$216+ Cheap flights from San José (SJO) 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from San José 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 José Juan Santamaria Intl to Chicago are usually found in January or February, booked 90 days in advance, depart on a Tuesday or Friday and return on a Tuesday
Cheap flight deals from San José to Chicago
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Cheapest flights from San José to ChicagoExplore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Avianca deal was found by Cheapflights users on 10/28. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:30 am -
1 stop11h 00m
Mon 12/710:30 pm -
1 stop17h 50m
Deal found 10/28![Avianca logo]()
$403
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:50 am -
1 stop18h 40m
Mon 12/710:30 pm -
1 stop17h 50m
Deal found 10/27![Avianca logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 10/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:12 pm -
1 stop22h 34m
Mon 4/53:13 pm -
1 stop9h 45m
Deal found 10/29![Copa Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/231:25 pm -
Nonstop5h 32m
Thu 12/315:30 am -
1 stop15h 09m
Deal found 10/28![United Airlines logo]()
$408
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:37 pm -
1 stop8h 17m
Sat 11/286:00 am -
1 stop16h 15m
Deal found 10/26![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/191:55 pm -
1 stop10h 06m
Sun 11/2912:25 am -
1 stop11h 00m
Deal found 10/29![United Airlines logo]()
$409
This Avianca deal was found by Cheapflights users on 10/28. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:55 am -
1 stop18h 35m
Sat 12/122:20 pm -
1 stop8h 55m
Deal found 10/28![Avianca logo]()
$411
This Avianca deal was found by Cheapflights users on 10/28. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:30 am -
1 stop11h 00m
Sat 12/122:20 pm -
1 stop8h 55m
Deal found 10/28![Avianca logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/1111:28 pm -
1 stop11h 19m
Thu 2/117:02 am -
Nonstop5h 13m
Deal found 10/29![United Airlines logo]()
$413
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:35 am -
1 stop7h 20m
Thu 1/72:20 pm -
1 stop8h 55m
Deal found 10/25![Avianca logo]()
$414
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/196:22 am -
1 stop15h 08m
Sat 1/25:21 am -
1 stop7h 10m
Deal found 10/28![American Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/141:55 pm -
Nonstop5h 33m
Fri 11/276:30 pm -
1 stop18h 12m
Deal found 10/29![United Airlines logo]()
$421
Best flights from San José to ChicagoDiscover carefully curated flight deals from San José to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from San José to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:12 pm -
1 stop22h 34m
Mon 4/53:13 pm -
1 stop9h 45m
Deal found 10/29![Copa Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/191:55 pm -
1 stop10h 06m
Sun 11/2912:25 am -
1 stop11h 00m
Deal found 10/29![United Airlines logo]()
$409
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.
Wed 11/112:15 pm -
1 stop8h 55m
Sun 11/155:15 am -
1 stop7h 05m
Deal found 10/25![Southwest logo]()
$507
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am -
1 stop9h 18m
Sun 11/159:30 am -
2 stops12h 45m
Deal found 10/25![Delta logo]()
$557
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.
Wed 11/112:25 pm -
1 stop10h 20m
Sun 11/157:29 am -
1 stop13h 10m
Deal found 10/25![United Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 10/29. 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 1/131:25 pm -
Nonstop5h 32m
Wed 1/209:18 am -
1 stop11h 21m
Deal found 10/29![United Airlines logo]()
$474
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:55 pm -
1 stop18h 51m
Mon 11/237:35 am -
1 stop25h 32m
Deal found 10/25![Copa Airlines logo]()
$537
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am -
2 stops11h 30m
Sun 11/158:29 am -
2 stops13h 46m
Deal found 10/25![Delta logo]()
$557
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/251:15 am -
1 stop22h 09m
Thu 12/318:30 pm -
1 stop16h 12m
Deal found 10/27![United Airlines logo]()
$475
This Southwest deal was found by Cheapflights users on 10/29. 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 1/141:50 pm -
1 stop9h 00m
Fri 1/225:20 am -
1 stop8h 25m
Deal found 10/29![Southwest logo]()
$598
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:35 pm -
1 stop19h 16m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 10/26![United Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 10/29. 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 1/233:55 pm -
1 stop8h 00m
Sat 1/309:38 am -
2 stops12h 11m
Deal found 10/29![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 10/29. 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 1/142:23 pm -
1 stop7h 54m
Thu 1/219:38 am -
2 stops12h 11m
Deal found 10/29![Delta logo]()
$597
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/211:55 pm -
Nonstop5h 33m
Sat 11/286:59 am -
1 stop12h 54m
Deal found 10/29![United Airlines logo]()
$541
This Southwest deal was found by Cheapflights users on 10/29. 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 12/52:40 pm -
1 stop7h 40m
Sun 12/138:40 pm -
2 stops15h 40m
Deal found 10/29![Southwest logo]()
$741
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
2 stops11h 04m
Wed 11/251:05 pm -
1 stop9h 10m
Deal found 10/26![Delta logo]()
$664
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/221:25 pm -
Nonstop5h 32m
Thu 1/710:30 am -
1 stop10h 09m
Deal found 10/29![United Airlines logo]()
$560
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.
Sun 12/273:25 pm -
2 stops17h 15m
Wed 3/318:35 am -
2 stops12h 05m
Deal found 10/27![Southwest logo]()
$772
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/137:00 am -
1 stop15h 17m
Wed 1/209:38 am -
2 stops12h 11m
Deal found 10/29![Delta logo]()
$668
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/267:00 am -
1 stop15h 22m
Thu 12/319:58 am -
1 stop11h 48m
Deal found 10/26![Delta logo]()
$794
Last-minute flights from San José to ChicagoDiscover last-minute flight deals from San José to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:50 am -
1 stop18h 40m
Thu 11/510:30 pm -
1 stop17h 50m
Deal found 10/26![Avianca logo]()
$403
This FlightHub deal was found by Cheapflights users on 10/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:30 am -
1 stop11h 00m
Tue 11/1010:30 pm -
1 stop10h 20m
Deal found 10/29![Avianca logo]()
$429
This Avianca deal was found by Cheapflights users on 10/29. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:30 am -
1 stop11h 00m
Sat 12/122:20 pm -
1 stop8h 55m
Deal found 10/29![Avianca logo]()
$411
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:30 am -
1 stop11h 00m
Sat 11/1410:30 pm -
1 stop10h 20m
Deal found 10/27![Avianca logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/141:55 pm -
Nonstop5h 33m
Fri 11/276:30 pm -
1 stop18h 12m
Deal found 10/29![United Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/141:55 pm -
Nonstop5h 33m
Thu 11/266:55 am -
1 stop13h 44m
Deal found 10/29![United Airlines logo]()
$426
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
2 stops26h 46m
Sat 11/286:00 am -
1 stop16h 15m
Deal found 10/26![Delta logo]()
$422
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
2 stops24h 49m
Sat 11/286:49 am -
1 stop15h 26m
Deal found 10/26![Delta logo]()
$422
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:37 pm -
1 stop8h 17m
Sat 11/286:00 am -
1 stop16h 15m
Deal found 10/26![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/192:25 pm -
1 stop17h 26m
Sat 11/2812:01 am -
1 stop20h 38m
Deal found 10/29![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 11/213:03 pm -
1 stop9h 17m
Sat 11/285:00 am -
1 stop17h 47m
Deal found 10/29![American Airlines logo]()
$418
This Avianca deal was found by Cheapflights users on 10/28. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:50 am -
1 stop18h 40m
Mon 1/42:20 pm -
1 stop18h 15m
Deal found 10/28![Avianca logo]()
$406
One-way flights from San José to ChicagoSearch for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Volaris deal was found by Cheapflights users on 10/29. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$216
This Viva deal was found by Cheapflights users on 10/29. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:30 am -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Viva logo]()
$222
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 3/43:00 pm -
1 stop20h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$229
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$235
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 12/86:53 am -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 10/28. 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 2/112:45 pm -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$249
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.
Mon 12/76:53 am -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$249
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/133:00 pm -
1 stop20h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$253
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/204:12 pm -
1 stop18h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 10/28. 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 2/52:45 pm -
2 stops16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$259
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.
Wed 11/41:20 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$267
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.
Sun 12/66:53 am -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$267
Find flight deals from San José to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) 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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $383 (Volaris) |
One-way from | $216 (Volaris) |
Popular in | July |
Cheapest in | January |
Average price | $509 |
Good round-trip deal | $408 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San José 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 30, 2026.
Use the filters below to find and compare flights from San José to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 11/5
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$216
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 12/10
2:30 am-11:00 pm
1 stop20h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 11/15
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 2/11
3:00 pm-11:13 am
1 stop20h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 2/13
3:00 pm-11:13 am
1 stop20h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$253
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 2/11
1:05 pm-11:55 pm
2 stops10h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 3/27
3:00 pm-11:59 am
1 stop19h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$290
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Tue 4/20
9:00 am-11:10 pm
1 stop13h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$292
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 2/13
2:45 pm-10:45 pm
1 stop8h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$299
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Fri 11/6
1:20 pm-12:10 am
2 stops10h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$314
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from San José 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 José to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San José-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-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 José-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 José to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San José with our price prediction graph.
SJO-CHI
SJO-ORD
SJO-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 José to Chicago
SJO-CHI
SJO-ORD
SJO-MDW
What is the cheapest month to book a flight from San José to Chicago?
Currently, January is the cheapest month in which you can book a flight from San José to Chicago (average of $396). Flying from San José to Chicago in July is currently the most expensive (average of $639). 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.
How much does it cost to fly round-trip from San José to Chicago?
Airfare is typical for this route at the moment.
San José to Chicago flights typically cost between $382 and $506 in April.The cheapest round-trip price found within the last 5 days was $383 on Multiple Airlines (Apr 8-Apr 13).
How often are flights from San José to Chicago delayed?
About 5% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 239 minutes.
What is the most punctual flight time for San José to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon 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 José to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.
How far ahead should I book a flight from San José to Chicago?
To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 89 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 30, 2026.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.4
Overall
7.9
Boarding
8.1
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 José to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Chicago
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San José and Chicago flights
Browse other San José and Chicago flight options. Last updated on October 30, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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Top 5 airlines flying from San José to Chicago
Discover the top 5 airlines that operate flights from San José 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$488 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$351 | Average$521 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$492 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$382 | Average$474 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$390 | Average$693 | FlexibilityNo cancel fee | On-time63% |