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Find cheap airline tickets from San Diego to Chicago by date

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  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • any
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • price
  • month of departure
  • month of return
$377
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 1:20p ORD
Spirit Airlines 1 stop (17h56m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
3 days ago
$377
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 1:20p ORD
Spirit Airlines 1 stop (17h56m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
4 days ago
$382
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
9 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
11 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
10 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
12 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
15 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
16 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
13 days ago
$384
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
14 days ago
$408
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 1:20p ORD
Spirit Airlines 1 stop (17h56m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
6 days ago
$409
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 1:20p ORD
Spirit Airlines 1 stop (17h56m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
7 days ago
$411
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
2:45p ORD » 6:32p SAN
Spirit Airlines 1 stop (27h47m)
Verify
8 days ago
$412
Spirit Airlines outward: Dec 21, 2019
10:45p SAN » 2:45a ORD
Spirit Airlines direct (4h)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
20 hours ago
$413
Spirit Airlines outward: Dec 21, 2019
10:45p SAN » 2:45a ORD
Spirit Airlines direct (4h)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
44 hours ago
$414
Spirit Airlines outward: Dec 21, 2019
10:45p SAN » 2:45a ORD
Spirit Airlines direct (4h)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
2 days ago
$414
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
21 days ago
$415
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
20 days ago
$415
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
26 days ago
$416
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
19 days ago
$416
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
17 days ago
$416
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
18 days ago
$446
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
23 days ago
$446
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
22 days ago
$447
Spirit Airlines outward: Dec 21, 2019
4:06p SAN » 7:55a ORD
Spirit Airlines 1 stop (15h49m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
25 days ago
$478
Spirit Airlines outward: Dec 21, 2019
7:24p SAN » 7:55a ORD
Spirit Airlines 1 stop (12h31m)
Spirit Airlines inbound: Jan 4, 2020
5:25p ORD » 10:00p SAN
Spirit Airlines direct (4h35m)
Verify
24 days ago
$935
Delta Air Lines outward: Dec 22, 2019
7:25a SAN » 4:12p MDW
Delta Air Lines 1 stop (8h47m)
Delta Air Lines inbound: Jan 4, 2020
10:00p ORD » 6:38a SAN
Delta Air Lines 1 stop (8h38m)
Verify
5 days ago
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Departure
Availability of fares is not guaranteed for offers found in the last 7 days.
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

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Travel tips for flights San Diego - Chicago

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 13, 2019 7:42 AM, GMT-6
  • Weather:
  • min. 31ºF, max. 38ºF
  • Departure city:
  • San Diego, USA
  • Airport(s):
  • Lindbergh Field (SAN)
  • Local time:
  • Dec 13, 2019 5:42 AM, GMT-8
  • Weather:
  • min. 60ºF, max. 66ºF
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