$154+ Cheap flights from San José (SJO) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
May 18 — May 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 October, booked 30 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from San José to Chicago
Cheapest
Best
Last-minute
One-way
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 April 18, 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 April 18, 2026.
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/119:20 am
ORD
- SJO
3 stops27h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$348
This Volaris deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Mon 5/182:35 am
ORD
- SJO
1 stop22h 24m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$349
This Justfly.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:38 pm
SJO
- ORD
2 stops9h 29m
Spirit Airlines
Wed 4/297:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Thu 5/145:30 pm
ORD
- SJO
2 stops19h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sat 5/301:18 pm
ORD
- SJO
1 stop23h 27m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$358
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:35 am
SJO
- ORD
2 stops21h 20m
Frontier
Sat 6/65:11 pm
ORD
- SJO
1 stop16h 08m
Frontier
Deal found 4/14![Frontier logo]()
$360
This Justfly.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Fri 5/155:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SJO
1 stop7h 40m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/185:30 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:00 am
SJO
- MDW
1 stop8h 13m
Multiple Airlines
Sat 5/1611:59 am
MDW
- SJO
2 stops24h 46m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$432
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 April 18, 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 April 18, 2026.
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Sun 5/105:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$384
This Viva deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:20 am
SJO
- ORD
1 stop21h 20m
Viva
Fri 7/171:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 4/12![Viva logo]()
$458
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/301:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Sun 6/146:30 am
ORD
- SJO
1 stop17h 09m
United Airlines
Deal found 4/15![United Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 6/1410:05 am
SJO
- ORD
1 stop16h 55m
Copa Airlines
Mon 6/223:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/271:20 pm
SJO
- MDW
2 stops18h 23m
Delta
Tue 6/96:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 4/15![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 6/39:00 am
SJO
- MDW
1 stop7h 30m
Southwest
Wed 6/1012:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
Deal found 4/15![Southwest logo]()
$538
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/301:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Tue 6/99:21 pm
ORD
- SJO
1 stop13h 50m
United Airlines
Deal found 4/15![United Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:57 pm
SJO
- ORD
1 stop19h 09m
Copa Airlines
Thu 6/113:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/281:20 pm
SJO
- MDW
2 stops18h 23m
Delta
Sat 6/136:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 4/15![Delta logo]()
$476
This Copa Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:55 pm
SJO
- ORD
1 stop19h 02m
Copa Airlines
Sun 7/193:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/289:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Thu 6/1111:00 am
MDW
- SJO
2 stops9h 40m
Southwest
Deal found 4/15![Southwest logo]()
$542
This Copa Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Thu 5/214:10 am
SJO
- ORD
1 stop8h 56m
Copa Airlines
Mon 6/18:02 am
ORD
- SJO
1 stop11h 59m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Mon 5/1812:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Deal found 4/12![Southwest logo]()
$564
This Copa Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1410:05 am
SJO
- ORD
1 stop16h 55m
Copa Airlines
Thu 6/183:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Copa Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sat 5/166:19 pm
SJO
- ORD
1 stop18h 47m
Copa Airlines
Sat 5/303:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Sun 6/75:05 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 4/13![Southwest logo]()
$615
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Sat 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Deal found 4/14![Delta logo]()
$683
This Copa Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 6/128:47 am
SJO
- ORD
1 stop18h 13m
Copa Airlines
Sun 6/213:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Sun 6/287:25 am
MDW
- SJO
2 stops12h 15m
Southwest
Deal found 4/13![Southwest logo]()
$624
This Copa Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:47 am
SJO
- ORD
1 stop18h 13m
Copa Airlines
Wed 6/173:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Deal found 4/14![Copa Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:14 pm
SJO
- MDW
1 stop8h 03m
Delta
Thu 6/186:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 4/14![Delta logo]()
$711
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Sat 6/278:30 pm
MDW
- SJO
2 stops23h 10m
Southwest
Deal found 4/13![Southwest logo]()
$664
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:45 am
SJO
- MDW
2 stops12h 10m
Southwest
Fri 6/1211:35 am
MDW
- SJO
1 stop9h 05m
Southwest
Deal found 4/12![Southwest logo]()
$675
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/309:00 am
SJO
- MDW
1 stop10h 25m
Southwest
Tue 6/29:50 am
MDW
- SJO
2 stops10h 10m
Southwest
Deal found 4/15![Southwest logo]()
$738
Last-minute flights from San José to ChicagoDiscover last-minute flight deals from San José to Chicago. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Chicago. Data last updated April 18, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:38 pm
SJO
- ORD
2 stops9h 29m
Spirit Airlines
Wed 4/297:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:00 am
SJO
- MDW
1 stop8h 13m
Multiple Airlines
Sat 5/1611:59 am
MDW
- SJO
2 stops24h 46m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/119:20 am
ORD
- SJO
3 stops27h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Thu 5/145:30 pm
ORD
- SJO
2 stops19h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$357
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$340
This Justfly.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Fri 5/155:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$361
This Volaris deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Mon 5/182:35 am
ORD
- SJO
1 stop22h 24m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/185:30 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sat 5/301:18 pm
ORD
- SJO
1 stop23h 27m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SJO
1 stop7h 40m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$365
This Frontier deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:35 am
SJO
- MDW
2 stops11h 27m
Frontier
Wed 6/33:07 pm
MDW
- SJO
2 stops18h 12m
Frontier
Deal found 4/13![Frontier logo]()
$453
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 April 18, 2026.
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$154
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$160
This WAYA deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/101:00 pm
SJO
- ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/151:00 pm
SJO
- MDW
2 stops32h 02m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$196
This CheapOair deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/71:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$196
This Volaris deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- MDW
2 stops48h 12m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/17:45 pm
SJO
- MDW
2 stops16h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/197:00 am
SJO
- MDW
2 stops14h 02m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/171:00 pm
SJO
- MDW
2 stops21h 09m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$260
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 April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (CheapOair) |
One-way from | $154 (Trip.com) |
Popular in | March |
Cheapest in | January |
Average price | $460 |
Good round-trip deal | $470 or less |
Good one-way deal | $336 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 2,558,603 searches. Data last updated April 18, 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 - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/7
1:00 pm-9:54 am
2 stops19h 54m
Chicago O'Hare Intl
Sun 5/10
5:05 am-11:45 am
1 stop7h 40m
$384
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 7/10
2:20 am-12:40 am
1 stop21h 20m
Chicago O'Hare Intl
Fri 7/17
1:30 am-1:15 am
1 stop24h 45m
$458
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Sun 6/14
6:30 am-10:39 pm
1 stop17h 09m
$470
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Tue 6/9
9:21 pm-10:11 am
1 stop13h 50m
$470
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Mon 6/22
3:21 pm-9:06 am
1 stop18h 45m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 6/3
5:57 pm-2:06 pm
1 stop19h 09m
Chicago O'Hare Intl
Thu 6/11
3:21 pm-7:12 am
1 stop16h 51m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 7/13
5:55 pm-1:57 pm
1 stop19h 02m
Chicago O'Hare Intl
Sun 7/19
3:21 pm-7:26 am
1 stop17h 05m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/21
4:10 am-2:06 pm
1 stop8h 56m
Chicago O'Hare Intl
Mon 6/1
8:02 am-7:01 pm
1 stop11h 59m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Thu 6/18
3:21 pm-9:06 am
1 stop18h 45m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/16
6:19 pm-2:06 pm
1 stop18h 47m
Chicago O'Hare Intl
Sat 5/30
3:21 pm-9:06 am
1 stop18h 45m
$473
Showing 1-10 of 46 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| 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
How far ahead should I book a flight from San José to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San José to Chicago. Price data was last updated on April 10, 2026.
To ensure you get the cheapest price possible for a flight from San José to Chicago, you should look to book at least 30 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.
What is the cheapest month to book a flight from San José to Chicago?
Currently, November is the cheapest month in which you can book a flight from San José to Chicago (average of $111). Flying from San José to Chicago in December is currently the most expensive (average of $194). 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 SJO to CHI?
Find hourly flight availability from San José 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 April 18, 2026.
When flying from San José to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from San José to Chicago?
How often are flights from San José to Chicago delayed?
About 8% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 236 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 6% of flights being delayed.
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 April 18, 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.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from San José
Popular flights
Alternative routes for San José to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 18, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San José to Chicago by cabin class
Find flights from San José to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San José and Chicago flights
Browse other San José and Chicago flight options. Last updated on April 18, 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 April 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San José to Chicago
Discover the top 6 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 2,558,603 searches. Data last updated April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$300 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$189 | Average$448 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$249 | Average$421 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$332 | Average$491 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$387 | Average$476 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |