$183+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jul 19 — Jul 261
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 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
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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 June 19, 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 June 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Tue 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/14![JetBlue logo]()
$385
This Southwest deal was found by Cheapflights users on 6/15. 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 9/161:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Tue 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 6/15![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Thu 10/15:05 am
MDW
- SJO
1 stop7h 55m
Southwest
Deal found 6/14![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:00 am
SJO
- MDW
1 stop11h 30m
Southwest
Mon 9/75:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 6/16![Southwest logo]()
$414
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:00 am
SJO
- MDW
1 stop11h 30m
Southwest
Thu 9/2410:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Deal found 6/16![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:00 am
SJO
- MDW
2 stops11h 55m
Southwest
Tue 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 6/17![Southwest logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Tue 10/139:33 pm
ORD
- SJO
2 stops18h 38m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$420
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Mon 9/282:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$429
This Volaris deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 10/154:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 10/201:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:00 am
SJO
- MDW
2 stops9h 20m
Southwest
Tue 11/105:15 am
MDW
- SJO
1 stop8h 00m
Southwest
Deal found 6/18![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Mon 9/215:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 6/16![Southwest logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Wed 10/147:00 am
ORD
- SJO
2 stops33h 11m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$442
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 June 19, 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 June 19, 2026.
This Copa Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 8/74:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Mon 8/173:21 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:25 pm
SJO
- ORD
1 stop18h 44m
United Airlines
Mon 9/147:52 pm
ORD
- SJO
1 stop17h 29m
United Airlines
Deal found 6/17![United Airlines logo]()
$508
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/21:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sun 9/66:55 am
MDW
- SJO
1 stop12h 45m
Southwest
Deal found 6/18![Southwest logo]()
$549
This Delta deal was found by Cheapflights users on 6/14. 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.
Wed 9/161:25 pm
SJO
- MDW
1 stop8h 00m
Delta
Sat 9/196:05 am
MDW
- SJO
1 stop6h 49m
Delta
Deal found 6/14![Delta logo]()
$667
This Copa Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/174:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Fri 9/253:20 pm
ORD
- SJO
1 stop20h 38m
Copa Airlines
Deal found 6/18![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/2510:03 am
SJO
- ORD
1 stop26h 56m
Copa Airlines
Sat 8/298:02 am
ORD
- SJO
1 stop25h 17m
Copa Airlines
Deal found 6/19![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/1210:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Sat 8/223:21 pm
ORD
- SJO
1 stop18h 43m
Copa Airlines
Deal found 6/18![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:45 am
SJO
- MDW
1 stop8h 15m
Southwest
Thu 7/3010:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Deal found 6/14![Southwest logo]()
$607
This Copa Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/214:08 am
SJO
- ORD
1 stop8h 49m
Copa Airlines
Sun 7/263:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:00 am
SJO
- MDW
2 stops10h 40m
Southwest
Mon 9/217:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 6/16![Southwest logo]()
$612
This Copa Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/114:08 am
SJO
- ORD
1 stop8h 51m
Copa Airlines
Tue 8/258:02 am
ORD
- SJO
1 stop25h 17m
Copa Airlines
Deal found 6/19![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/17. 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.
Sat 7/255:45 am
SJO
- ORD
1 stop17h 16m
Copa Airlines
Tue 7/288:02 am
ORD
- SJO
1 stop25h 19m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 6/15. 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 8/51:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Sat 8/86:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 6/15![Delta logo]()
$818
This Copa Airlines deal was found by Cheapflights users on 6/16. 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 8/225:45 am
SJO
- ORD
1 stop18h 17m
Copa Airlines
Sun 8/308:02 am
ORD
- SJO
1 stop24h 08m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/15. 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 7/181:10 pm
SJO
- MDW
1 stop9h 35m
Southwest
Fri 7/2411:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$750
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Sat 6/2710:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Deal found 6/18![Southwest logo]()
$757
This Southwest deal was found by Cheapflights users on 6/15. 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 7/308:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Fri 12/115:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Deal found 6/15![Southwest logo]()
$807
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/91:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Mon 7/137:50 am
MDW
- SJO
2 stops12h 50m
Southwest
Deal found 6/18![Southwest logo]()
$807
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:40 pm
SJO
- MDW
1 stop8h 20m
Southwest
Tue 6/305:10 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 6/17![Southwest logo]()
$835
Last-minute flights from San José to ChicagoDiscover last-minute flight deals from San José to Chicago. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Chicago. Data last updated June 19, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 6/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/223:10 pm
SJO
- ORD
1 stop23h 45m
Avianca
Thu 6/258:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/15![Avianca logo]()
$477
This eDestinos deal was found by Cheapflights users on 6/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:05 am
SJO
- ORD
1 stop9h 50m
Avianca
Thu 6/258:40 am
ORD
- SJO
1 stop24h 50m
Avianca
Deal found 6/16![Avianca logo]()
$472
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:40 am
SJO
- ORD
1 stop29h 15m
Avianca
Sat 6/278:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/17![Avianca logo]()
$482
This FlightHub deal was found by Cheapflights users on 6/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:05 am
SJO
- ORD
1 stop9h 50m
Avianca
Sat 6/278:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/15![Avianca logo]()
$460
This Expedia deal was found by Cheapflights users on 6/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:45 am
SJO
- ORD
1 stop12h 25m
Frontier
Sat 7/255:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 6/17![Frontier logo]()
$475
This Expedia deal was found by Cheapflights users on 6/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/199:35 am
SJO
- ORD
1 stop22h 36m
Frontier
Fri 7/245:13 pm
ORD
- SJO
1 stop16h 17m
Frontier
Deal found 6/14![Frontier logo]()
$496
This Avianca deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/217:45 pm
SJO
- ORD
2 stops10h 42m
Avianca
Sat 7/255:15 pm
ORD
- SJO
1 stop7h 25m
Avianca
Deal found 6/19![Avianca logo]()
$459
This Copa Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 7/214:08 am
SJO
- ORD
1 stop8h 49m
Copa Airlines
Sun 7/263:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/221:40 pm
SJO
- MDW
1 stop9h 15m
Southwest
Tue 7/288:40 am
MDW
- SJO
2 stops12h 00m
Southwest
Deal found 6/18![Southwest logo]()
$591
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/238:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Wed 7/2912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
Deal found 6/18![Southwest logo]()
$544
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:30 am
SJO
- ORD
1 stop23h 15m
United Airlines
Wed 8/58:02 pm
ORD
- SJO
1 stop15h 09m
United Airlines
Deal found 6/14![United Airlines logo]()
$497
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/309:35 am
SJO
- MDW
2 stops11h 28m
Frontier
Wed 8/54:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Deal found 6/18![Frontier logo]()
$600
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 June 19, 2026.
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/132:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/17![JetBlue logo]()
$183
This Air Canada deal was found by Cheapflights users on 6/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/297:15 am
SJO
- ORD
2 stops29h 04m
Air Canada
Deal found 6/16![Air Canada logo]()
$246
This Mytrip deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/227:15 am
SJO
- ORD
2 stops31h 35m
Air Canada
Deal found 6/19![Air Canada logo]()
$255
This Volaris deal was found by Cheapflights users on 6/14. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$263
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/15![Frontier logo]()
$267
This SmartFares deal was found by Cheapflights users on 6/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/15![JetBlue logo]()
$271
This Priceline deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Sun 8/29:35 am
SJO
- ORD
1 stop22h 36m
Frontier
Deal found 6/19![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 10/78:55 am
SJO
- MDW
2 stops25h 03m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$279
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:15 am
SJO
- ORD
2 stops25h 30m
Air Canada
Deal found 6/16![Air Canada logo]()
$279
This Southwest deal was found by Cheapflights users on 6/15. 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 10/159:00 am
SJO
- MDW
1 stop9h 05m
Southwest
Deal found 6/15![Southwest logo]()
$281
This JetBlue deal was found by Cheapflights users on 6/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/15![JetBlue logo]()
$281
This Mytrip deal was found by Cheapflights users on 6/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$283
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 June 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $385 (Cheapflightsfares) |
One-way from | $183 (JetBlue) |
Popular in | June |
Cheapest in | January |
Average price | $535 |
Good one-way deal | $353 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 June 19, 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
Fri 8/7
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Mon 8/17
3:21 pm-8:19 am
1 stop17h 58m
$459
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 8/17
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Fri 9/25
3:20 pm-10:58 am
1 stop20h 38m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/25
10:03 am-1:59 pm
1 stop26h 56m
Chicago O'Hare Intl
Sat 8/29
8:02 am-8:19 am
1 stop25h 17m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 8/12
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sat 8/22
3:21 pm-9:04 am
1 stop18h 43m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 7/21
4:08 am-1:57 pm
1 stop8h 49m
Chicago O'Hare Intl
Sun 7/26
3:21 pm-7:26 am
1 stop17h 05m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/11
4:08 am-1:59 pm
1 stop8h 51m
Chicago O'Hare Intl
Tue 8/25
8:02 am-8:19 am
1 stop25h 17m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 7/25
5:45 am-12:01 am
1 stop17h 16m
Chicago O'Hare Intl
Tue 7/28
8:02 am-8:21 am
1 stop25h 19m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/22
5:45 am-1:02 am
1 stop18h 17m
Chicago O'Hare Intl
Sun 8/30
8:02 am-7:10 am
1 stop24h 08m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 9/4
1:25 pm-9:09 am
1 stop18h 44m
Chicago O'Hare Intl
Mon 9/14
7:52 pm-12:21 pm
1 stop17h 29m
$508
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 9/2
1:40 pm-11:10 pm
1 stop8h 30m
Chicago Midway
Sun 9/6
6:55 am-6:40 pm
1 stop12h 45m
$549
Showing 1-10 of 39 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 June.
| 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, April is the cheapest month in which you can book a flight from San José to Chicago (average of $103). 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 June 19, 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 238 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.
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 29 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 June 19, 2026.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest,Delta, andCopa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Crew
8.6
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
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Alternative routes for San José to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 19, 2026.
Complete your trip
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Search flights from San José to Chicago by cabin class
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San José and Chicago flights
Browse other San José and Chicago flight options. Last updated on June 19, 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 June 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$488 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$512 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$367 | Average$632 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |