Take off on cheap flights from San Diego to Chicago, your adventure starts now!

Find cheap airline tickets from San Diego to Chicago by date

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$130
outward: Mar 7, 2019
12:05a PHL » 2:40a MCO
Spirit Airlines direct (2h35m)
inbound: Mar 10, 2019
6:40p MCO » 6:34p PHL
Unknown Company 1 stop (23h54m)
$165
outward: Sep 24, 2018
10:00p SAN » 2:09a ORD
Spirit Airlines direct (4h09m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$166
outward: Sep 24, 2018
10:00p SAN » 2:09a ORD
Spirit Airlines direct (4h09m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Sep 27, 2018
10:00p SAN » 2:09a ORD
Spirit Airlines direct (4h09m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$167
outward: Sep 27, 2018
10:00p SAN » 2:09a ORD
Spirit Airlines direct (4h09m)
inbound: Oct 1, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$167
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$169
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$170
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$170
outward: Dec 6, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$170
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 8, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$170
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 9, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$170
outward: Dec 7, 2018
10:45p SAN » 2:50a ORD
Spirit Airlines direct (4h05m)
inbound: Dec 10, 2018
5:30p ORD » 9:58p SAN
Spirit Airlines direct (4h28m)
$171
outward: Sep 25, 2018
7:44a SAN » 11:28a ORD
United Airlines direct (3h44m)
inbound: Sep 29, 2018
2:49p ORD » 7:06p SAN
United Airlines direct (4h17m)
$171
outward: Sep 26, 2018
12:32a SAN » 6:30a ORD
Spirit Airlines direct (5h58m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$171
outward: Sep 26, 2018
12:32a SAN » 6:30a ORD
Spirit Airlines direct (5h58m)
inbound: Oct 1, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$179
outward: Sep 25, 2018
5:16a SAN » 1:08p ORD
Spirit Airlines 1 stop (7h52m)
inbound: Oct 4, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$183
outward: Oct 18, 2018
10:00p SAN » 2:09a ORD
Spirit Airlines direct (4h09m)
inbound: Oct 21, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$188
outward: Sep 25, 2018
7:44a SAN » 11:28a ORD
United Airlines direct (3h44m)
inbound: Sep 29, 2018
2:49p ORD » 7:06p SAN
United Airlines direct (4h17m)
$188
outward: Sep 25, 2018
7:44a SAN » 11:28a ORD
United Airlines direct (3h44m)
inbound: Sep 29, 2018
2:49p ORD » 7:06p SAN
United Airlines direct (4h17m)
Return
Departure
29 September Sep Saturday $retDate.dayShortName
30 September Sep Sunday $retDate.dayShortName
01 October Oct Monday $retDate.dayShortName
02 October Oct Tuesday $retDate.dayShortName
03 October Oct Wednesday $retDate.dayShortName
04 October Oct Thursday $retDate.dayShortName
05 October Oct Friday $retDate.dayShortName
21 September Sep Friday $outDate.dayShortName
22 September Sep Saturday $outDate.dayShortName
23 September Sep Sunday $outDate.dayShortName
24 September Sep Monday $outDate.dayShortName
$164 $194 $200 $225 $216
25 September Sep Tuesday $outDate.dayShortName
$171 $178
26 September Sep Wednesday $outDate.dayShortName
$171 $196 $171 $189 $206
27 September Sep Thursday $outDate.dayShortName
$167 $192 $167
Choose when you'd like to depart to Chicago (USA):
Find the cheapest San Diego Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for San Diego - Chicago with these new dates, click on an offer. Want to depart from another city? Choose: Las Vegas - Chicago New York - Chicago London - Chicago Miami - Chicago San Francisco - Chicago See more routes

Airlines operating flights from San Diego to Chicago

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • all
  • Alaska Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Oct 9, 2018
Spirit Airlines direct
return: Oct 23, 2018
Spirit Airlines 1 stop
United Airlines
outbound: Oct 3, 2018
United Airlines direct
return: Oct 8, 2018
Frontier Airlines 1 stop
Alaska Airlines
outbound: Oct 3, 2018
Alaska Airlines 1 stop
return: Oct 8, 2018
Alaska Airlines direct

Travel tips for flights San Diego - Chicago

Average flight duration: 4h38m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 22, 2018 4:40 AM, GMT-5
  • Weather:
  • min. 55ºF, max. 67ºF
  • Departure city:
  • San Diego, USA
  • Airport(s):
  • Lindbergh Field (SAN)
  • Local time:
  • Sep 22, 2018 2:40 AM, GMT-7
  • Weather:
  • min. 66ºF, max. 74ºF