6:00 pm 7:40 pm Aug 25 - Sep 2
856 6:05 pm 7:50 pm Sep 10 - Oct 1
2196 7:00 pm 8:45 pm Sep 3 - Sep 3
204 7:05 pm 9:00 pm Oct 3 - Oct 28
173 7:10 pm 9:05 pm Oct 2 - Oct 30
204 7:10 pm 8:55 pm Aug 25 - Sep 30
5292 7:10 pm 8:55 pm Sep 4 - Sep 4
5581 7:10 pm 8:55 pm Sep 11 - Sep 25
861 7:55 pm 9:40 pm Sep 10 - Oct 1
* 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
$134
Destination

Chicago
$134
Airlines