Find Cheap Flights from Dallas Love Field to Chicago (DAL - CHI)

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 Love Field to Chicago

(Round-trip)
Depart: Fri Dec 8 2017 Return: Sat Dec 9 2017 Trip spans 2 days
Southwest
Southwest
DAL
MDW
2h 10m
nonstop
MDW
DAL
2h 25m
nonstop
Depart: Mon Dec 11 2017 Return: Wed Dec 13 2017 Trip spans 3 days
Delta
Delta
DAL
MDW
5h 29m
1 stop
MDW
DAL
4h 51m
1 stop
Depart: Mon Dec 11 2017 Return: Sun Dec 17 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
DAL
MDW
5h 29m
1 stop
MDW
DAL
6h 34m
1 stop
Depart: Tue Dec 12 2017 Return: Wed Dec 13 2017 Trip spans 2 days
Virgin America
Virgin America
DAL
ORD
10h 52m
1 stop
ORD
DAL
8h 26m
1 stop
Depart: Wed Jan 24 2018 Return: Wed Feb 14 2018 Trip spans 22 days
Delta
Delta
DAL
MDW
7h 22m
1 stop
MDW
DAL
5h 52m
1 stop
Depart: Sun Nov 19 2017 Return: Tue Dec 5 2017 Trip spans 17 days
Multiple Airlines
Multiple Airlines
DAL
ORD
5h 42m
1 stop
ORD
DAL
8h 26m
1 stop
Depart: Wed Feb 7 2018 Return: Wed Feb 14 2018 Trip spans 8 days
Delta
Delta
DAL
MDW
4h 52m
1 stop
MDW
DAL
6h 22m
1 stop
Depart: Tue Dec 5 2017 Return: Sat Dec 9 2017 Trip spans 5 days
Southwest
Southwest
DAL
MDW
2h 05m
nonstop
MDW
DAL
2h 25m
nonstop
Depart: Sat Mar 3 2018 Return: Tue Mar 6 2018 Trip spans 4 days
Delta
Delta
DAL
MDW
6h 09m
1 stop
MDW
DAL
5h 53m
1 stop
Depart: Wed Nov 29 2017 Return: Sat Dec 2 2017 Trip spans 4 days
Delta
Delta
DAL
MDW
4h 49m
1 stop
MDW
DAL
6h 04m
1 stop
Depart: Fri Dec 8 2017 Return: Sat Dec 9 2017 Trip spans 2 days
Multiple Airlines
Multiple Airlines
DAL
ORD
5h 25m
1 stop
ORD
DAL
6h 34m
1 stop
Depart: Fri Jan 19 2018 Return: Tue Jan 23 2018 Trip spans 5 days
Virgin America
Virgin America
DAL
ORD
9h 40m
1 stop
ORD
DAL
28h 06m
1 stop
Depart: Tue Jan 9 2018 Return: Fri Jan 12 2018 Trip spans 4 days
Delta
Delta
DAL
MDW
5h 31m
1 stop
MDW
DAL
5h 53m
1 stop
Depart: Wed Jan 24 2018 Return: Wed Jan 31 2018 Trip spans 8 days
Virgin America
Virgin America
DAL
ORD
9h 40m
1 stop
ORD
DAL
21h 53m
1 stop
Depart: Thu Dec 28 2017 Return: Tue Jan 2 2018 Trip spans 6 days
Southwest
Southwest
DAL
MDW
2h 05m
nonstop
MDW
DAL
4h 30m
1 stop
Depart: Fri Dec 15 2017 Return: Mon Dec 18 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
DAL
MDW
4h 49m
1 stop
MDW
DAL
6h 34m
1 stop
Depart: Thu Feb 8 2018 Return: Sat Feb 10 2018 Trip spans 3 days
Delta
Delta
DAL
MDW
4h 52m
1 stop
MDW
DAL
5h 22m
1 stop
Depart: Thu Jan 25 2018 Return: Mon Jan 29 2018 Trip spans 5 days
Virgin America
Virgin America
DAL
ORD
9h 40m
1 stop
ORD
DAL
18h 48m
1 stop
Depart: Fri Jan 12 2018 Return: Mon Jan 15 2018 Trip spans 4 days
Southwest
Southwest
DAL
MDW
2h 10m
nonstop
MDW
DAL
2h 20m
nonstop
Depart: Sat Mar 3 2018 Return: Tue Mar 6 2018 Trip spans 4 days
Delta
Delta
DAL
ORD
5h 10m
1 stop
ORD
DAL
6h 37m
1 stop
Select an airline:  Southwest
Direct flights DAL to CHI on Southwest
Flight # Depart DAL Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
181 6:00 am 8:10 am Dec 1 - Dec 19
181 6:00 am 8:10 am Nov 23 - Nov 30
1164 6:05 am 8:15 am Dec 20 - Dec 28
1164 6:05 am 8:15 am Dec 22 - Dec 26
1164 6:05 am 8:15 am Nov 22 - Nov 27
2256 6:05 am 8:15 am Nov 18 - Nov 25
2256 6:45 am 8:55 am Dec 23 - Dec 30
2471 7:00 am 9:10 am Dec 2 - Dec 16
6809 7:25 am 9:30 am Dec 10 - Dec 17
6809 7:25 am 9:30 am Nov 26 - Dec 3
6809 7:25 am 9:30 am Dec 20 - Jan 2
2281 7:35 am 9:40 am Dec 23 - Dec 30
2281 7:35 am 9:40 am Nov 18 - Nov 25
192 9:40 am 11:45 am Nov 24 - Nov 24
8 9:40 am 11:45 am Dec 25 - Dec 25
8 9:40 am 11:45 am Nov 28 - Dec 19
2515 10:40 am 12:45 pm Dec 2 - Dec 16
226 11:50 am 1:55 pm Dec 24 - Dec 24
3569 11:50 am 1:55 pm Dec 3 - Dec 17
506 12:15 pm 2:20 pm Dec 25 - Dec 25
6026 12:15 pm 2:20 pm Dec 4 - Dec 19
6026 12:15 pm 2:20 pm Nov 23 - Dec 1
1370 12:40 pm 2:45 pm Nov 25 - Nov 25
6425 12:40 pm 2:45 pm Dec 23 - Dec 30
1244 12:55 pm 3:00 pm Dec 20 - Dec 28
1916 12:55 pm 3:00 pm Dec 22 - Dec 26
1916 12:55 pm 3:00 pm Nov 22 - Nov 27
3200 2:05 pm 4:10 pm Dec 3 - Dec 17
3200 2:05 pm 4:10 pm Dec 24 - Dec 24
5693 2:15 pm 4:20 pm Dec 25 - Dec 25
5140 2:20 pm 4:25 pm Nov 26 - Nov 27
5140 2:20 pm 4:25 pm Dec 20 - Jan 2
5693 2:25 pm 4:30 pm Nov 24 - Dec 1
5693 2:25 pm 4:30 pm Dec 4 - Dec 19
2311 3:15 pm 5:25 pm Dec 2 - Dec 16
32 3:40 pm 5:45 pm Nov 22 - Nov 27
32 3:40 pm 5:45 pm Dec 22 - Dec 26
5188 3:40 pm 5:45 pm Dec 20 - Dec 28
1205 5:05 pm 7:10 pm Dec 25 - Dec 25
205 5:05 pm 7:10 pm Nov 24 - Nov 24
38 5:05 pm 7:10 pm Nov 28 - Dec 8
38 5:05 pm 7:10 pm Dec 12 - Dec 19
38 5:05 pm 7:10 pm Dec 11 - Dec 11
5394 5:40 pm 7:45 pm Dec 3 - Dec 17
5394 5:40 pm 7:45 pm Dec 24 - Dec 24
1826 5:45 pm 7:50 pm Dec 20 - Jan 2
1826 5:45 pm 7:50 pm Nov 26 - Nov 27
6200 5:45 pm 7:50 pm Nov 18 - Nov 25
6200 5:45 pm 7:50 pm Dec 23 - Dec 30
1287 6:25 pm 8:30 pm Nov 28 - Dec 19
1287 6:25 pm 8:30 pm Dec 25 - Dec 25
1882 6:25 pm 8:30 pm Nov 24 - Nov 24
2135 6:25 pm 8:30 pm Dec 2 - Dec 16
4906 8:00 pm 10:05 pm Dec 3 - Dec 17
4906 8:00 pm 10:05 pm Dec 24 - Dec 24
2123 8:05 pm 10:10 pm Nov 18 - Nov 25
2123 8:05 pm 10:10 pm Dec 23 - Dec 30
2783 8:15 pm 10:20 pm Dec 2 - Dec 16
2148 8:55 pm 11:00 pm Dec 23 - Dec 30
3560 9:00 pm 11:10 pm Dec 3 - Dec 17
5335 9:10 pm 11:15 pm Dec 20 - Jan 2
5335 9:10 pm 11:15 pm Nov 26 - Nov 27
434 9:35 pm 11:40 pm Nov 25 - Nov 25
1108 10:10 pm 12:20 am Nov 28 - Dec 19
3253 10:10 pm 12:20 am Nov 24 - Nov 24
* 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 and someone from our team will get back to you promptly.

Airports
Origin

Dallas
$128
Destination

Chicago
only $224
only $128