Find Deals on Flights from Dallas to Chicago Midway

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 Dallas to Chicago Midway

(Round-trip)
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
Southwest
Southwest
DAL
2:35p
MDW
4:40p
2h 05m
nonstop
MDW
1:40a
DAL
4:00a
2h 20m
nonstop
Depart: Tue Apr 11 2017 Return: Sat Apr 15 2017 Trip spans 5 days
Delta
Delta
DFW
4:05a
MDW
9:33a
5h 28m
1 stop
MDW
2:25a
DFW
7:58a
5h 33m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Southwest
Southwest
DAL
4:20p
MDW
6:25p
2h 05m
nonstop
MDW
7:35a
DAL
9:55a
2h 20m
nonstop
Depart: Tue Apr 18 2017 Return: Fri Apr 21 2017 Trip spans 4 days
Delta
Delta
DAL
8:52a
MDW
4:20p
7h 28m
1 stop
MDW
2:00a
DAL
8:12a
6h 12m
1 stop
Depart: Sat May 13 2017 Return: Tue May 16 2017 Trip spans 4 days
Southwest
Southwest
DAL
4:20p
MDW
6:25p
2h 05m
nonstop
MDW
9:25a
DAL
11:45a
2h 20m
nonstop
Depart: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
DFW
12:01p
MDW
6:25p
6h 24m
1 stop
MDW
3:20a
DFW
8:55a
5h 35m
1 stop
Depart: Thu Jun 8 2017 Return: Sun Jun 11 2017 Trip spans 4 days
Major Airline
Major Airline
DAL
1:00a
MDW
2:35a
1h 35m
nonstop
MDW
1:00a
DAL
2:35a
1h 35m
nonstop
Depart: Wed Apr 26 2017 Return: Thu May 4 2017 Trip spans 9 days
Delta
Delta
DAL
3:00a
MDW
7:48a
4h 48m
1 stop
MDW
2:00a
DAL
8:00a
6h 00m
1 stop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Southwest
Southwest
DAL
3:45p
MDW
5:50p
2h 05m
nonstop
MDW
4:35p
DAL
6:55p
2h 20m
nonstop
Depart: Mon May 1 2017 Return: Thu May 4 2017 Trip spans 4 days
Delta
Delta
DFW
9:30a
MDW
4:00p
6h 30m
1 stop
MDW
6:21a
DFW
11:24a
5h 03m
1 stop
Depart: Sun May 7 2017 Return: Tue May 9 2017 Trip spans 3 days
Southwest
Southwest
DAL
2:05a
MDW
4:15a
2h 10m
nonstop
MDW
1:40a
DAL
4:00a
2h 20m
nonstop
Depart: Tue May 2 2017 Return: Thu May 11 2017 Trip spans 10 days
Delta
Delta
DFW
8:15a
MDW
1:17p
5h 02m
1 stop
MDW
5:10a
DFW
11:54a
6h 44m
1 stop
Depart: Sun May 14 2017 Return: Tue May 16 2017 Trip spans 3 days
Southwest
Southwest
DAL
3:25a
MDW
5:35a
2h 10m
nonstop
MDW
1:40a
DAL
4:00a
2h 20m
nonstop
Depart: Wed May 3 2017 Return: Sat May 6 2017 Trip spans 4 days
Delta
Delta
DFW
10:59a
MDW
4:00p
5h 01m
1 stop
MDW
11:55a
DFW
5:27p
5h 32m
1 stop
Depart: Thu May 4 2017 Return: Sat May 6 2017 Trip spans 3 days
Delta
Delta
DFW
2:35a
MDW
7:38a
5h 03m
1 stop
MDW
11:20a
DFW
6:43p
7h 23m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
Southwest
Southwest
DAL
2:05a
MDW
4:15a
2h 10m
nonstop
MDW
4:35p
DAL
6:55p
2h 20m
nonstop
Depart: Mon May 8 2017 Return: Sat May 20 2017 Trip spans 13 days
Delta
Delta
DFW
8:15a
MDW
1:17p
5h 02m
1 stop
MDW
2:30a
DFW
9:50a
7h 20m
1 stop
Depart: Sun Apr 30 2017 Return: Tue May 2 2017 Trip spans 3 days
Southwest
Southwest
DAL
3:25a
MDW
5:35a
2h 10m
nonstop
MDW
9:25a
DAL
11:45a
2h 20m
nonstop
Depart: Tue May 9 2017 Return: Wed May 10 2017 Trip spans 2 days
Delta
Delta
DFW
10:59a
MDW
4:00p
5h 01m
1 stop
MDW
3:20a
DFW
10:19a
6h 59m
1 stop
Depart: Fri May 12 2017 Return: Tue May 16 2017 Trip spans 5 days
Southwest
Southwest
DAL
2:05a
MDW
4:15a
2h 10m
nonstop
MDW
9:25a
DAL
11:45a
2h 20m
nonstop
* 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

Dallas
only $226
only $217
Destination

Chicago
$217
Airlines Airline reviews

5 travelers who booked a flight from Dallas to Chicago rated their chosen airlines with an average of 6.7.

Overall
6.4
Boarding
6.8
Crew
7.2
Comfort
7.2
Food
6.4
Entertainment
4.8