$122+ Cheap flights from San Diego (SAN) to Chicago (CHI)
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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Oct 10 — Oct 171
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 January, booked 44 days in advance, depart on a Wednesday or Friday and return on a Wednesday
Cheap flight deals from San Diego to Chicago
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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 September 10, 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 September 10, 2026.
This Frontier deal was found by Cheapflights users on 9/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:54 pm -
1 stop9h 44m
Wed 9/306:30 am -
1 stop11h 29m
Deal found 9/9![Frontier logo]()
$247
This CheapOair deal was found by Cheapflights users on 9/8. 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.
Wed 10/286:25 am -
1 stop15h 56m
Mon 11/26:30 am -
1 stop11h 38m
Deal found 9/8![Frontier logo]()
$248
This Expedia deal was found by Cheapflights users on 9/9. 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.
Fri 10/236:25 am -
1 stop15h 59m
Mon 10/266:30 am -
1 stop19h 26m
Deal found 9/9![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/214:53 pm -
1 stop29h 31m
Mon 10/264:20 pm -
1 stop19h 51m
Deal found 9/8![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/106:25 am -
1 stop15h 59m
Sat 10/176:30 am -
1 stop11h 28m
Deal found 9/6![Frontier logo]()
$251
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:01 pm -
1 stop8h 58m
Mon 10/197:49 pm -
Nonstop4h 38m
Deal found 9/9![Multiple Airlines logo]()
$252
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:54 pm -
1 stop9h 23m
Wed 10/147:20 am -
Nonstop4h 36m
Deal found 9/9![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/146:25 am -
1 stop15h 59m
Mon 10/194:20 pm -
1 stop24h 09m
Deal found 9/8![Frontier logo]()
$254
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/246:25 am -
1 stop15h 59m
Sat 10/316:30 am -
1 stop19h 27m
Deal found 9/9![Frontier logo]()
$255
This Trip.com deal was found by Cheapflights users on 9/8. 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.
Wed 10/77:00 am -
Nonstop4h 25m
Wed 10/147:20 am -
Nonstop4h 36m
Deal found 9/8![Alaska Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Wed 10/710:40 pm -
Nonstop4h 09m
Wed 10/147:00 pm -
Nonstop4h 34m
Deal found 9/8![American Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/36:30 am -
Nonstop3h 50m
Sat 10/103:05 pm -
Nonstop4h 20m
Deal found 9/9![Southwest logo]()
$257
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 September 10, 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 September 10, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 10/247:00 am -
Nonstop4h 25m
Sat 10/317:20 am -
Nonstop4h 36m
Deal found 9/9![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/710:40 pm -
Nonstop3h 50m
Wed 10/146:25 am -
Nonstop4h 25m
Deal found 9/9![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 9/5. 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.
Tue 10/1311:02 am -
1 stop10h 32m
Mon 10/196:35 am -
1 stop8h 23m
Deal found 9/5![Delta logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/153:14 pm -
2 stops18h 13m
Sun 10/189:33 pm -
1 stop24h 16m
Deal found 9/8![Multiple Airlines logo]()
$309
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 10/37:00 am -
Nonstop4h 25m
Thu 10/157:20 am -
Nonstop4h 36m
Deal found 9/9![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/6. 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 2/2210:40 pm -
Nonstop3h 50m
Thu 2/252:20 pm -
Nonstop4h 20m
Deal found 9/6![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/5. 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 10/3111:02 am -
1 stop10h 52m
Sun 11/86:35 am -
1 stop8h 23m
Deal found 9/5![Delta logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/15:45 pm -
Nonstop4h 14m
Sat 10/319:00 am -
1 stop28h 13m
Deal found 9/7![Alaska Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 9/7. 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 10/2911:02 am -
1 stop10h 32m
Sun 11/16:35 am -
1 stop8h 23m
Deal found 9/7![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 9/6. 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 9/2911:05 am -
1 stop6h 15m
Wed 9/308:25 pm -
Nonstop4h 15m
Deal found 9/6![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/37:33 pm -
1 stop14h 50m
Wed 11/111:13 pm -
1 stop22h 58m
Deal found 9/7![Multiple Airlines logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 11/215:32 pm -
Nonstop4h 17m
Thu 11/267:26 am -
Nonstop4h 41m
Deal found 9/6![Alaska Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/6. 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 9/2810:40 pm -
1 stop6h 55m
Mon 10/59:25 pm -
Nonstop4h 25m
Deal found 9/6![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 11/1811:32 am -
1 stop10h 27m
Mon 11/237:57 pm -
Nonstop4h 55m
Deal found 9/8![Alaska Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/1710:40 pm -
1 stop6h 15m
Thu 10/225:25 am -
Nonstop4h 25m
Deal found 9/9![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/277:33 pm -
1 stop15h 44m
Mon 11/212:27 pm -
1 stop23h 44m
Deal found 9/6![Multiple Airlines logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 9/307:03 am -
Nonstop4h 19m
Tue 10/67:00 am -
1 stop12h 52m
Deal found 9/6![Alaska Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/8. 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 10/14:50 pm -
1 stop6h 15m
Mon 10/59:25 pm -
Nonstop4h 25m
Deal found 9/8![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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.
Mon 9/285:45 pm -
Nonstop4h 14m
Mon 10/57:16 pm -
1 stop16h 50m
Deal found 9/7![Alaska Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/202:01 pm -
1 stop21h 16m
Fri 10/237:56 pm -
2 stops38h 53m
Deal found 9/5![Multiple Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 9/6. 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 11/910:40 pm -
Nonstop3h 45m
Fri 11/137:50 am -
1 stop7h 15m
Deal found 9/6![Southwest logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 10/268:28 pm -
1 stop18h 22m
Tue 11/37:20 am -
Nonstop4h 43m
Deal found 9/6![Alaska Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 9/5. 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 10/1910:15 pm -
1 stop5h 30m
Fri 10/239:25 pm -
Nonstop4h 25m
Deal found 9/5![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/46:54 pm -
1 stop16h 13m
Sun 10/119:33 pm -
1 stop24h 16m
Deal found 9/6![Multiple Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 9/8. 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 10/169:10 pm -
1 stop6h 30m
Mon 10/195:15 am -
1 stop6h 05m
Deal found 9/8![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 9/7. 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 10/2910:40 pm -
Nonstop3h 50m
Sun 11/19:20 pm -
Nonstop4h 25m
Deal found 9/7![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/212:01 pm -
2 stops27h 29m
Mon 10/261:27 pm -
1 stop22h 44m
Deal found 9/8![Multiple Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 9/9. 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 11/510:40 pm -
Nonstop3h 45m
Sun 11/89:20 pm -
Nonstop4h 25m
Deal found 9/9![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/82:01 pm -
1 stop19h 26m
Sun 10/119:33 pm -
2 stops17h 43m
Deal found 9/5![Multiple Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sun 11/85:20 pm -
1 stop5h 45m
Wed 11/1110:55 am -
1 stop7h 25m
Deal found 9/9![Southwest logo]()
$317
Last-minute flights from San Diego to ChicagoDiscover last-minute flight deals from San Diego to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chicago. Data last updated September 10, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/8. 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.
Tue 9/156:25 am -
1 stop15h 58m
Wed 9/166:30 am -
1 stop11h 29m
Deal found 9/8![Frontier logo]()
$288
This Priceline deal was found by Cheapflights users on 9/8. 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.
Fri 9/189:03 pm -
1 stop6h 35m
Wed 10/147:20 am -
Nonstop4h 36m
Deal found 9/8![Multiple Airlines logo]()
$287
This Expedia deal was found by Cheapflights users on 9/5. 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.
Sat 9/196:25 am -
1 stop15h 58m
Tue 9/226:30 am -
1 stop11h 29m
Deal found 9/5![Frontier logo]()
$276
This Southwest deal was found by Cheapflights users on 9/7. 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 9/2810:40 pm -
Nonstop3h 50m
Mon 10/59:25 pm -
Nonstop4h 25m
Deal found 9/7![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/36:30 am -
Nonstop3h 50m
Sat 10/37:05 pm -
Nonstop4h 20m
Deal found 9/9![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/33:35 pm -
1 stop6h 35m
Sat 10/107:05 pm -
Nonstop4h 25m
Deal found 9/9![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 9/6. 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 10/310:40 pm -
Nonstop3h 50m
Tue 10/64:45 pm -
1 stop6h 40m
Deal found 9/6![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/8. 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 10/610:40 pm -
Nonstop3h 50m
Fri 10/99:25 pm -
Nonstop4h 25m
Deal found 9/8![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 9/7. 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 10/1310:40 pm -
Nonstop3h 50m
Mon 10/195:15 am -
1 stop6h 05m
Deal found 9/7![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 9/8. 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 10/1410:40 pm -
Nonstop3h 50m
Tue 10/274:35 pm -
1 stop5h 50m
Deal found 9/8![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/1410:40 pm -
Nonstop3h 50m
Mon 10/195:15 am -
1 stop6h 05m
Deal found 9/9![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/2810:40 pm -
Nonstop3h 50m
Fri 10/305:15 am -
1 stop6h 05m
Deal found 9/10![Southwest logo]()
$284
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 September 10, 2026.
Search for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/193:14 pm -
2 stops13h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:25 am -
1 stop15h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$123
This Booking.com deal was found by Cheapflights users on 9/8. 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.
Wed 11/46:25 am -
1 stop15h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$124
This Expedia deal was found by Cheapflights users on 9/9. 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.
Tue 10/66:25 am -
1 stop15h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 9/9. 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.
Tue 10/206:25 am -
1 stop15h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$126
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:46 pm -
Nonstop4h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 9/8. 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 10/610:40 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$129
This Booking.com deal was found by Cheapflights users on 9/8. 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.
Fri 10/98:34 pm -
1 stop6h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/26:54 pm -
1 stop23h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 12/83:44 pm -
1 stop21h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$135
This Super.com deal was found by Cheapflights users on 9/6. 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.
Sat 9/269:03 am -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$137
This Southwest deal was found by Cheapflights users on 9/7. 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 10/56:45 pm -
Nonstop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$139
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Frontier) |
One-way from | $122 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $309 |
Good round-trip deal | $332 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 7,457,451 searches. Data last updated September 10, 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 San Diego - RFD Chicago Greater Rockford
SANRFD
San Diego
Fri 10/2
6:54 pm-8:08 pm
1 stop23h 14m
Chicago Greater Rockford
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Thu 3/4
8:00 am-1:54 pm
Nonstop3h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Sat 9/26
7:32 am-1:59 pm
Nonstop4h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
Quickest round-trip
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sat 3/6
10:45 am-4:35 pm
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Mon 11/2
5:35 pm-11:49 pm
Nonstop4h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sat 11/7
5:00 pm-10:50 pm
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Sat 11/7
12:41 pm-6:59 pm
Nonstop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Mon 9/28
10:40 pm-4:30 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Tue 11/3
7:02 am-1:17 pm
Nonstop4h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 1/5
6:30 am-12:30 pm
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$139
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 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | 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-MDW
SAN-ORD
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-MDW
SAN-ORD
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 $246). Flying from San Diego to Chicago in July is currently the most expensive (average of $384). 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 September 10, 2026.
It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight at noon.
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 September 10, 2026.
The most flights from SAN to CHI are scheduled on a Tuesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from San Diego to Chicago?
Airfare is below average for this route at the moment.
San Diego to Chicago flights typically cost between $265 and $402 in September.The cheapest round-trip price found within the last 5 days was $247 on Frontier (Sep 22-Sep 30).
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 186 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?
Thursday 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 62 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 September 5, 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. Saturday 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 September 10, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 September 10, 2026.
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San Diego and Chicago flights
Browse other San Diego and Chicago flight options. Last updated on September 10, 2026.
Other flights from San Diego
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Top 5 airlines flying from San Diego to Chicago
Discover the top 5 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$279 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$324 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$167 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$370 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$386 | FlexibilityNo cancel fee | On-time63% |