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
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • any
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • price
  • month of departure
  • month of return
$202
Spirit Airlines outward: Sep 11, 2019
3:20p SAN » 10:34p ORD
Spirit Airlines 1 stop (7h14m)
Spirit Airlines inbound: Sep 12, 2019
4:50a ORD » 11:53p SAN
Spirit Airlines 1 stop (19h03m)
$203
Southwest Airlines outward: Jul 27, 2019
4:00a SAN » 7:50a MDW
Southwest Airlines direct (3h50m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$223
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$223
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$223
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$224
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$236
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$237
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$237
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$237
Spirit Airlines outward: Jul 10, 2019
10:55p SAN » 3:08a ORD
Spirit Airlines direct (4h13m)
Spirit Airlines inbound: Jul 13, 2019
5:33p ORD » 10:00p SAN
Spirit Airlines direct (4h27m)
$237
Spirit Airlines outward: Jul 10, 2019
10:55p SAN » 3:08a ORD
Spirit Airlines direct (4h13m)
Spirit Airlines inbound: Jul 13, 2019
5:33p ORD » 10:00p SAN
Spirit Airlines direct (4h27m)
$238
Spirit Airlines outward: Jul 19, 2019
5:05a SAN » 1:50p ORD
Spirit Airlines 1 stop (8h45m)
Spirit Airlines inbound: Jul 27, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$238
Spirit Airlines outward: Jul 19, 2019
5:05a SAN » 1:50p ORD
Spirit Airlines 1 stop (8h45m)
Spirit Airlines inbound: Jul 27, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$238
Spirit Airlines outward: Jul 10, 2019
10:55p SAN » 3:08a ORD
Spirit Airlines direct (4h13m)
Spirit Airlines inbound: Jul 13, 2019
5:33p ORD » 10:00p SAN
Spirit Airlines direct (4h27m)
$238
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$238
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$239
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$239
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$239
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$239
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$239
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$239
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
3:20p ORD » 11:37p SAN
Spirit Airlines 1 stop (8h17m)
$239
Spirit Airlines outward: Aug 9, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Aug 13, 2019
10:20p ORD » 8:23a SAN
Spirit Airlines 1 stop (10h03m)
$246
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$249
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$249
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$250
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$250
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$250
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
$251
Spirit Airlines outward: Jul 26, 2019
10:49p SAN » 3:03a ORD
Spirit Airlines direct (4h14m)
Spirit Airlines inbound: Jul 30, 2019
5:36p ORD » 9:54p SAN
Spirit Airlines direct (4h18m)
Return
Departure
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:

Airlines operating flights from San Diego to Chicago

  • any
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • all
  • Alaska Airlines
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jun 27, 2019
Spirit Airlines direct
return: Jul 30, 2019
Spirit Airlines direct
Frontier Airlines
outbound: Jun 27, 2019
Frontier Airlines 1 stop
return: Jul 30, 2019
Spirit Airlines 1 stop
American Airlines
outbound: Jun 27, 2019
American Airlines direct
return: Jul 30, 2019
American Airlines direct
United Airlines
outbound: Jun 27, 2019
United Airlines direct
return: Jul 11, 2019
Delta Air Lines 1 stop
Alaska Airlines
outbound: Jun 27, 2019
Alaska Airlines 1 stop
return: Jul 11, 2019
Alaska Airlines 1 stop
Delta Air Lines
outbound: Aug 8, 2019
Delta Air Lines 1 stop
return: Aug 18, 2019
Spirit Airlines 1 stop

Travel tips for flights San Diego - Chicago

Average flight duration: 4h13m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 24, 2019 4:52 AM, GMT-5
  • Weather:
  • min. 64ºF, max. 75ºF
  • Departure city:
  • San Diego, USA
  • Airport(s):
  • Lindbergh Field (SAN)
  • Local time:
  • Jun 24, 2019 2:52 AM, GMT-7
  • Weather:
  • min. 64ºF, max. 71ºF