$140+ Cheap flights from San Diego (SAN) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Jul 14 — Jul 211
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Chicago 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 San Diego to Chicago are usually found in February or September, booked 44 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from San Diego to Chicago
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Best
Last-minute
One-way
Cheapest flights from San Diego to ChicagoExplore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 14, 2026.
Explore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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 8/2511:37 am
SAN
- ORD
1 stop10h 22m
Alaska Airlines
Tue 9/87:20 am
ORD
- SAN
Nonstop4h 40m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 8/710:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Tue 8/113:50 pm
MDW
- SAN
1 stop6h 40m
Southwest
Deal found 6/9![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 10/29:46 am
SAN
- ORD
1 stop6h 33m
Delta
Fri 10/96:30 pm
ORD
- SAN
1 stop6h 25m
Delta
Deal found 6/10![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 10/210:20 pm
SAN
- MDW
1 stop8h 47m
Delta
Fri 10/91:05 pm
MDW
- SAN
1 stop9h 13m
Delta
Deal found 6/10![Delta logo]()
$287
This CheapOair deal was found by Cheapflights users on 6/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:51 pm
SAN
- ORD
1 stop6h 46m
Frontier
Wed 7/299:57 pm
ORD
- SAN
1 stop27h 54m
Frontier
Deal found 6/11![Frontier logo]()
$288
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Sat 7/119:57 pm
ORD
- SAN
1 stop13h 08m
Frontier
Deal found 6/9![Frontier logo]()
$289
This Southwest deal was found by Cheapflights users on 6/9. 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 9/310:40 pm
SAN
- MDW
1 stop6h 30m
Southwest
Mon 9/76:15 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 6/9![Southwest logo]()
$289
This Trip.com deal was found by Cheapflights users on 6/9. 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.
Sun 6/149:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Tue 6/169:10 am
ORD
- SAN
1 stop11h 40m
Frontier
Deal found 6/9![Frontier logo]()
$290
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 10/11:03 pm
SAN
- ORD
Nonstop4h 18m
Alaska Airlines
Fri 10/97:49 pm
ORD
- SAN
Nonstop4h 38m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 6/10. 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 9/175:50 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Mon 9/215:00 pm
MDW
- SAN
2 stops7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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 8/11:21 pm
SAN
- ORD
Nonstop4h 16m
Alaska Airlines
Mon 8/107:59 pm
ORD
- SAN
Nonstop4h 34m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sun 8/24:12 pm
SAN
- RFD
1 stop26h 11m
Multiple Airlines
Wed 8/58:58 pm
RFD
- SAN
1 stop20h 45m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$292
Best flights from San Diego to ChicagoDiscover carefully curated flight deals from San Diego to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 14, 2026.
Discover carefully curated flight deals from San Diego to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Sun 8/305:45 pm
SAN
- ORD
Nonstop4h 14m
Alaska Airlines
Mon 8/316:00 am
ORD
- SAN
1 stop9h 19m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 6/10. 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 8/116:55 am
SAN
- MDW
Nonstop4h 00m
Southwest
Wed 8/1210:05 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 6/13. 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 8/204:08 pm
SAN
- ORD
Nonstop4h 06m
United Airlines
Sun 8/234:00 pm
ORD
- SAN
Nonstop4h 30m
United Airlines
Deal found 6/13![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 6/13. 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.
Fri 8/2110:17 pm
SAN
- MDW
1 stop9h 00m
Delta
Mon 8/247:25 pm
MDW
- SAN
1 stop6h 10m
Delta
Deal found 6/13![Delta logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 9/34:17 pm
SAN
- RFD
1 stop17h 02m
Multiple Airlines
Mon 9/71:39 pm
RFD
- SAN
1 stop27h 53m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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 8/57:00 am
SAN
- ORD
Nonstop4h 21m
Alaska Airlines
Mon 8/107:20 am
ORD
- SAN
1 stop8h 07m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 6/9. 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.
Mon 8/108:45 pm
SAN
- MDW
1 stop6h 15m
Southwest
Fri 8/148:45 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 6/9![Southwest logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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 10/275:43 pm
SAN
- ORD
Nonstop4h 16m
Alaska Airlines
Sat 10/312:21 pm
ORD
- SAN
Nonstop4h 40m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 6/13. 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 7/411:44 am
SAN
- ORD
1 stop7h 19m
United Airlines
Fri 7/108:46 am
ORD
- SAN
Nonstop4h 35m
United Airlines
Deal found 6/13![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 6/13. 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 8/226:15 pm
SAN
- MDW
1 stop8h 45m
Southwest
Tue 8/253:05 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 6/13![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 8/44:12 pm
SAN
- RFD
1 stop25h 56m
Multiple Airlines
Thu 8/61:24 pm
RFD
- SAN
1 stop8h 42m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 12/108:00 am
SAN
- ORD
Nonstop3h 54m
Alaska Airlines
Sat 1/92:54 pm
ORD
- SAN
Nonstop4h 25m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/214:12 pm
SAN
- RFD
1 stop25h 47m
Multiple Airlines
Sun 7/261:14 pm
RFD
- SAN
1 stop8h 52m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 6/10. 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 9/1710:10 am
SAN
- MDW
2 stops7h 10m
Southwest
Mon 9/215:00 pm
MDW
- SAN
2 stops7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 8/127:00 am
SAN
- ORD
Nonstop4h 21m
Alaska Airlines
Mon 8/248:17 pm
ORD
- SAN
Nonstop4h 43m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Fri 7/174:12 pm
SAN
- RFD
1 stop17h 56m
Multiple Airlines
Mon 7/209:13 pm
RFD
- SAN
1 stop20h 14m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 6/13. 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.
Fri 7/310:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 7/76:10 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 6/13![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Thu 11/1211:18 am
SAN
- RFD
1 stop6h 44m
Multiple Airlines
Sun 11/158:37 pm
RFD
- SAN
2 stops25h 00m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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.
Sun 7/267:00 am
SAN
- ORD
Nonstop4h 21m
Alaska Airlines
Wed 8/52:20 pm
ORD
- SAN
Nonstop4h 39m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 8/142:30 pm
SAN
- MDW
1 stop5h 50m
Southwest
Sun 8/166:10 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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 7/175:23 pm
SAN
- ORD
Nonstop4h 13m
Alaska Airlines
Fri 7/246:20 am
ORD
- SAN
Nonstop4h 34m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 6/12. 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 8/86:20 am
SAN
- MDW
2 stops8h 45m
Southwest
Wed 8/122:05 pm
MDW
- SAN
1 stop6h 15m
Southwest
Deal found 6/12![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 7/174:12 pm
SAN
- RFD
1 stop17h 56m
Multiple Airlines
Sun 8/21:14 pm
RFD
- SAN
1 stop8h 52m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 7/107:00 am
SAN
- ORD
Nonstop4h 21m
Alaska Airlines
Mon 7/137:59 pm
ORD
- SAN
Nonstop4h 34m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/12. 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 7/412:20 pm
SAN
- MDW
1 stop5h 50m
Southwest
Fri 7/109:10 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Deal found 6/12![Southwest logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/123:03 pm
SAN
- RFD
1 stop19h 31m
Multiple Airlines
Thu 8/209:35 pm
RFD
- SAN
2 stops13h 07m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Sun 8/94:28 pm
SAN
- RFD
1 stop26h 06m
Multiple Airlines
Sun 8/239:35 pm
RFD
- SAN
1 stop25h 23m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Sat 7/48:29 pm
SAN
- RFD
1 stop13h 55m
Multiple Airlines
Wed 7/88:49 pm
RFD
- SAN
1 stop20h 38m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sat 8/18:51 pm
SAN
- RFD
1 stop13h 33m
Multiple Airlines
Mon 8/39:13 pm
RFD
- SAN
1 stop20h 14m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$439
Last-minute flights from San Diego to ChicagoDiscover last-minute flight deals from San Diego to Chicago. Data last updated June 14, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chicago. Data last updated June 14, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Fri 7/39:48 pm
ORD
- SAN
1 stop12h 54m
Frontier
Deal found 6/10![Frontier logo]()
$293
This Trip.com deal was found by Cheapflights users on 6/9. 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.
Sun 6/149:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Tue 6/169:10 am
ORD
- SAN
1 stop11h 40m
Frontier
Deal found 6/9![Frontier logo]()
$290
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Sat 7/119:57 pm
ORD
- SAN
1 stop13h 08m
Frontier
Deal found 6/9![Frontier logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/73:03 pm
SAN
- ORD
1 stop12h 34m
Frontier
Tue 7/149:57 pm
ORD
- SAN
2 stops19h 46m
Frontier
Deal found 6/13![Frontier logo]()
$296
This Trip.com deal was found by Cheapflights users on 6/12. 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.
Mon 7/138:51 pm
SAN
- ORD
1 stop6h 46m
Multiple Airlines
Wed 7/156:20 am
ORD
- SAN
Nonstop4h 34m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Thu 7/234:12 pm
SAN
- RFD
1 stop26h 11m
Multiple Airlines
Wed 7/298:49 pm
RFD
- SAN
1 stop20h 38m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$295
This CheapOair deal was found by Cheapflights users on 6/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:51 pm
SAN
- ORD
1 stop6h 46m
Frontier
Wed 7/299:57 pm
ORD
- SAN
1 stop27h 54m
Frontier
Deal found 6/11![Frontier logo]()
$288
This lol.travel deal was found by Cheapflights users on 6/9. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:00 am
SAN
- ORD
Nonstop4h 21m
Alaska Airlines
Tue 8/47:59 pm
ORD
- SAN
Nonstop4h 34m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 6/10. 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 7/2810:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 8/258:25 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/293:03 pm
SAN
- ORD
1 stop12h 34m
Frontier
Tue 8/49:57 pm
ORD
- SAN
2 stops19h 48m
Frontier
Deal found 6/14![Frontier logo]()
$286
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 7/295:23 pm
SAN
- ORD
Nonstop4h 13m
Alaska Airlines
Mon 8/248:17 pm
ORD
- SAN
Nonstop4h 43m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$292
This Expedia deal was found by Cheapflights users on 6/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:03 pm
SAN
- ORD
1 stop12h 34m
Multiple Airlines
Tue 8/42:20 pm
ORD
- SAN
Nonstop4h 39m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$297
One-way flights from San Diego to ChicagoSearch for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated June 14, 2026.
Search for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated June 14, 2026.
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:43 am
SAN
- ORD
1 stop17h 24m
Frontier
Deal found 6/10![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 8/204:17 pm
SAN
- RFD
1 stop18h 06m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sun 9/207:24 pm
SAN
- RFD
1 stop22h 30m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$141
This Trip.com deal was found by Cheapflights users on 6/12. 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.
Tue 7/73:03 pm
SAN
- ORD
1 stop12h 34m
Frontier
Deal found 6/12![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 9/96:25 am
SAN
- MDW
2 stops27h 42m
Frontier
Deal found 6/11![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 9/29:53 pm
SAN
- RFD
1 stop20h 46m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$144
This Frontier deal was found by Cheapflights users on 6/13. 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.
Wed 8/126:35 am
SAN
- ORD
1 stop7h 25m
Frontier
Deal found 6/13![Frontier logo]()
$145
This Frontier deal was found by Cheapflights users on 6/13. 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.
Tue 8/116:35 am
SAN
- MDW
1 stop8h 16m
Frontier
Deal found 6/13![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/176:25 am
SAN
- ORD
1 stop12h 27m
Frontier
Deal found 6/12![Frontier logo]()
$146
This Delta deal was found by Cheapflights users on 6/9. 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.
Thu 8/610:17 pm
SAN
- ORD
1 stop7h 39m
Delta
Deal found 6/9![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 6/9. 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.
Fri 8/710:25 pm
SAN
- MDW
1 stop9h 45m
Delta
Deal found 6/9![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 8/83:00 pm
SAN
- ORD
1 stop6h 48m
Delta
Deal found 6/9![Delta logo]()
$148
Find flight deals from San Diego to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Chicago (CHI). 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 June 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $286 (Alaska Airlines) |
One-way from | $140 (Super.com) |
Popular in | June |
Cheapest in | February |
Average price | $348 |
Good round-trip deal | $361 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Chicago 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 2,558,603 searches. Data last updated June 14, 2026.
Use the filters below to find and compare flights from San Diego to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sun 8/30
5:45 pm-11:59 pm
Nonstop4h 14m
Chicago O'Hare Intl
Mon 8/31
6:00 am-1:19 pm
1 stop9h 19m
$286
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 8/5
7:00 am-1:21 pm
Nonstop4h 21m
Chicago O'Hare Intl
Mon 8/10
7:20 am-1:27 pm
1 stop8h 07m
$286
Quickest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 8/11
6:55 am-12:55 pm
Nonstop4h 00m
Chicago Midway
Wed 8/12
10:05 am-12:15 pm
Nonstop4h 10m
$292
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 8/20
4:08 pm-10:14 pm
Nonstop4h 06m
Chicago O'Hare Intl
Sun 8/23
4:00 pm-6:30 pm
Nonstop4h 30m
$307
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 10/27
5:43 pm-11:59 pm
Nonstop4h 16m
Chicago O'Hare Intl
Sat 10/31
2:21 pm-5:01 pm
Nonstop4h 40m
$307
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Mon 8/10
8:45 pm-5:00 am
1 stop6h 15m
Chicago Midway
Fri 8/14
8:45 pm-10:55 pm
Nonstop4h 10m
$310
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 12/10
8:00 am-1:54 pm
Nonstop3h 54m
Chicago O'Hare Intl
Sat 1/9
2:54 pm-5:19 pm
Nonstop4h 25m
$316
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 8/22
6:15 pm-5:00 am
1 stop8h 45m
Chicago Midway
Tue 8/25
3:05 pm-5:10 pm
Nonstop4h 05m
$317
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 8/12
7:00 am-1:21 pm
Nonstop4h 21m
Chicago O'Hare Intl
Mon 8/24
8:17 pm-11:00 pm
Nonstop4h 43m
$321
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 8/21
10:17 pm-9:17 am
1 stop9h 00m
Chicago Midway
Mon 8/24
7:25 pm-11:35 pm
1 stop6h 10m
$327
Showing 1-10 of 59 resultsSorted by cheapest first
Compare providers for flights from San Diego to Chicago
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 San Diego to Chicago in June.
| 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 Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Diego-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Diego-Chicago 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 San Diego-Chicago 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 San Diego to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Diego with our price prediction graph.
SAN-CHI
SAN-ORD
SAN-MDW
SAN-RFD
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 San Diego to Chicago
SAN-CHI
SAN-ORD
SAN-MDW
SAN-RFD
What is the cheapest month to book a flight from San Diego to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $91). Flying from San Diego to Chicago in April is currently the most expensive (average of $741). 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 SAN to CHI?
Find hourly flight availability from San Diego to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 14, 2026.
It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from San Diego to Chicago
Explore weekly flight availability from San Diego to Chicago. 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 June 14, 2026.
The most flights from SAN to CHI are scheduled on a Friday (57 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from San Diego to Chicago?
How often are flights from San Diego to Chicago delayed?
About 10% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 181 minutes.
What is the most punctual flight time for San Diego to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Diego to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
How far ahead should I book a flight from San Diego to Chicago?
The price you pay for your flight from San Diego to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from San Diego to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Diego to Chicago. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for San Diego to Chicago 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 San Diego to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 14, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andUnited Airlines from San Diego to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Entertainment
7.0
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from San Diego to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 14, 2026.
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San Diego and Chicago flights
Browse other San Diego and Chicago flight options. Last updated on June 14, 2026.
Other flights from San Diego
Browse through other flights departing from San Diego. Flights are based on user searches made on Cheapflights and were last updated on June 14, 2026.
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Top 6 airlines flying from San Diego to Chicago
Discover the top 6 airlines that operate flights from San Diego to Chicago. 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 2,558,603 searches. Data last updated June 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$241 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$197 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$155 | Average$315 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$157 | Average$323 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$163 | Average$350 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$205 | Average$359 | FlexibilityNo cancel fee | On-time63% |