$165+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Mar 31 — Apr 71
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 Thursday or Tuesday 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 March 1, 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 March 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Mon 4/275:34 pm
ORD
- SJO
1 stop18h 41m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1412:19 pm
SJO
- ORD
2 stops25h 58m
Multiple Airlines
Mon 4/201:27 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$301
This Cheapflightsfares deal was found by Cheapflights users on 2/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Sun 5/105:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Thu 4/1612:20 pm
SJO
- ORD
1 stop10h 54m
Multiple Airlines
Tue 4/211:27 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Wed 5/135:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$309
This Cheapflightsfares deal was found by Cheapflights users on 2/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Tue 4/215:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$310
This eDestinos deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:18 pm
SJO
- ORD
1 stop18h 51m
Volaris
Thu 9/31:49 pm
ORD
- SJO
1 stop11h 10m
Volaris
Deal found 2/25![Volaris logo]()
$311
This Cheapflightsfares deal was found by Cheapflights users on 2/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Mon 4/205:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$312
This FlightHub deal was found by Cheapflights users on 2/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Tue 4/215:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Wed 4/295:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 4/1512:20 pm
SJO
- ORD
1 stop10h 54m
Multiple Airlines
Sun 4/195:25 am
ORD
- SJO
2 stops30h 50m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Wed 4/2912:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 2/27![Southwest logo]()
$392
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 March 1, 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 March 1, 2026.
This Copa Airlines deal was found by Cheapflights users on 2/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:19 pm
SJO
- ORD
1 stop18h 47m
Copa Airlines
Sun 5/313:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 2/28![Copa Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 2/26. 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 5/2512:30 am
SJO
- ORD
1 stop8h 50m
United Airlines
Wed 6/172:05 pm
ORD
- SJO
1 stop21h 06m
United Airlines
Deal found 2/26![United Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Wed 5/612:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 2/28![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 2/25. 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.
Thu 4/21:20 pm
SJO
- MDW
1 stop8h 11m
Delta
Thu 4/99:35 am
MDW
- SJO
2 stops12h 40m
Delta
Deal found 2/25![Delta logo]()
$627
This Copa Airlines deal was found by Cheapflights users on 2/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:46 am
SJO
- ORD
1 stop18h 27m
Copa Airlines
Thu 4/308:06 am
ORD
- SJO
1 stop11h 54m
Copa Airlines
Deal found 2/28![Copa Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1912:30 am
SJO
- ORD
1 stop23h 15m
United Airlines
Thu 7/309:21 pm
ORD
- SJO
1 stop23h 16m
United Airlines
Deal found 2/24![United Airlines logo]()
$434
This Copa Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:08 am
SJO
- ORD
1 stop8h 51m
Copa Airlines
Thu 9/38:01 am
ORD
- SJO
1 stop11h 58m
Copa Airlines
Deal found 2/25![Copa Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Sat 4/256:00 am
SJO
- ORD
1 stop13h 46m
United Airlines
Sat 5/27:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Deal found 2/26![United Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 2/26. 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.
Fri 5/19:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Thu 5/712:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Deal found 2/26![Southwest logo]()
$483
This Copa Airlines deal was found by Cheapflights users on 2/26. 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.
Fri 8/710:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Sun 8/163:21 pm
ORD
- SJO
3 stops26h 31m
Copa Airlines
Deal found 2/26![Copa Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Sun 8/212:30 am
SJO
- ORD
1 stop23h 15m
United Airlines
Sat 8/87:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Deal found 2/27![United Airlines logo]()
$484
This Copa Airlines deal was found by Cheapflights users on 2/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/22:20 pm
SJO
- ORD
1 stop9h 53m
Copa Airlines
Sun 4/53:05 pm
ORD
- SJO
3 stops26h 43m
Copa Airlines
Deal found 2/28![Copa Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 2/28. 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.
Wed 7/158:45 am
SJO
- MDW
1 stop8h 30m
Southwest
Sun 7/195:20 am
MDW
- SJO
1 stop6h 40m
Southwest
Deal found 2/28![Southwest logo]()
$586
This Copa Airlines deal was found by Cheapflights users on 2/26. 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.
Sat 8/110:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Sun 8/93:21 pm
ORD
- SJO
3 stops26h 31m
Copa Airlines
Deal found 2/26![Copa Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:45 am
SJO
- MDW
2 stops9h 10m
Southwest
Fri 7/315:10 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 2/24![Southwest logo]()
$617
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Fri 7/3110:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Deal found 2/24![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:45 am
SJO
- MDW
1 stop8h 30m
Southwest
Sun 6/285:20 am
MDW
- SJO
1 stop6h 40m
Southwest
Deal found 2/24![Southwest logo]()
$628
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:45 am
SJO
- MDW
2 stops9h 10m
Southwest
Sat 8/18:10 pm
MDW
- SJO
2 stops23h 30m
Southwest
Deal found 2/24![Southwest logo]()
$633
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Sun 7/55:05 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 2/25![Southwest logo]()
$634
Last-minute flights from San José to ChicagoDiscover last-minute flight deals from San José to Chicago. Data last updated March 1, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Chicago. Data last updated March 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/26. 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 2/282:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Thu 3/56:00 am
MDW
- SJO
1 stop16h 02m
Delta
Deal found 2/26![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/25. 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.
Sat 2/287:00 am
SJO
- MDW
1 stop8h 21m
Delta
Sat 3/79:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/25![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:40 am
SJO
- MDW
1 stop13h 15m
Southwest
Thu 3/56:00 am
MDW
- SJO
1 stop7h 55m
Southwest
Deal found 2/27![Southwest logo]()
$501
This eDestinos deal was found by Cheapflights users on 2/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:58 am
SJO
- MDW
1 stop29h 43m
Multiple Airlines
Mon 3/96:00 am
MDW
- SJO
1 stop10h 17m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$407
This eDestinos deal was found by Cheapflights users on 2/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Thu 3/125:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$358
This eDestinos deal was found by Cheapflights users on 2/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Wed 3/184:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Multiple Airlines
Wed 3/186:36 pm
ORD
- SJO
2 stops41h 06m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Mon 3/166:10 pm
ORD
- SJO
1 stop18h 04m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Mon 3/166:10 pm
ORD
- SJO
1 stop18h 04m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$348
This Mytrip deal was found by Cheapflights users on 2/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:58 am
SJO
- ORD
1 stop9h 33m
Multiple Airlines
Thu 4/94:36 pm
ORD
- SJO
2 stops19h 06m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$332
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Tue 3/315:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$331
This Expedia deal was found by Cheapflights users on 2/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Wed 3/254:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$323
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 March 1, 2026.
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated March 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:38 pm
SJO
- ORD
1 stop31h 39m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$165
This Super.com deal was found by Cheapflights users on 2/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/26![Spirit Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 5/2012:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 5/2012:20 pm
SJO
- ORD
1 stop25h 54m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:32 pm
SJO
- ORD
1 stop10h 01m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Thu 4/1612:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$182
This Flightnetwork deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/24![Spirit Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25![Spirit Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:45 am
SJO
- ORD
1 stop15h 14m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 4/1512:20 pm
SJO
- MDW
2 stops30h 11m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$207
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 March 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Cheapflightsfares) |
One-way from | $165 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $480 |
Good round-trip deal | $424 or less |
Good one-way deal | $217 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 March 1, 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
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 5/27
6:19 pm-2:06 pm
1 stop18h 47m
Chicago O'Hare Intl
Sun 5/31
3:21 pm-9:06 am
1 stop18h 45m
$431
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/23
5:46 am-1:13 am
1 stop18h 27m
Chicago O'Hare Intl
Thu 4/30
8:06 am-7:00 pm
1 stop11h 54m
$431
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 8/20
4:08 am-1:59 pm
1 stop8h 51m
Chicago O'Hare Intl
Thu 9/3
8:01 am-6:59 pm
1 stop11h 58m
$431
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 5/25
12:30 am-10:20 am
1 stop8h 50m
Chicago O'Hare Intl
Wed 6/17
2:05 pm-10:11 am
1 stop21h 06m
$434
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 7/19
12:30 am-12:45 am
1 stop23h 15m
Chicago O'Hare Intl
Thu 7/30
9:21 pm-7:37 pm
1 stop23h 16m
$434
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 8/7
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sun 8/16
3:21 pm-4:52 pm
3 stops26h 31m
$436
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 5/1
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
Wed 5/6
12:15 pm-7:00 pm
1 stop7h 45m
$438
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 4/25
6:00 am-8:46 pm
1 stop13h 46m
Chicago O'Hare Intl
Sat 5/2
7:36 am-11:55 am
Nonstop5h 19m
$438
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/2
2:20 pm-1:13 am
1 stop9h 53m
Chicago O'Hare Intl
Sun 4/5
3:05 pm-4:48 pm
3 stops26h 43m
$462
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/1
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sun 8/9
3:21 pm-4:52 pm
3 stops26h 31m
$471
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 March.
| 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 |
- 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 February 27, 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, May is the cheapest month in which you can book a flight from San José to Chicago (average of $188). Flying from San José to Chicago in March is currently the most expensive (average of $327). 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 March 1, 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.
Weekly flight availability from San José to Chicago
Explore weekly flight availability from San José to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 1, 2026.
The most flights from SJO to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
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 10% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 226 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 Saturday 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 March 1, 2026.
Read through reviews of airlines operating flights from San José to Chicago, such as Southwest, Copa Airlines, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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 locationsLansing
Merrillville
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Other flights to Chicago
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San José and Chicago flights
Browse other San José and Chicago flight options. Last updated on March 1, 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 March 1, 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 March 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$298 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$189 | Average$443 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$249 | Average$474 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$332 | Average$464 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$400 | Average$498 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |