$147+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Mar 25 — Apr 11
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 February 23, 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 February 23, 2026.
This CheapOair deal was found by Cheapflights users on 2/18. 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 4/235:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Mon 4/2712:20 pm
SJO
- ORD
1 stop30h 27m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$322
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$323
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Tue 4/76:01 pm
ORD
- SJO
2 stops17h 37m
Multiple Airlines
Tue 4/147:00 am
SJO
- ORD
2 stops27h 22m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:20 pm
ORD
- SJO
2 stops16h 55m
Spirit Airlines
Tue 5/1212:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$325
This Expedia deal was found by Cheapflights users on 2/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Sat 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Mon 3/1612:19 pm
SJO
- ORD
1 stop21h 17m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Wed 5/131:27 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Wed 5/2712:20 pm
SJO
- ORD
1 stop10h 54m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$328
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 2/238:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Tue 3/31:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/19![Spirit Airlines logo]()
$329
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Fri 3/64:44 pm
ORD
- SJO
1 stop18h 46m
Multiple Airlines
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Wed 5/275:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Wed 6/312:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/22![Spirit Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 2/235:15 am
ORD
- SJO
1 stop7h 07m
Multiple Airlines
Wed 2/255:00 am
SJO
- ORD
2 stops28h 39m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sat 4/116:00 am
MDW
- SJO
1 stop29h 42m
Multiple Airlines
Tue 4/287:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$366
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 February 23, 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 February 23, 2026.
This Copa Airlines deal was found by Cheapflights users on 2/19. 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 3/248:34 am
ORD
- SJO
1 stop11h 27m
Copa Airlines
Thu 4/24:09 am
SJO
- ORD
1 stop8h 41m
Copa Airlines
Deal found 2/19![Copa Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/117:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Thu 4/1611:13 am
SJO
- ORD
1 stop12h 32m
United Airlines
Deal found 2/19![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 2/19. 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.
Fri 5/15:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Fri 5/81:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 2/19![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 2/2512:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Tue 3/37:00 am
SJO
- MDW
1 stop15h 33m
Delta
Deal found 2/19![Delta logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Fri 4/104:05 pm
MDW
- LIR
1 stop22h 18m
Multiple Airlines
Tue 4/142:40 pm
LIR
- MDW
1 stop18h 35m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$530
This Copa Airlines deal was found by Cheapflights users on 2/19. 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 3/178:34 am
ORD
- SJO
1 stop11h 27m
Copa Airlines
Tue 3/245:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Deal found 2/19![Copa Airlines logo]()
$336
This Copa Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 4/53:05 pm
ORD
- SJO
1 stop17h 03m
Copa Airlines
Thu 4/98:30 am
SJO
- ORD
1 stop15h 43m
Copa Airlines
Deal found 2/20![Copa Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/187:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Tue 4/217:55 am
SJO
- ORD
1 stop11h 00m
United Airlines
Deal found 2/19![United Airlines logo]()
$435
This Southwest deal was found by Cheapflights users on 2/20. 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 4/1412:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Tue 4/281:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 2/20![Southwest logo]()
$440
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 5/167:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Tue 5/197:55 am
SJO
- ORD
1 stop11h 00m
United Airlines
Deal found 2/19![United Airlines logo]()
$468
This Copa Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/43:05 pm
ORD
- SJO
1 stop17h 20m
Copa Airlines
Thu 4/98:46 am
SJO
- ORD
1 stop15h 27m
Copa Airlines
Deal found 2/19![Copa Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 3/512:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Wed 3/117:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/20![Delta logo]()
$532
This Southwest deal was found by Cheapflights users on 2/19. 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 4/115:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Thu 4/161:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 2/19![Southwest logo]()
$505
This Copa Airlines deal was found by Cheapflights users on 2/19. 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 5/13:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Wed 5/68:47 am
SJO
- ORD
1 stop15h 28m
Copa Airlines
Deal found 2/19![Copa Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 2/21. 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.
Wed 3/119:35 am
MDW
- SJO
2 stops12h 40m
Delta
Wed 3/187:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/21![Delta logo]()
$543
This Southwest deal was found by Cheapflights users on 2/19. 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 5/167:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Tue 5/199:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Deal found 2/19![Southwest logo]()
$506
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/187:35 am
ORD
- SJO
1 stop13h 04m
United Airlines
Tue 3/245:30 am
SJO
- ORD
1 stop15h 08m
United Airlines
Deal found 2/19![United Airlines logo]()
$508
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 5/712:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Mon 5/119:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 2/19![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 4/146:00 am
MDW
- LIR
1 stop7h 00m
Delta
Tue 4/211:25 pm
LIR
- MDW
1 stop8h 03m
Delta
Deal found 2/19![Delta logo]()
$564
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/177:39 am
ORD
- SJO
Nonstop5h 17m
United Airlines
Wed 3/255:30 am
SJO
- ORD
1 stop25h 16m
United Airlines
Deal found 2/19![United Airlines logo]()
$514
This Copa Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 4/63:05 pm
ORD
- SJO
1 stop18h 15m
Copa Airlines
Sat 4/1110:04 am
SJO
- ORD
1 stop14h 09m
Copa Airlines
Deal found 2/19![Copa Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Mon 3/25:45 am
ORD
- SJO
1 stop7h 30m
United Airlines
Fri 3/62:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Deal found 2/18![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 2/19. 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.
Mon 3/235:30 am
ORD
- LIR
1 stop7h 20m
Delta
Mon 3/302:05 pm
LIR
- ORD
1 stop8h 49m
Delta
Deal found 2/19![Delta logo]()
$584
This Southwest deal was found by Cheapflights users on 2/19. 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 5/25:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Thu 5/72:10 pm
LIR
- MDW
2 stops18h 45m
Southwest
Deal found 2/19![Southwest logo]()
$538
This Southwest deal was found by Cheapflights users on 2/19. 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 5/25:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Wed 5/62:10 pm
LIR
- MDW
2 stops14h 15m
Southwest
Deal found 2/19![Southwest logo]()
$538
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/187:35 am
ORD
- LIR
1 stop11h 02m
United Airlines
Tue 3/241:01 pm
LIR
- ORD
Nonstop5h 19m
United Airlines
Deal found 2/19![United Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 3/305:30 am
ORD
- LIR
1 stop7h 20m
Delta
Mon 4/62:05 pm
LIR
- ORD
1 stop8h 49m
Delta
Deal found 2/21![Delta logo]()
$614
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/257:00 am
ORD
- LIR
1 stop9h 08m
United Airlines
Thu 4/23:27 pm
LIR
- ORD
1 stop8h 59m
United Airlines
Deal found 2/19![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 2/21. 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 3/277:59 pm
ORD
- LIR
1 stop15h 31m
Delta
Mon 4/62:05 pm
LIR
- ORD
1 stop8h 49m
Delta
Deal found 2/21![Delta logo]()
$624
This Southwest deal was found by Cheapflights users on 2/22. 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.
Mon 4/205:30 am
MDW
- LIR
2 stops8h 45m
Southwest
Wed 4/222:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 2/22![Southwest logo]()
$568
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated February 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated February 23, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Sat 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$326
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 2/238:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Tue 3/31:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/19![Spirit Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 2/235:15 am
ORD
- SJO
1 stop7h 07m
Multiple Airlines
Wed 2/255:00 am
SJO
- ORD
2 stops28h 39m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Mon 2/238:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Wed 3/47:50 pm
SJO
- ORD
2 stops37h 49m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$338
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Sat 3/712:35 pm
SJO
- ORD
2 stops11h 12m
Spirit Airlines
Deal found 2/20![Spirit Airlines logo]()
$335
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Mon 3/28:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Mon 3/912:31 pm
SJO
- ORD
1 stop21h 05m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Fri 3/64:44 pm
ORD
- SJO
1 stop18h 46m
Multiple Airlines
Mon 3/912:31 pm
SJO
- ORD
1 stop10h 16m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Mon 3/1612:19 pm
SJO
- ORD
1 stop21h 17m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$327
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:58 pm
ORD
- SJO
2 stops22h 08m
Multiple Airlines
Thu 3/127:05 am
SJO
- ORD
1 stop8h 51m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$336
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Mon 3/1612:19 pm
SJO
- ORD
1 stop21h 58m
Spirit Airlines
Deal found 2/19![Spirit Airlines logo]()
$332
This CheapOair deal was found by Cheapflights users on 2/21. 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.
Wed 3/115:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Wed 3/1812:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 2/21![Spirit Airlines logo]()
$337
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 February 23, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated February 23, 2026.
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:45 pm
ORD
- LIR
1 stop21h 45m
Air Canada
Deal found 2/19![Air Canada logo]()
$147
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/68:40 am
ORD
- LIR
1 stop28h 50m
Air Canada
Deal found 2/19![Air Canada logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/1610:55 am
ORD
- SJO
3 stops13h 45m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$155
This CheapOair deal was found by Cheapflights users on 2/20. 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 4/93:21 pm
ORD
- SJO
2 stops44h 21m
Spirit Airlines
Deal found 2/20![Spirit Airlines logo]()
$156
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:05 am
ORD
- LIR
1 stop29h 40m
Air Canada
Deal found 2/19![Air Canada logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Deal found 2/20![Spirit Airlines logo]()
$157
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJO
1 stop9h 02m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Mon 3/27:23 pm
ORD
- SJO
2 stops23h 32m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Sat 2/289:18 am
ORD
- SJO
3 stops14h 12m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Mon 3/96:00 am
MDW
- SJO
3 stops18h 40m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/185:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/19![Spirit Airlines logo]()
$160
This CheapOair deal was found by Cheapflights users on 2/18. 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.
Wed 4/227:55 am
ORD
- SJO
2 stops28h 20m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$161
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 February 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $322 (CheapOair) |
One-way from | $147 (Air Canada) |
Popular in | December |
Cheapest in | September |
Average price | $469 |
Good round-trip deal | $411 or less |
Good one-way deal | $335 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 February 23, 2026.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.
Fly from
Chicago
Fly to
Costa Rica
Route
Depart
Return
Price
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 3/24
8:34 am-7:01 pm
1 stop11h 27m
San José Juan Santamaria Intl
Thu 4/2
4:09 am-1:50 pm
1 stop8h 41m
$336
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 3/17
8:34 am-7:01 pm
1 stop11h 27m
San José Juan Santamaria Intl
Tue 3/24
5:50 am-1:04 am
1 stop18h 14m
$336
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 4/5
3:05 pm-7:08 am
1 stop17h 03m
San José Juan Santamaria Intl
Thu 4/9
8:30 am-1:13 am
1 stop15h 43m
$371
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 4/11
7:36 am-11:55 am
Nonstop5h 19m
San José Juan Santamaria Intl
Thu 4/16
11:13 am-12:45 am
1 stop12h 32m
$404
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 5/1
5:35 am-12:10 pm
1 stop7h 35m
San José Juan Santamaria Intl
Fri 5/8
1:10 pm-9:55 pm
1 stop7h 45m
$428
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 4/4
3:05 pm-7:25 am
1 stop17h 20m
San José Juan Santamaria Intl
Thu 4/9
8:46 am-1:13 am
1 stop15h 27m
$430
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 5/1
3:21 pm-8:21 am
1 stop18h 00m
San José Juan Santamaria Intl
Wed 5/6
8:47 am-1:15 am
1 stop15h 28m
$430
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 4/18
7:36 am-11:55 am
Nonstop5h 19m
San José Juan Santamaria Intl
Tue 4/21
7:55 am-7:55 pm
1 stop11h 00m
$435
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 4/14
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Tue 4/28
1:10 pm-11:05 pm
1 stop8h 55m
$440
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 5/16
7:36 am-11:55 am
Nonstop5h 19m
San José Juan Santamaria Intl
Tue 5/19
7:55 am-7:55 pm
1 stop11h 00m
$468
Showing 1-10 of 60 results
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, May is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $228). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $343). 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 February 23, 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.
Weekly flight availability from Chicago to Costa Rica
Explore weekly flight availability from Chicago to Costa Rica. 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 February 23, 2026.
The most flights from CHI to CR0 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 often are flights from Chicago to Costa Rica delayed?
About 19% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 173 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?
Tuesday tends to have the lowest number of delays on this route, whereas Wednesday 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 11% 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 February 23, 2026.
Read reviews from past customers who have flown Southwest, Copa Airlines, and United 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.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 23, 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 February 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$589 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$227 | Average$375 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$466 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$340 | Average$616 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$385 | Average$635 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$386 | Average$626 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$394 | Average$592 | FlexibilityNo cancel fee | On-time63% |