Find Deals on Flights from San Diego to Chicago (SAN - 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 San Diego to Chicago

(Round-trip)
Depart: Mon May 16 2016 Return: Tue May 17 2016 Trip spans 2 days
Major Airline
Major Airline
SAN
ORD
4h 04m
nonstop
ORD
SAN
4h 21m
nonstop
Depart: Wed May 4 2016 Return: Fri May 6 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 07m
nonstop
ORD
SAN
4h 18m
nonstop
Depart: Wed Jun 8 2016 Return: Tue Jun 14 2016 Trip spans 7 days
United
United
SAN
ORD
4h 10m
nonstop
ORD
SAN
4h 22m
nonstop
Depart: Tue Aug 30 2016 Return: Sat Sep 3 2016 Trip spans 5 days
Frontier
Frontier
SAN
ORD
13h 11m
1 stop
ORD
SAN
18h 08m
1 stop
Depart: Wed Jun 1 2016 Return: Thu Jun 2 2016 Trip spans 2 days
Delta
Delta
SAN
MDW
8h 33m
1 stop
MDW
SAN
8h 53m
1 stop
Depart: Tue May 17 2016 Return: Sat May 21 2016 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 07m
nonstop
ORD
SAN
4h 18m
nonstop
Depart: Thu Sep 1 2016 Return: Sat Sep 10 2016 Trip spans 10 days
Southwest
Southwest
SAN
MDW
3h 50m
nonstop
MDW
SAN
5h 35m
nonstop
Depart: Wed May 18 2016 Return: Tue May 24 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 07m
nonstop
ORD
SAN
4h 18m
nonstop
Depart: Wed Aug 17 2016 Return: Tue Aug 23 2016 Trip spans 7 days
Major Airline
Major Airline
SAN
ORD
11h 48m
1 stop
ORD
SAN
7h 33m
1 stop
Depart: Sat Sep 24 2016 Return: Sat Oct 1 2016 Trip spans 8 days
Frontier
Frontier
SAN
ORD
11h 00m
1 stop
ORD
SAN
17h 17m
1 stop
Depart: Sat Aug 20 2016 Return: Tue Aug 23 2016 Trip spans 4 days
Major Airline
Major Airline
SAN
ORD
5h 50m
1 stop
ORD
SAN
6h 24m
1 stop
Depart: Sat Oct 8 2016 Return: Wed Oct 12 2016 Trip spans 5 days
Frontier
Frontier
SAN
ORD
11h 00m
1 stop
ORD
SAN
17h 17m
1 stop
Depart: Sat May 28 2016 Return: Thu Jun 2 2016 Trip spans 6 days
Delta
Delta
SAN
MDW
6h 26m
1 stop
MDW
SAN
6h 14m
1 stop
Depart: Fri May 13 2016 Return: Sun May 15 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 07m
nonstop
ORD
SAN
4h 18m
nonstop
Depart: Tue Aug 23 2016 Return: Tue Aug 30 2016 Trip spans 8 days
Major Airline
Major Airline
SAN
ORD
6h 22m
1 stop
ORD
SAN
8h 04m
1 stop
Depart: Mon May 30 2016 Return: Thu Jun 2 2016 Trip spans 4 days
Delta
Delta
SAN
MDW
6h 27m
1 stop
MDW
SAN
6h 14m
1 stop
Depart: Fri Aug 26 2016 Return: Wed Aug 31 2016 Trip spans 6 days
Delta
Delta
SAN
MDW
10h 21m
1 stop
MDW
SAN
8h 36m
1 stop
Depart: Tue Jun 28 2016 Return: Tue Jul 19 2016 Trip spans 22 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 08m
nonstop
ORD
SAN
5h 47m
1 stop
Depart: Sat Sep 10 2016 Return: Tue Sep 20 2016 Trip spans 11 days
Delta
Delta
SAN
MDW
8h 33m
1 stop
MDW
SAN
7h 31m
1 stop
Depart: Wed Jun 22 2016 Return: Tue Jun 28 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SAN
ORD
4h 08m
nonstop
ORD
SAN
4h 11m
nonstop
Direct flights SAN to CHI on American Airlines
Flight # Depart SAN Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1566 8:00 am 2:04 pm May 6 - May 18
1566 8:00 am 2:04 pm May 19 - Jun 1
1566 8:00 am 2:04 pm May 5 - May 12
1566 8:00 am 2:03 pm Jun 2 - Jul 2
934 9:45 am 3:54 pm Jun 2 - Jun 8
934 9:45 am 3:54 pm Jun 7 - Jun 30
934 9:45 am 3:54 pm Jun 10 - Jun 29
156 10:30 am 4:34 pm May 26 - May 26
156 10:40 am 4:44 pm May 19 - May 23
156 10:40 am 4:44 pm May 12 - May 12
156 10:40 am 4:44 pm May 27 - May 30
156 10:40 am 4:44 pm May 6 - May 16
156 10:40 am 4:44 pm May 29 - May 29
156 10:40 am 4:44 pm May 10 - Jun 1
156 11:20 am 5:29 pm Jun 8 - Aug 17
156 11:20 am 5:29 pm Jun 9 - Aug 4
156 11:20 am 5:29 pm Jun 2 - Jun 6
156 11:20 am 5:29 pm Jun 7 - Aug 16
156 11:20 am 5:29 pm Jun 10 - Aug 5
1296 2:58 pm 9:05 pm Jun 5 - Jun 26
1296 2:58 pm 9:05 pm Jun 4 - Jul 2
1296 2:58 pm 9:05 pm Jun 3 - Jul 1
1296 2:58 pm 9:05 pm Jun 2 - Jun 2
1296 3:00 pm 9:04 pm May 5 - Jun 1
1296 3:00 pm 9:04 pm May 7 - May 28
122 10:55 pm 4:59 am May 5 - May 24
122 10:55 pm 4:59 am May 25 - Jun 1
122 11:00 pm 5:09 am Jun 2 - Jun 29
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons 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 don'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.

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

San Diego
$147
Destination

Chicago
only $147
only $268