$166+ Cheap flights from Chicago (CHI) to San José (SJO)
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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San José with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in February or January, booked 9 days in advance, depart on a Tuesday or Monday and return on a Tuesday
Cheap flight deals from Chicago to San José
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Cheapest flights from Chicago to San JoséExplore the most affordable flight options available from Chicago to San José. 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 Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:13 pm -
1 stop18h 06m
Fri 11/2010:03 am -
1 stop14h 08m
Deal found 10/26![Copa Airlines logo]()
$427
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 11/286:05 am -
1 stop16h 42m
Sat 12/123:54 pm -
1 stop15h 44m
Deal found 10/28![American Airlines logo]()
$439
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:50 pm -
2 stops20h 17m
Thu 12/36:07 am -
2 stops11h 17m
Deal found 10/26![American Airlines logo]()
$443
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/69:06 pm -
1 stop15h 31m
Sat 12/1912:43 am -
1 stop11h 52m
Deal found 10/25![American Airlines logo]()
$444
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.
Fri 12/47:50 pm -
1 stop19h 02m
Tue 12/82:46 pm -
1 stop9h 13m
Deal found 10/27![American Airlines logo]()
$450
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.
Sat 11/147:17 am -
Nonstop5h 18m
Sat 11/212:15 pm -
1 stop9h 46m
Deal found 10/27![United Airlines logo]()
$451
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:20 pm -
1 stop23h 35m
Sat 1/164:15 pm -
1 stop20h 40m
Deal found 10/26![Avianca logo]()
$452
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:50 pm -
1 stop19h 02m
Sat 12/1912:43 am -
1 stop11h 52m
Deal found 10/26![American Airlines logo]()
$455
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.
Sat 11/75:30 am -
1 stop7h 52m
Sat 11/2111:28 pm -
1 stop10h 17m
Deal found 10/27![United Airlines logo]()
$456
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 11/148:30 am -
2 stops12h 20m
Fri 11/203:03 pm -
1 stop9h 17m
Deal found 10/28![American Airlines logo]()
$460
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:13 pm -
1 stop20h 46m
Sun 11/85:37 am -
1 stop18h 34m
Deal found 10/27![Copa Airlines logo]()
$461
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:20 pm -
1 stop23h 35m
Sun 1/174:15 pm -
1 stop20h 40m
Deal found 10/27![Avianca logo]()
$462
Best flights from Chicago to San JoséDiscover carefully curated flight deals from Chicago to San José 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 Chicago to San José 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.
Fri 2/122:13 pm -
1 stop16h 51m
Fri 2/199:57 am -
1 stop14h 14m
Deal found 10/29![Copa 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.
Mon 2/157:02 am -
Nonstop5h 13m
Fri 2/2612:35 pm -
1 stop8h 54m
Deal found 10/29![United Airlines logo]()
$434
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:53 pm -
1 stop11h 06m
Sun 11/154:15 pm -
1 stop18h 58m
Deal found 10/28![Multiple Airlines logo]()
$482
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 2/37:00 am -
2 stops14h 49m
Mon 2/87:00 am -
1 stop8h 53m
Deal found 10/25![Delta logo]()
$490
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.
Fri 2/55:20 am -
1 stop8h 25m
Tue 2/91:50 pm -
1 stop9h 00m
Deal found 10/25![Southwest logo]()
$552
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 2/57:02 am -
Nonstop5h 13m
Mon 2/81:15 am -
1 stop8h 55m
Deal found 10/25![United Airlines logo]()
$434
This Delta 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 Delta is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Fri 11/2711:27 am -
1 stop10h 48m
Fri 12/42:37 pm -
1 stop8h 17m
Deal found 10/28![Delta logo]()
$533
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 1/189:18 am -
1 stop11h 21m
Fri 1/221:25 pm -
Nonstop5h 32m
Deal found 10/26![United Airlines logo]()
$579
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.
Mon 11/237:05 am -
2 stops15h 10m
Thu 11/262:37 pm -
1 stop8h 43m
Deal found 10/26![Delta logo]()
$584
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.
Fri 2/129:35 pm -
1 stop15h 15m
Fri 2/192:45 pm -
2 stops18h 05m
Deal found 10/29![Southwest logo]()
$686
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.
Fri 3/512:30 pm -
1 stop8h 09m
Sat 3/1312:15 am -
1 stop8h 10m
Deal found 10/26![United Airlines logo]()
$586
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 2/127:02 am -
Nonstop5h 13m
Thu 2/181:25 pm -
Nonstop5h 32m
Deal found 10/27![United Airlines logo]()
$591
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.
Fri 1/296:00 am -
1 stop6h 58m
Sat 2/63:55 pm -
1 stop8h 00m
Deal found 10/26![Delta logo]()
$660
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.
Sun 2/75:20 am -
1 stop8h 25m
Sun 2/212:45 pm -
2 stops9h 35m
Deal found 10/29![Southwest logo]()
$743
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.
Sun 2/77:02 am -
Nonstop5h 13m
Sun 2/212:15 pm -
1 stop9h 10m
Deal found 10/29![United Airlines logo]()
$594
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 1/169:38 am -
2 stops12h 11m
Sat 1/303:55 pm -
1 stop8h 00m
Deal found 10/26![Delta logo]()
$664
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 12/65:10 am -
1 stop8h 05m
Mon 12/72:15 pm -
1 stop8h 55m
Deal found 10/27![Southwest logo]()
$753
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.
Mon 11/99:30 am -
2 stops12h 45m
Fri 11/137:00 am -
2 stops11h 04m
Deal found 10/26![Delta logo]()
$681
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 11/134:39 pm -
1 stop13h 46m
Wed 11/181:55 pm -
1 stop10h 06m
Deal found 10/29![United Airlines logo]()
$623
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 2/137:15 am -
1 stop7h 45m
Mon 2/221:05 pm -
2 stops11h 15m
Deal found 10/29![Southwest logo]()
$758
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.
Thu 12/36:00 am -
1 stop7h 12m
Sun 12/67:00 am -
1 stop9h 16m
Deal found 10/27![Delta logo]()
$810
Last-minute flights from Chicago to San JoséDiscover last-minute flight deals from Chicago to San José. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José. Data last updated October 30, 2026 and is based on user searches.
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:13 pm -
1 stop20h 46m
Sun 11/85:37 am -
1 stop18h 34m
Deal found 10/27![Copa Airlines logo]()
$461
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.
Tue 11/37:29 am -
1 stop13h 10m
Sat 11/71:55 pm -
Nonstop5h 33m
Deal found 10/26![United Airlines logo]()
$463
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.
Sat 11/75:30 am -
1 stop7h 52m
Sat 11/2111:28 pm -
1 stop10h 17m
Deal found 10/27![United Airlines logo]()
$456
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:50 pm -
1 stop18h 59m
Wed 11/183:54 pm -
1 stop8h 54m
Deal found 10/25![American Airlines logo]()
$467
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.
Sat 11/147:17 am -
Nonstop5h 18m
Sat 11/212:15 pm -
1 stop9h 46m
Deal found 10/27![United Airlines logo]()
$451
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 11/148:30 am -
2 stops12h 20m
Sat 11/213:52 pm -
1 stop8h 56m
Deal found 10/28![American Airlines logo]()
$460
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 11/149:30 am -
2 stops12h 45m
Wed 11/182:37 pm -
2 stops19h 09m
Deal found 10/29![Delta logo]()
$464
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 11/1411:18 am -
2 stops10h 57m
Wed 11/182:37 pm -
1 stop18h 04m
Deal found 10/29![Delta logo]()
$464
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.
Sat 11/147:17 am -
Nonstop5h 18m
Mon 11/162:25 pm -
1 stop10h 20m
Deal found 10/27![United Airlines logo]()
$468
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:13 pm -
1 stop18h 06m
Fri 11/2010:03 am -
1 stop14h 08m
Deal found 10/26![Copa Airlines logo]()
$427
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:50 pm -
2 stops20h 17m
Thu 12/36:07 am -
1 stop12h 18m
Deal found 10/26![American Airlines logo]()
$443
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 11/286:05 am -
1 stop16h 42m
Sat 12/123:54 pm -
1 stop15h 44m
Deal found 10/28![American Airlines logo]()
$439
One-way flights from Chicago to San JoséSearch for one-way flight options from Chicago to San José. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Chicago to San José. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/612:53 pm -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$166
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/11:48 pm -
1 stop11h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$168
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/41:48 pm -
1 stop11h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$173
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/201:29 pm -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$225
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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.
Thu 2/2512:53 pm -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$231
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/313:57 pm -
1 stop19h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$243
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:11 pm -
1 stop25h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$257
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 2/207:15 am -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$265
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.
Sun 1/245:20 am -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$275
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 2/258:50 pm -
2 stops16h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$280
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.
Wed 12/912:28 pm -
3 stops36h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$295
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.
Sun 12/68:40 pm -
2 stops15h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$300
Find flight deals from Chicago to San José
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San José (SJO). 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 | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $407 (Volaris) |
One-way from | $166 (FlightHub) |
Popular in | December |
Cheapest in | February |
Average price | $532 |
Good round-trip deal | $509 or less |
Good one-way deal | $410 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San José 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 Chicago to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Thu 2/25
12:53 pm-10:44 pm
1 stop9h 51m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 3/9
5:20 am-1:45 pm
1 stop8h 25m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$313
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 4/5
5:05 am-12:55 pm
1 stop8h 50m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$323
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 4/4
8:00 am-7:40 pm
2 stops12h 40m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$339
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sat 11/28
6:35 am-1:45 pm
1 stop7h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$343
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Mon 2/1
7:00 am-2:00 pm
1 stop7h 00m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$348
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Thu 12/31
7:00 am-2:01 pm
1 stop7h 01m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$362
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Fri 12/11
5:15 am-12:20 pm
1 stop7h 05m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$390
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Sat 11/28
7:17 am-12:35 pm
Nonstop5h 18m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$420
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 12/9
11:28 am-10:17 pm
1 stop10h 49m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$425
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Chicago to San José
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San José in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-San José flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-San José flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San José flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San José flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to San José
Have a flexible travel schedule? Discover the best time to fly to San José from Chicago with our price prediction graph.
CHI-SJO
ORD-SJO
MDW-SJO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to San José
CHI-SJO
ORD-SJO
MDW-SJO
What is the cheapest month to book a flight from Chicago to San José?
Currently, February is the cheapest month in which you can book a flight from Chicago to San José (average of $492). Flying from Chicago to San José in December is currently the most expensive (average of $691). 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 Chicago to San José?
Airfare is below average for this route at the moment.
Chicago to San José flights typically cost between $467 and $690 in February.The cheapest round-trip price found within the last 5 days was $407 on Multiple Airlines (Feb 13-Feb 20).
What’s the top layover airport for flights from Chicago to San José?
Share of 1-stop round-trip flights from Chicago to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.
Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San José on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to San José?
Average round-trip fare for 1-stop flights from Chicago to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $405.
What’s the fastest layover option from Chicago to San José?
Shortest average travel time for 1-stop one-way flights from Chicago to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Panama City (PTY) have the shortest average one-way travel time for 1-stop routes: 7h 49m.
Which airport typically offers the quickest layover for flights from Chicago to San José?
Average layover duration for 1-stop one-way flights from Chicago to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 29m.
How often are flights from Chicago to San José delayed?
About 20% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 151 minutes.
What is the most punctual flight time for Chicago to San José 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?
Saturday 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 Chicago to San José flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.
How far ahead should I book a flight from Chicago to San José?
The price you pay for your flight from Chicago to San José may vary depending on when you book. For the best chance of a lower fare, look to book 44 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José. Reviews last updated October 30, 2026.
Read through reviews of airlines operating flights from Chicago to San José, such as Southwest,Copa Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.4
Overall
7.9
Comfort
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Chicago to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Jacó
Heredia
Dominical
Manuel Antonio
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Top 9 airlines flying from Chicago to San José
Discover the top 9 airlines that operate flights from Chicago to San José. 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$149 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$303 | Average$544 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$324 | Average$642 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$352 | Average$551 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$364 | Average$492 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$384 | Average$740 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$390 | Average$608 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$606 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$395 | Average$649 | FlexibilityNo cancel fee | On-time63% |