$123+ Cheap flights from Chicago (CHI) to San Diego (SAN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAN
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Diego with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to San Diego are usually found in February or January, booked 48 days in advance, depart on a Thursday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to San Diego
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Cheapest flights from Chicago to San DiegoExplore the most affordable flight options available from Chicago to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Chicago to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Travelocity deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:49 pm -
Nonstop4h 38m
Sat 10/246:25 am -
1 stop15h 59m
Deal found 9/19![Multiple Airlines logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am -
1 stop19h 27m
Sun 11/156:25 am -
1 stop15h 56m
Deal found 9/19![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:30 am -
1 stop11h 28m
Mon 10/265:46 pm -
Nonstop4h 13m
Deal found 9/18![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:30 pm -
1 stop6h 19m
Mon 10/268:34 pm -
2 stops25h 47m
Deal found 9/18![Frontier logo]()
$256
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:05 pm -
Nonstop4h 25m
Wed 10/2110:40 pm -
Nonstop3h 50m
Deal found 9/21![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:20 am -
Nonstop4h 36m
Tue 10/2712:35 pm -
Nonstop4h 18m
Deal found 9/21![Alaska Airlines logo]()
$257
This Frontier deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:30 am -
1 stop11h 38m
Mon 11/28:32 pm -
1 stop6h 41m
Deal found 9/19![Frontier logo]()
$258
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:30 pm -
1 stop27h 19m
Mon 10/192:01 pm -
1 stop8h 58m
Deal found 9/18![Frontier logo]()
$259
This Travelocity deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
Nonstop4h 43m
Tue 12/18:17 am -
1 stop18h 42m
Deal found 9/18![Multiple Airlines logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:30 am -
1 stop19h 26m
Mon 10/192:01 pm -
1 stop8h 58m
Deal found 9/21![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:30 pm -
1 stop6h 19m
Tue 10/276:25 am -
1 stop15h 56m
Deal found 9/19![Frontier logo]()
$262
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:55 am -
1 stop5h 50m
Sat 10/316:40 am -
Nonstop3h 50m
Deal found 9/19![Southwest logo]()
$263
Best flights from Chicago to San DiegoDiscover carefully curated flight deals from Chicago to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Chicago to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:20 am -
Nonstop4h 36m
Sat 10/177:00 am -
Nonstop4h 25m
Deal found 9/18![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:55 am -
1 stop5h 50m
Sat 10/316:40 am -
Nonstop3h 50m
Deal found 9/19![Southwest logo]()
$263
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:30 pm -
Nonstop4h 19m
Tue 10/207:41 pm -
1 stop7h 20m
Deal found 9/19![United Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:04 am -
1 stop7h 09m
Sat 11/712:38 pm -
1 stop7h 55m
Deal found 9/19![Delta logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:20 am -
Nonstop4h 36m
Wed 10/1412:35 pm -
Nonstop4h 18m
Deal found 9/18![Alaska Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:16 pm -
Nonstop4h 25m
Tue 10/276:50 am -
Nonstop4h 19m
Deal found 9/21![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:45 pm -
Nonstop4h 30m
Mon 12/74:05 pm -
Nonstop3h 50m
Deal found 9/19![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:20 am -
Nonstop4h 36m
Mon 10/265:46 pm -
Nonstop4h 13m
Deal found 9/19![Alaska Airlines logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:10 pm -
Nonstop4h 30m
Tue 10/274:45 pm -
1 stop6h 14m
Deal found 9/19![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:25 am -
Nonstop4h 25m
Mon 11/28:50 pm -
1 stop6h 10m
Deal found 9/18![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/92:13 pm -
Nonstop4h 38m
Tue 2/168:00 am -
Nonstop3h 54m
Deal found 9/21![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:45 pm -
1 stop6h 40m
Fri 10/2312:35 pm -
1 stop6h 00m
Deal found 9/21![Southwest logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:20 am -
Nonstop4h 36m
Wed 10/147:00 am -
Nonstop4h 25m
Deal found 9/18![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:55 am -
1 stop5h 50m
Sun 11/16:35 am -
Nonstop4h 00m
Deal found 9/19![Southwest logo]()
$303
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/77:40 am -
Nonstop4h 39m
Thu 1/147:00 am -
Nonstop4h 15m
Deal found 9/19![Alaska Airlines logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/192:54 pm -
Nonstop4h 25m
Tue 2/2312:45 pm -
Nonstop4h 10m
Deal found 9/19![Alaska Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:45 pm -
Nonstop4h 30m
Sun 12/610:35 pm -
1 stop6h 40m
Deal found 9/23![Southwest logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:57 pm -
Nonstop4h 46m
Mon 11/912:41 pm -
Nonstop4h 18m
Deal found 9/18![Alaska Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:05 am -
1 stop7h 40m
Sun 10/1810:40 pm -
Nonstop3h 50m
Deal found 9/20![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:20 pm -
2 stops7h 00m
Sat 11/2110:40 pm -
Nonstop3h 45m
Deal found 9/20![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:05 pm -
Nonstop4h 20m
Wed 10/710:40 pm -
Nonstop3h 50m
Deal found 9/18![Southwest logo]()
$375
Last-minute flights from Chicago to San DiegoDiscover last-minute flight deals from Chicago to San Diego. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Diego. Data last updated September 23, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:30 am -
1 stop19h 26m
Mon 10/192:01 pm -
1 stop8h 58m
Deal found 9/21![Frontier logo]()
$261
This Priceline deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:49 pm -
Nonstop4h 38m
Mon 10/192:01 pm -
1 stop8h 58m
Deal found 9/19![Multiple Airlines logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:30 pm -
1 stop27h 19m
Mon 10/192:01 pm -
1 stop8h 58m
Deal found 9/18![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:05 pm -
Nonstop4h 25m
Sat 10/246:30 am -
Nonstop3h 50m
Deal found 9/21![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:30 pm -
1 stop6h 19m
Mon 10/268:34 pm -
2 stops25h 47m
Deal found 9/18![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:30 pm -
1 stop6h 19m
Tue 10/276:25 am -
1 stop15h 56m
Deal found 9/19![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:30 am -
1 stop11h 28m
Mon 10/265:46 pm -
Nonstop4h 13m
Deal found 9/18![Multiple Airlines logo]()
$255
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:20 am -
Nonstop4h 36m
Tue 10/2712:35 pm -
Nonstop4h 18m
Deal found 9/21![Alaska Airlines logo]()
$257
This Travelocity deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:49 pm -
Nonstop4h 38m
Sat 10/246:25 am -
1 stop15h 59m
Deal found 9/19![Multiple Airlines logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
1 stop19h 26m
Mon 10/266:25 am -
1 stop15h 59m
Deal found 9/20![Frontier logo]()
$254
This Frontier deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:30 am -
1 stop11h 38m
Mon 11/28:32 pm -
1 stop6h 41m
Deal found 9/19![Frontier logo]()
$258
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:55 am -
1 stop5h 50m
Sat 10/316:40 am -
Nonstop3h 50m
Deal found 9/18![Southwest logo]()
$263
One-way flights from Chicago to San DiegoSearch for one-way flight options from Chicago to San Diego. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Chicago to San Diego. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:30 am -
1 stop19h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 am -
2 stops29h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:30 am -
1 stop11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$125
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 pm -
Nonstop4h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$128
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:55 pm -
Nonstop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$129
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:21 pm -
Nonstop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Alaska Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:30 am -
1 stop19h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$133
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:55 pm -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$134
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:32 pm -
1 stop8h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$134
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:15 pm -
2 stops27h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$135
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:30 am -
2 stops32h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:30 am -
1 stop19h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$137
Find flight deals from Chicago to San Diego
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Diego (SAN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Travelocity) |
One-way from | $123 (Cheapflightsfares) |
Popular in | August |
Cheapest in | February |
Average price | $348 |
Good round-trip deal | $290 or less |
Good one-way deal | $169 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Diego that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 23, 2026.
Use the filters below to find and compare flights from Chicago to San Diego that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Wed 11/18
3:45 pm-6:15 pm
Nonstop4h 30m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Sat 11/14
2:15 pm-4:56 pm
Nonstop4h 41m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Wed 11/18
2:15 pm-4:56 pm
Nonstop4h 41m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Tue 10/20
2:32 pm-8:45 pm
1 stop8h 13m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$134
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Wed 11/18
9:30 am-2:29 pm
1 stop6h 59m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Tue 11/17
6:00 am-1:08 pm
1 stop9h 08m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Tue 11/17
5:00 pm-10:10 pm
1 stop7h 10m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Thu 11/19
7:20 am-10:03 am
Nonstop4h 43m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Mon 11/16
2:15 pm-4:56 pm
Nonstop4h 41m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Tue 10/27
6:55 am-10:45 am
1 stop5h 50m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$144
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Chicago to San Diego
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Diego in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-San Diego flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Diego flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Diego flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San Diego flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Diego flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to San Diego
Have a flexible travel schedule? Discover the best time to fly to San Diego from Chicago with our price prediction graph.
CHI-SAN
ORD-SAN
MDW-SAN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to San Diego
CHI-SAN
ORD-SAN
MDW-SAN
What is the cheapest month to book a flight from Chicago to San Diego?
Currently, February is the cheapest month in which you can book a flight from Chicago to San Diego (average of $246). Flying from Chicago to San Diego in July is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to SAN?
Find hourly flight availability from Chicago to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego in the evening. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago to San Diego
Explore weekly flight availability from Chicago to San Diego. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 23, 2026.
The most flights from CHI to SAN are scheduled on a Monday (54 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (21 on average).
How much does it cost to fly round-trip from Chicago to San Diego?
Airfare is below average for this route at the moment.
Chicago to San Diego flights typically cost between $270 and $384 in October.The cheapest round-trip price found within the last 5 days was $253 on Multiple Airlines (Oct 22-Oct 24).
How far ahead should I book a flight from Chicago to San Diego?
Booking 47 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Diego. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to San Diego?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Diego. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to San Diego flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Diego trip
Our travel experts
Reviews of airlines servicing San Diego
Get insights into the airlines that provide service to San Diego. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Diego. Reviews last updated September 23, 2026.
Read through reviews of airlines operating flights from Chicago to San Diego, such as Southwest,Alaska Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Diego. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsEl Cajon
National City
Chula Vista
Coronado
San Ysidro
Poway
La Mesa
Santee
Julian
Lemon Grove
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Chicago and San Diego flights
Browse other Chicago and San Diego flight options. Last updated on September 23, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
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Top 7 airlines flying from Chicago to San Diego
Discover the top 7 airlines that operate flights from Chicago to San Diego. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$126 | Average$274 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$230 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$156 | Average$312 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$160 | Average$344 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$309 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$296 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$187 | Average$352 | FlexibilityNo cancel fee | On-time63% |