$132+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Nov 27 — Dec 41
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 Thursday or Wednesday and return on a Thursday
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 October 28, 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 October 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/139:32 am -
1 stop7h 43m
Sat 11/146:30 am -
1 stop11h 28m
Deal found 10/25![Frontier logo]()
$259
This Mytrip deal was found by Cheapflights users on 10/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:20 pm -
1 stop6h 53m
Mon 11/2312:05 pm -
2 stops21h 50m
Deal found 10/23![Frontier logo]()
$260
This Mytrip deal was found by Cheapflights users on 10/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:38 pm -
2 stops26h 43m
Sun 11/156:30 am -
1 stop11h 38m
Deal found 10/23![Frontier logo]()
$261
This CheapOair deal was found by Cheapflights users on 10/25. 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.
Thu 11/128:20 pm -
1 stop6h 53m
Sun 11/155:15 pm -
1 stop28h 20m
Deal found 10/25![Frontier logo]()
$262
This Southwest deal was found by Cheapflights users on 10/25. 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 11/108:20 am -
2 stops7h 05m
Sun 11/159:20 pm -
Nonstop4h 30m
Deal found 10/25![Southwest logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/106:25 am -
2 stops14h 48m
Sun 11/156:30 am -
1 stop11h 38m
Deal found 10/25![Frontier logo]()
$263
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Wed 12/169:58 am -
2 stops12h 56m
Sun 12/205:58 am -
2 stops20h 00m
Deal found 10/27![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/212:45 pm -
2 stops14h 57m
Tue 1/57:30 am -
1 stop7h 04m
Deal found 10/26![Frontier logo]()
$265
This Southwest deal was found by Cheapflights users on 10/23. 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.
Wed 12/163:15 pm -
1 stop7h 00m
Fri 12/186:00 am -
Nonstop4h 30m
Deal found 10/23![Southwest logo]()
$265
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/2410:45 pm -
Nonstop4h 05m
Tue 12/16:45 am -
Nonstop4h 49m
Deal found 10/27![American Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 10/26. 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 12/104:05 pm -
Nonstop3h 55m
Thu 12/179:20 pm -
Nonstop4h 30m
Deal found 10/26![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 10/27. 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 11/1310:30 pm -
1 stop8h 52m
Sun 11/227:17 pm -
1 stop6h 36m
Deal found 10/27![Delta logo]()
$267
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 October 28, 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 October 28, 2026.
This Delta deal was found by Cheapflights users on 10/27. 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 11/133:59 pm -
1 stop5h 56m
Thu 11/195:05 pm -
1 stop7h 05m
Deal found 10/27![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/910:40 pm -
Nonstop3h 45m
Mon 11/168:55 pm -
Nonstop4h 30m
Deal found 10/23![Southwest logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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 11/129:15 am -
1 stop12h 44m
Sun 11/157:57 pm -
Nonstop4h 46m
Deal found 10/24![Alaska Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Wed 11/112:08 pm -
Nonstop4h 14m
Thu 11/128:02 pm -
Nonstop4h 38m
Deal found 10/24![United Airlines logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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 12/76:15 am -
1 stop8h 16m
Thu 12/107:58 pm -
Nonstop4h 51m
Deal found 10/24![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/24. 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 11/184:05 pm -
Nonstop3h 55m
Thu 11/197:05 am -
1 stop6h 45m
Deal found 10/24![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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 11/136:22 pm -
1 stop9h 18m
Mon 11/167:20 am -
Nonstop4h 43m
Deal found 10/24![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/26. 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 11/125:20 pm -
1 stop5h 50m
Sun 11/159:20 pm -
Nonstop4h 30m
Deal found 10/26![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Fri 12/184:20 pm -
Nonstop4h 09m
Sun 1/38:13 pm -
Nonstop4h 42m
Deal found 10/25![United Airlines logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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 12/97:00 am -
Nonstop4h 15m
Mon 12/149:00 am -
1 stop10h 45m
Deal found 10/24![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/27. 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 1/116:15 am -
Nonstop4h 15m
Fri 1/152:15 pm -
Nonstop4h 20m
Deal found 10/27![Southwest logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 11/1112:41 pm -
Nonstop4h 18m
Sun 11/157:20 am -
Nonstop4h 43m
Deal found 10/27![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/26. 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 12/108:20 am -
2 stops7h 05m
Thu 12/175:55 am -
1 stop6h 05m
Deal found 10/26![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 10/23. 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.
Wed 12/168:15 am -
2 stops7h 05m
Fri 12/186:00 am -
2 stops7h 20m
Deal found 10/23![Southwest logo]()
$298
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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 11/97:45 pm -
1 stop7h 55m
Thu 11/127:20 am -
Nonstop4h 43m
Deal found 10/26![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 10/27. 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 11/118:20 am -
2 stops7h 05m
Sat 11/1412:55 pm -
1 stop6h 50m
Deal found 10/27![Southwest logo]()
$298
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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 11/65:35 pm -
Nonstop4h 14m
Mon 11/97:20 am -
Nonstop4h 43m
Deal found 10/26![Alaska Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 10/27. 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 11/178:20 am -
2 stops7h 25m
Thu 11/197:05 am -
1 stop6h 45m
Deal found 10/27![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/2310:40 pm -
Nonstop3h 45m
Fri 11/275:10 am -
1 stop6h 30m
Deal found 10/23![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 10/26. 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 11/75:00 pm -
Nonstop3h 55m
Wed 11/118:55 pm -
Nonstop4h 30m
Deal found 10/26![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 10/26. 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 12/151:25 pm -
1 stop7h 15m
Sat 12/199:35 pm -
Nonstop4h 20m
Deal found 10/26![Southwest logo]()
$337
Last-minute flights from San Diego to ChicagoDiscover last-minute flight deals from San Diego to Chicago. Data last updated October 28, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chicago. Data last updated October 28, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:25 am -
1 stop15h 56m
Tue 11/106:30 am -
1 stop19h 27m
Deal found 10/23![Frontier logo]()
$271
This Cheapflightsfares deal was found by Cheapflights users on 10/24. 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 11/46:25 am -
1 stop15h 56m
Tue 11/106:30 am -
1 stop19h 27m
Deal found 10/24![Frontier logo]()
$274
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:25 am -
1 stop15h 56m
Mon 11/96:30 am -
1 stop19h 27m
Deal found 10/23![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 10/27. 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.
Thu 11/59:32 am -
1 stop7h 43m
Sun 11/86:30 am -
1 stop11h 38m
Deal found 10/27![Frontier logo]()
$278
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/910:40 pm -
Nonstop3h 45m
Mon 11/168:55 pm -
Nonstop4h 30m
Deal found 10/23![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 10/25. 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 11/108:20 am -
2 stops7h 05m
Sun 11/159:20 pm -
Nonstop4h 30m
Deal found 10/25![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/26. 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 11/129:25 pm -
1 stop6h 15m
Sun 11/225:10 am -
1 stop6h 30m
Deal found 10/26![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 10/27. 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 11/1310:40 pm -
Nonstop3h 45m
Sun 11/229:20 pm -
Nonstop4h 30m
Deal found 10/27![Southwest logo]()
$277
This Mytrip deal was found by Cheapflights users on 10/26. 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 11/168:20 pm -
2 stops13h 02m
Wed 11/1812:27 pm -
2 stops23h 44m
Deal found 10/26![Frontier logo]()
$274
This Southwest deal was found by Cheapflights users on 10/24. 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 11/174:05 pm -
Nonstop3h 55m
Thu 11/197:05 am -
1 stop6h 45m
Deal found 10/24![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/27. 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 11/216:25 pm -
Nonstop3h 50m
Wed 11/256:00 am -
Nonstop4h 30m
Deal found 10/27![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 10/26. 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 11/216:25 pm -
Nonstop3h 50m
Tue 11/2410:00 am -
1 stop6h 25m
Deal found 10/26![Southwest logo]()
$276
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 October 28, 2026.
Search for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated October 28, 2026.
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Thu 11/196:25 am -
2 stops20h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:02 pm -
2 stops14h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/216:30 am -
2 stops23h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$133
This eDestinos deal was found by Cheapflights users on 10/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:06 am -
2 stops35h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$134
This American Airlines deal was found by Cheapflights users on 10/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:50 am -
Nonstop4h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:25 am -
1 stop8h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$135
This Mytrip deal was found by Cheapflights users on 10/27. 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 11/168:20 pm -
2 stops13h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$136
This eDestinos deal was found by Cheapflights users on 10/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:25 am -
2 stops24h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:32 am -
1 stop23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$137
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Sun 11/225:29 pm -
2 stops23h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$138
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 11/96:50 am -
Nonstop4h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![United Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 10/23. 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.
Fri 11/610:40 pm -
Nonstop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![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 October 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Kiwi.com) |
One-way from | $132 (Mytrip) |
Popular in | July |
Cheapest in | February |
Average price | $348 |
Good round-trip deal | $353 or less |
Good one-way deal | $205 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 October 28, 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 - ORD Chicago O'Hare Intl
SANORD
San Diego
Mon 11/30
5:32 pm-11:49 pm
Nonstop4h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$137
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Tue 12/1
7:00 am-1:15 pm
Nonstop4h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$137
San DiegoChicago
SAN San Diego - ORD Chicago O'Hare Intl
SANORD
San Diego
Tue 11/10
10:40 am-4:54 pm
Nonstop4h 14m
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 11/21
10:40 pm-4:25 am
Nonstop3h 45m
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
Thu 12/3
12:42 pm-7:00 pm
Nonstop4h 18m
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 11/21
5:32 pm-11:49 pm
Nonstop4h 17m
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
Wed 12/23
10:30 pm-9:49 am
1 stop9h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$147
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Thu 11/12
6:25 am-4:39 pm
1 stop8h 14m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$147
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 11/17
6:25 am-4:39 pm
1 stop8h 14m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$147
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 11/10
8:05 pm-5:45 am
1 stop7h 40m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
Showing 1-10 of 43 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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-ORD
SAN-MDW
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
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 $253). 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 October 28, 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.
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 $414 in November.The cheapest round-trip price found within the last 5 days was $259 on Frontier (Nov 13-Nov 14).
How often are flights from San Diego to Chicago delayed?
About 9% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 192 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 Friday 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 6% 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 October 24, 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 October 28, 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.
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
Boarding
8.1
Overall
7.9
Entertainment
7.0
Food
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
2.0
MediocreArt,Dec 2025
SAN - OGG
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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Other flights to Chicago
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San Diego and Chicago flights
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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 7,457,451 searches. Data last updated October 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$338 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$178 | Average$356 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$408 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$237 | Average$319 | FlexibilityNo cancel fee | On-time62% |