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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)
Verify
6 days ago
$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)
Verify
16 hours ago
$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)
Verify
20 hours ago
$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)
Verify
42 hours ago
$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)
Verify
41 hours ago
$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)
Verify
2 days ago
$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)
Verify
11 days ago
$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)
Verify
13 days ago
$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)
Verify
12 days ago
$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)
Verify
23 days ago
$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)
Verify
23 days ago
$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)
Verify
17 days ago
$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)
Verify
17 days ago
$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)
Verify
24 days ago
$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)
Verify
3 days ago
$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)
Verify
9 days ago
$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)
Verify
5 days ago
$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)
Verify
8 days ago
$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)
Verify
8 days ago
$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)
Verify
6 days ago
$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)
Verify
7 days ago
$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)
Verify
7 days ago
$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)
Verify
4 days ago
$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)
Verify
3 days ago
$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)
Verify
14 days ago
$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)
Verify
15 days ago
$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)
Verify
10 days ago
$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)
Verify
9 days ago
$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)
Verify
16 days ago
$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)
Verify
18 days ago
Return
Departure
Availability of fares is not guaranteed for offers found in the last 7 days.
Choose when you'd like to depart to Chicago (USA):
*Best price per person, all taxes and surcharges included; found in the last 14 days on liligo.com
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
$328 Verify
38 hours ago
Frontier Airlines
outbound: Jun 27, 2019
Frontier Airlines 1 stop
return: Jul 30, 2019
Spirit Airlines 1 stop
$432 Verify
38 hours ago
American Airlines
outbound: Jun 27, 2019
American Airlines direct
return: Jul 30, 2019
American Airlines direct
$740 Verify
38 hours ago
United Airlines
outbound: Jun 27, 2019
United Airlines direct
return: Jul 11, 2019
Delta Air Lines 1 stop
$661 Verify
4 days ago
Alaska Airlines
outbound: Jun 27, 2019
Alaska Airlines 1 stop
return: Jul 11, 2019
Alaska Airlines 1 stop
$899 Verify
4 days ago
Delta Air Lines
outbound: Aug 8, 2019
Delta Air Lines 1 stop
return: Aug 18, 2019
Spirit Airlines 1 stop
$326 Verify
25 days ago
Airline tickets San Diego - Chicago found in the last 30 days.

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
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