$153+ Cheap flights from Chicago (CHI) to Costa Rica
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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
May 22 — May 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Costa Rica 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Costa Rica
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Cheapest flights from Chicago to Costa RicaExplore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
This Air Canada deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/206:40 pm
ORD
- LIR
1 stop19h 50m
Air Canada
Thu 4/232:55 pm
LIR
- ORD
1 stop17h 15m
Air Canada
Deal found 4/20![Air Canada logo]()
$386
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Sun 5/311:00 pm
SJO
- ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$428
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:10 am
ORD
- SJO
1 stop8h 05m
Multiple Airlines
Thu 7/169:35 am
SJO
- ORD
1 stop12h 39m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$429
This CheapOair deal was found by Cheapflights users on 4/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:59 pm
ORD
- SJO
2 stops15h 46m
Spirit Airlines
Mon 5/111:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:00 am
ORD
- SJO
1 stop17h 36m
American Airlines
Fri 5/1511:35 pm
SJO
- ORD
1 stop17h 09m
American Airlines
Deal found 4/21![American Airlines logo]()
$432
This CheapOair deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/166:55 am
ORD
- SJO
2 stops26h 25m
Frontier
Mon 7/209:35 am
SJO
- ORD
1 stop12h 39m
Frontier
Deal found 4/20![Frontier logo]()
$433
This Priceline deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Sat 7/256:55 am
ORD
- SJO
2 stops26h 25m
Frontier
Sat 8/19:35 am
SJO
- ORD
1 stop12h 39m
Frontier
Deal found 4/21![Frontier logo]()
$434
This Copa Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/183:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Tue 6/235:57 pm
SJO
- ORD
1 stop19h 09m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/73:44 pm
ORD
- SJO
1 stop21h 01m
Multiple Airlines
Sun 5/101:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:22 am
ORD
- SJO
2 stops12h 45m
American Airlines
Wed 5/206:30 am
SJO
- ORD
1 stop12h 27m
American Airlines
Deal found 4/21![American Airlines logo]()
$437
This Mytrip deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/35:05 am
ORD
- SJO
1 stop7h 28m
Spirit Airlines
Thu 5/141:00 pm
SJO
- ORD
2 stops30h 11m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/47:33 pm
ORD
- SJO
1 stop17h 12m
Multiple Airlines
Sat 6/202:20 am
SJO
- ORD
1 stop20h 35m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$439
Best flights from Chicago to Costa RicaDiscover carefully curated flight deals from Chicago to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
Discover carefully curated flight deals from Chicago to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
This Copa Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/263:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Mon 6/110:05 am
SJO
- ORD
1 stop16h 55m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/186:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Tue 8/251:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 4/20![Southwest logo]()
$476
This Delta deal was found by Cheapflights users on 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:23 am
MDW
- SJO
1 stop7h 52m
Delta
Sat 7/251:16 pm
SJO
- MDW
1 stop7h 59m
Delta
Deal found 4/19![Delta logo]()
$482
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
ORD
- LIR
1 stop10h 19m
United Airlines
Sun 5/241:20 pm
LIR
- ORD
1 stop10h 25m
United Airlines
Deal found 4/21![United Airlines logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:03 pm
ORD
- LIR
2 stops52h 42m
Alaska Airlines
Sun 10/1110:00 am
LIR
- ORD
2 stops36h 41m
Alaska Airlines
Deal found 4/21![Alaska Airlines logo]()
$822
This Copa Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/43:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Fri 6/128:47 am
SJO
- ORD
1 stop18h 13m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$470
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:17 am
MDW
- SJO
2 stops27h 32m
Delta
Wed 6/241:14 pm
SJO
- MDW
2 stops22h 22m
Delta
Deal found 4/17![Delta logo]()
$487
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 6/183:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Tue 6/231:37 pm
SJO
- ORD
1 stop13h 23m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/512:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Fri 5/89:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 4/21![Southwest logo]()
$517
This Copa Airlines deal was found by Cheapflights users on 4/18. 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 6/103:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Tue 6/165:57 pm
SJO
- ORD
1 stop19h 09m
Copa Airlines
Deal found 4/18![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 9/119:20 am
MDW
- SJO
2 stops10h 20m
Southwest
Mon 9/149:00 am
SJO
- MDW
2 stops11h 00m
Southwest
Deal found 4/22![Southwest logo]()
$549
This Copa Airlines deal was found by Cheapflights users on 4/19. 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.
Fri 6/123:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Sat 6/205:47 am
SJO
- ORD
1 stop10h 39m
Copa Airlines
Deal found 4/19![Copa Airlines logo]()
$470
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am
MDW
- SJO
1 stop6h 58m
Delta
Tue 10/201:23 pm
SJO
- MDW
1 stop7h 22m
Delta
Deal found 4/17![Delta logo]()
$585
This Copa Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/113:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Wed 6/175:57 pm
SJO
- ORD
1 stop19h 09m
Copa Airlines
Deal found 4/20![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 4/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:40 pm
MDW
- SJO
2 stops16h 00m
Southwest
Sun 10/251:05 pm
SJO
- MDW
1 stop10h 50m
Southwest
Deal found 4/19![Southwest logo]()
$572
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 10/35:59 pm
MDW
- LIR
2 stops19h 01m
Delta
Fri 10/91:25 pm
LIR
- MDW
1 stop7h 20m
Delta
Deal found 4/21![Delta logo]()
$605
This Copa Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/213:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Sun 5/246:01 pm
SJO
- ORD
1 stop19h 05m
Copa Airlines
Deal found 4/21![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 4/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:30 am
ORD
- LIR
1 stop8h 55m
United Airlines
Sun 8/94:05 pm
LIR
- ORD
1 stop11h 46m
United Airlines
Deal found 4/18![United Airlines logo]()
$777
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:15 am
MDW
- SJO
1 stop8h 20m
Southwest
Fri 5/81:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 4/17![Southwest logo]()
$591
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:58 pm
MDW
- LIR
2 stops18h 02m
Delta
Thu 7/161:25 pm
LIR
- MDW
2 stops18h 43m
Delta
Deal found 4/17![Delta logo]()
$621
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 5/283:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Sun 6/75:57 pm
SJO
- ORD
1 stop9h 03m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$470
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:50 pm
ORD
- LIR
1 stop18h 29m
United Airlines
Thu 7/161:20 pm
LIR
- ORD
1 stop10h 25m
United Airlines
Deal found 4/17![United Airlines logo]()
$786
This Southwest deal was found by Cheapflights users on 4/18. 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.
Sat 5/97:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Sat 7/251:10 pm
SJO
- MDW
2 stops16h 55m
Southwest
Deal found 4/18![Southwest logo]()
$602
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 5/148:02 am
ORD
- SJO
1 stop11h 59m
Copa Airlines
Mon 5/188:47 am
SJO
- ORD
1 stop15h 28m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:05 am
MDW
- SJO
1 stop6h 44m
Delta
Thu 7/161:16 pm
SJO
- MDW
2 stops18h 52m
Delta
Deal found 4/21![Delta logo]()
$639
This United Airlines deal was found by Cheapflights users on 4/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:35 am
ORD
- LIR
1 stop7h 50m
United Airlines
Wed 7/293:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Deal found 4/19![United Airlines logo]()
$802
This Southwest deal was found by Cheapflights users on 4/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Sat 8/151:15 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 4/19![Southwest logo]()
$620
This Copa Airlines deal was found by Cheapflights users on 4/18. 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.
Thu 6/183:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Sun 6/215:57 pm
SJO
- ORD
1 stop9h 03m
Copa Airlines
Deal found 4/18![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 10/107:49 am
ORD
- LIR
Nonstop5h 04m
United Airlines
Sat 10/171:03 pm
LIR
- ORD
Nonstop5h 24m
United Airlines
Deal found 4/20![United Airlines logo]()
$812
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
MDW
- LIR
1 stop7h 00m
Delta
Mon 9/211:25 pm
LIR
- MDW
1 stop7h 21m
Delta
Deal found 4/20![Delta logo]()
$676
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated April 22, 2026 and is based on user searches.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:50 pm
ORD
- SJO
2 stops19h 43m
Spirit Airlines
Fri 5/81:00 pm
SJO
- ORD
3 stops32h 14m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$434
This Mytrip deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/35:05 am
ORD
- SJO
1 stop7h 28m
Spirit Airlines
Thu 5/141:00 pm
SJO
- ORD
2 stops30h 11m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$438
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Sun 5/311:00 pm
SJO
- ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:22 am
ORD
- SJO
2 stops12h 45m
American Airlines
Wed 5/206:30 am
SJO
- ORD
1 stop12h 27m
American Airlines
Deal found 4/21![American Airlines logo]()
$437
This CheapOair deal was found by Cheapflights users on 4/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:59 pm
ORD
- SJO
2 stops15h 46m
Spirit Airlines
Mon 5/111:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/73:44 pm
ORD
- SJO
1 stop21h 01m
Multiple Airlines
Sun 5/101:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$436
This CheapOair deal was found by Cheapflights users on 4/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Fri 5/151:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$440
This Cheapflightsfares deal was found by Cheapflights users on 4/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Sun 5/101:00 pm
SJO
- ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:00 am
ORD
- SJO
1 stop17h 36m
American Airlines
Fri 5/1511:35 pm
SJO
- ORD
1 stop17h 09m
American Airlines
Deal found 4/21![American Airlines logo]()
$432
This CheapOair deal was found by Cheapflights users on 4/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:50 pm
ORD
- SJO
2 stops19h 55m
Spirit Airlines
Fri 5/151:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:44 pm
ORD
- SJO
1 stop21h 01m
Multiple Airlines
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$429
This Copa Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/163:21 pm
ORD
- SJO
1 stop16h 48m
Copa Airlines
Sat 5/232:59 pm
SJO
- ORD
1 stop9h 16m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$435
One-way flights from Chicago to Costa RicaSearch for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This Viva deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Sun 4/262:15 am
ORD
- SJO
1 stop24h 05m
Viva
Deal found 4/21![Viva logo]()
$153
This Expedia deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Thu 7/95:30 pm
ORD
- SJO
1 stop15h 50m
Frontier
Deal found 4/20![Frontier logo]()
$158
This Volaris deal was found by Cheapflights users on 4/19. 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.
Mon 5/182:35 am
ORD
- SJO
1 stop22h 24m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 6/177:52 am
ORD
- SJO
1 stop29h 23m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$166
This FlightHub deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:11 pm
ORD
- SJO
1 stop16h 08m
Frontier
Deal found 4/22![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/107:52 am
ORD
- SJO
1 stop28h 53m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$172
This Super.com deal was found by Cheapflights users on 4/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:55 pm
ORD
- SJO
1 stop17h 24m
Frontier
Deal found 4/18![Frontier logo]()
$174
This CheapOair deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Mon 5/115:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$175
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Sat 6/65:11 pm
ORD
- SJO
1 stop16h 08m
Frontier
Deal found 4/20![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:52 am
ORD
- SJO
1 stop29h 23m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$181
This Viva deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Sun 7/121:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 4/21![Viva logo]()
$182
Find flight deals from Chicago to Costa Rica
Keep the following information in mind while searching for Chicago to Costa Rica flight deals. Data was last updated April 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $428 (Cheapflightsfares) |
One-way from | $153 (Viva) |
Popular in | December |
Cheapest in | September |
Average price | $548 |
Good round-trip deal | $657 or less |
Good one-way deal | $366 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Costa Rica 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 22, 2026.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 5/26
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Mon 6/1
10:05 am-4:00 am
1 stop16h 55m
$465
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 6/4
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Fri 6/12
8:47 am-4:00 am
1 stop18h 13m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 6/18
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Tue 6/23
1:37 pm-4:00 am
1 stop13h 23m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 6/10
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Tue 6/16
5:57 pm-2:06 pm
1 stop19h 09m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 6/12
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Sat 6/20
5:47 am-5:26 pm
1 stop10h 39m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 6/11
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Wed 6/17
5:57 pm-2:06 pm
1 stop19h 09m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 5/21
3:21 pm-8:21 am
1 stop18h 00m
San José Juan Santamaria Intl
Sun 5/24
6:01 pm-2:06 pm
1 stop19h 05m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 5/28
3:21 pm-8:21 am
1 stop18h 00m
San José Juan Santamaria Intl
Sun 6/7
5:57 pm-4:00 am
1 stop9h 03m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 5/14
8:02 am-7:01 pm
1 stop11h 59m
San José Juan Santamaria Intl
Mon 5/18
8:47 am-1:15 am
1 stop15h 28m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 6/18
3:21 pm-7:12 am
1 stop16h 51m
San José Juan Santamaria Intl
Sun 6/21
5:57 pm-4:00 am
1 stop9h 03m
$470
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Costa Rica
Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Chicago with our price prediction graph.
ORD-SJO
MDW-SJO
ORD-LIR
MDW-LIR
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Costa Rica
CHI-CR0
ORD-SJO
MDW-SJO
ORD-LIR
MDW-LIR
What is the cheapest month to book a flight from Chicago to Costa Rica?
Currently, August is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $88). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $1,075). 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 CHI to CR?
Find hourly flight availability from Chicago to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2026.
When flying from Chicago to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to Costa Rica delayed?
About 20% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 160 minutes.
What is the most punctual flight time for Chicago to Costa Rica 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?
Sunday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Costa Rica flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
Reviews of airlines servicing Costa Rica
Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated April 22, 2026.
Read reviews from past customers who have flown Southwest,Copa Airlines, andUnited Airlines from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Costa Rica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Costa Rica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Costa Rica by cabin class
Find flights from Chicago to Costa Rica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Costa Rica flights
Browse other Chicago and Costa Rica flight options. Last updated on April 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chicago to Costa Rica
Discover the top 9 airlines that operate flights from Chicago to Costa Rica. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$380 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$567 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$350 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$303 | Average$473 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$625 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$386 | Average$602 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$387 | Average$626 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$394 | Average$586 | FlexibilityNo cancel fee | On-time63% |