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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$142
outward: Sep 25, 2018
5:16a SAN » 1:08p ORD
Spirit Airlines 1 stop (7h52m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$142
outward: Sep 25, 2018
5:16a SAN » 1:08p ORD
Spirit Airlines 1 stop (7h52m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$155
outward: Aug 9, 2018
5:05a SAN » 1:24p ORD
Spirit Airlines 1 stop (8h19m)
inbound: Aug 15, 2018
3:15p ORD » 11:38p SAN
Spirit Airlines 1 stop (8h23m)
$159
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)
$165
outward: Aug 9, 2018
5:05a SAN » 1:24p ORD
Spirit Airlines 1 stop (8h19m)
inbound: Aug 14, 2018
3:15p ORD » 11:38p SAN
Spirit Airlines 1 stop (8h23m)
$169
outward: Aug 8, 2018
5:05a SAN » 1:24p ORD
Spirit Airlines 1 stop (8h19m)
inbound: Aug 11, 2018
3:15p ORD » 11:38p SAN
Spirit Airlines 1 stop (8h23m)
$170
outward: Sep 25, 2018
1:09a SAN » 7:56a ORD
American Airlines 1 stop (6h47m)
inbound: Sep 29, 2018
12:15p ORD » 7:41p SAN
American Airlines 1 stop (7h26m)
$177
outward: Sep 6, 2018
9:50p SAN » 1:45a MKE
Frontier Airlines direct (3h55m)
inbound: Sep 11, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$177
outward: Sep 6, 2018
9:50p SAN » 1:45a MKE
Frontier Airlines direct (3h55m)
inbound: Sep 11, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$178
outward: Sep 6, 2018
9:50p SAN » 1:45a MKE
Frontier Airlines direct (3h55m)
inbound: Sep 11, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$178
outward: Sep 6, 2018
9:50p SAN » 1:45a MKE
Frontier Airlines direct (3h55m)
inbound: Sep 11, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$179
outward: Sep 25, 2018
5:16a SAN » 1:08p ORD
Spirit Airlines 1 stop (7h52m)
inbound: Sep 29, 2018
4:45p ORD » 9:12p SAN
Spirit Airlines direct (4h27m)
$180
outward: Aug 7, 2018
5:05a SAN » 1:24p ORD
Spirit Airlines 1 stop (8h19m)
inbound: Aug 7, 2018
5:25p ORD » 9:35p SAN
Spirit Airlines direct (4h10m)
$183
outward: Aug 29, 2018
10:27p SAN » 2:30a ORD
Spirit Airlines direct (4h03m)
inbound: Sep 4, 2018
5:21p ORD » 9:32p SAN
Spirit Airlines direct (4h11m)
$184
outward: Aug 14, 2018
10:30p SAN » 2:34a ORD
Spirit Airlines direct (4h04m)
inbound: Sep 5, 2018
5:21p ORD » 9:32p SAN
Spirit Airlines direct (4h11m)
$184
outward: Aug 15, 2018
10:30p SAN » 2:34a ORD
Spirit Airlines direct (4h04m)
inbound: Sep 5, 2018
5:21p ORD » 9:32p SAN
Spirit Airlines direct (4h11m)
$186
outward: Aug 9, 2018
12:40a SAN » 6:43a ORD
Frontier Airlines 1 stop (6h03m)
inbound: Aug 14, 2018
3:15p ORD » 11:38p SAN
Spirit Airlines 1 stop (8h23m)
$188
outward: Sep 6, 2018
9:50p SAN » 1:45a MKE
Frontier Airlines direct (3h55m)
inbound: Sep 11, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$190
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$190
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$190
outward: Sep 14, 2018
3:30p SAN » 10:34p ORD
Spirit Airlines 1 stop (7h04m)
inbound: Sep 17, 2018
7:35p ORD » 7:57a SAN
Spirit Airlines 1 stop (12h22m)
$191
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)
$191
outward: Sep 14, 2018
3:30p SAN » 11:27p ORD
Spirit Airlines 1 stop (7h57m)
inbound: Sep 17, 2018
7:35p ORD » 7:57a SAN
Spirit Airlines 1 stop (12h22m)
$191
outward: Sep 14, 2018
3:30p SAN » 11:27p ORD
Spirit Airlines 1 stop (7h57m)
inbound: Sep 17, 2018
7:35p ORD » 7:57a SAN
Spirit Airlines 1 stop (12h22m)
$191
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$191
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$191
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$191
outward: Sep 12, 2018
11:15p SAN » 7:04a MKE
Frontier Airlines 1 stop (7h49m)
inbound: Sep 25, 2018
5:55p MKE » 10:15p SAN
Frontier Airlines direct (4h20m)
$195
outward: Aug 14, 2018
10:30p SAN » 2:34a ORD
Spirit Airlines direct (4h04m)
inbound: Sep 4, 2018
5:21p ORD » 9:32p SAN
Spirit Airlines direct (4h11m)
$195
outward: Aug 15, 2018
10:30p SAN » 2:34a ORD
Spirit Airlines direct (4h04m)
inbound: Sep 4, 2018
5:21p ORD » 9:32p SAN
Spirit Airlines direct (4h11m)
Return
Departure
28 July Jul Saturday $retDate.dayShortName
29 July Jul Sunday $retDate.dayShortName
30 July Jul Monday $retDate.dayShortName
31 July Jul Tuesday $retDate.dayShortName
01 August Aug Wednesday $retDate.dayShortName
02 August Aug Thursday $retDate.dayShortName
03 August Aug Friday $retDate.dayShortName
23 July Jul Monday $outDate.dayShortName
$244 $264 $258 $274
24 July Jul Tuesday $outDate.dayShortName
$264 $259 $248 $244 $253 $236
25 July Jul Wednesday $outDate.dayShortName
$214 $259 $243 $232 $252
26 July Jul Thursday $outDate.dayShortName
$232 $268 $243 $197 $232 $221 $241
27 July Jul Friday $outDate.dayShortName
$252 $263 $250 $250 $241 $261
28 July Jul Saturday $outDate.dayShortName
29 July Jul Sunday $outDate.dayShortName
$318 $242 $239 $239
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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • all
  • Alaska Airlines
  • American Airlines
  • Frontier Airlines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 8, 2018
Spirit Airlines 1 stop
return: Aug 15, 2018
Spirit Airlines 1 stop
Southwest Airlines
outbound: Dec 22, 2018
Southwest Airlines direct
return: Dec 29, 2018
Southwest Airlines direct
JetBlue
outbound: Sep 24, 2018
JetBlue 1 stop
return: Sep 29, 2018
Spirit Airlines 1 stop
United Airlines
outbound: Sep 18, 2018
United Airlines direct
return: Sep 25, 2018
Spirit Airlines 1 stop
Alaska Airlines
outbound: Sep 18, 2018
Alaska Airlines 2 stops
return: Sep 25, 2018
Alaska Airlines 2 stops
Frontier Airlines
outbound: Sep 26, 2018
Frontier Airlines 1 stop
return: Sep 30, 2018
Spirit Airlines direct
American Airlines
outbound: Sep 21, 2018
American Airlines direct
return: Sep 23, 2018
American Airlines 1 stop

Travel tips for flights San Diego - Chicago

Average flight duration: 4h34m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 15, 2018 6:03 PM, GMT-5
  • Weather:
  • min. 66ºF, max. 77ºF
  • Departure city:
  • San Diego, USA
  • Airport(s):
  • Lindbergh Field (SAN)
  • Local time:
  • Jul 15, 2018 4:03 PM, GMT-7
  • Weather:
  • min. 67ºF, max. 73ºF