$129+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jul 4 — Jul 111
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 June 4, 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 June 4, 2026.
This Air Canada deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Sun 10/256:30 pm
ORD
- LIR
1 stop19h 25m
Air Canada
Sun 11/12:55 pm
LIR
- ORD
1 stop18h 05m
Air Canada
Deal found 6/3![Air Canada logo]()
$370
This Air Canada deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/266:30 pm
ORD
- LIR
1 stop19h 25m
Air Canada
Sat 10/311:40 pm
LIR
- ORD
1 stop25h 15m
Air Canada
Deal found 6/2![Air Canada logo]()
$383
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Fri 10/306:30 pm
ORD
- LIR
1 stop19h 25m
Air Canada
Tue 11/172:40 pm
LIR
- ORD
1 stop24h 15m
Air Canada
Deal found 6/4![Air Canada logo]()
$401
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:35 am
MDW
- SJO
1 stop9h 05m
Southwest
Sun 6/712:00 pm
SJO
- MDW
1 stop10h 40m
Southwest
Deal found 5/30![Southwest logo]()
$452
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Fri 6/126:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
Sat 6/207:15 am
SJO
- ORD
2 stops23h 45m
Air Canada
Deal found 5/31![Air Canada logo]()
$452
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:20 am
MDW
- SJO
2 stops11h 20m
Southwest
Tue 9/229:00 am
SJO
- MDW
2 stops10h 45m
Southwest
Deal found 5/31![Southwest logo]()
$453
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Sat 6/139:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Tue 6/237:10 am
SJO
- ORD
2 stops23h 40m
Air Canada
Deal found 5/31![Air Canada logo]()
$455
This Expedia deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/14:59 pm
ORD
- SJO
1 stop16h 21m
Frontier
Thu 7/99:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/3![Frontier logo]()
$458
This Viva deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
- SJO
1 stop24h 45m
Viva
Fri 8/72:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 6/2![Viva logo]()
$461
This eDestinos deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/122:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Sun 10/184:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$463
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:02 am
ORD
- SJO
1 stop24h 10m
Copa Airlines
Wed 7/2910:03 am
SJO
- ORD
1 stop16h 57m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$470
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 6/46:04 pm
ORD
- SJO
1 stop27h 31m
Air Canada
Tue 6/97:10 am
SJO
- ORD
1 stop11h 15m
Air Canada
Deal found 6/1![Air Canada logo]()
$473
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 June 4, 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 June 4, 2026.
This Copa Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 11/42:13 pm
ORD
- SJO
1 stop20h 46m
Copa Airlines
Wed 11/116:05 pm
SJO
- ORD
1 stop18h 41m
Copa Airlines
Deal found 5/31![Copa Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Sun 11/295:30 am
ORD
- SJO
1 stop16h 45m
Delta
Sat 12/127:00 am
SJO
- ORD
1 stop11h 32m
Delta
Deal found 6/2![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 10/198:20 pm
MDW
- SJO
1 stop10h 40m
Southwest
Sun 10/251:05 pm
SJO
- MDW
1 stop10h 50m
Southwest
Deal found 5/31![Southwest logo]()
$562
This Flighttix deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 am
ORD
- LIR
1 stop7h 01m
JetBlue
Sun 7/262:00 pm
LIR
- ORD
1 stop17h 50m
JetBlue
Deal found 5/30![JetBlue logo]()
$610
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 11/159:25 am
ORD
- LIR
1 stop9h 12m
United Airlines
Sat 11/212:01 pm
LIR
- ORD
Nonstop5h 19m
United Airlines
Deal found 5/31![United Airlines logo]()
$666
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 8/56:00 am
ORD
- LIR
2 stops25h 37m
Alaska Airlines
Tue 8/116:39 pm
LIR
- ORD
2 stops28h 20m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$856
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/276:29 pm
ORD
- LIR
1 stop18h 06m
American Airlines
Fri 7/32:47 pm
LIR
- ORD
2 stops14h 42m
American Airlines
Deal found 5/30![American Airlines logo]()
$871
This Expedia deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Tue 7/213:43 pm
ORD
- LIR
2 stops15h 54m
Multiple Airlines
Sun 7/262:00 pm
LIR
- ORD
1 stop17h 50m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$917
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/253:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Sat 8/88:45 am
SJO
- ORD
1 stop15h 17m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/315:28 am
ORD
- SJO
1 stop7h 21m
Delta
Mon 9/71:14 pm
SJO
- ORD
1 stop9h 48m
Delta
Deal found 6/4![Delta logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/33:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Thu 7/95:55 pm
SJO
- ORD
1 stop9h 05m
Copa Airlines
Deal found 5/31![Copa Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/268:02 am
ORD
- SJO
1 stop26h 04m
Copa Airlines
Tue 8/44:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 5/31![Copa Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/73:20 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
Sun 10/114:08 am
SJO
- ORD
1 stop19h 49m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Sun 11/155:15 am
MDW
- LIR
1 stop8h 35m
Southwest
Sat 11/213:45 pm
LIR
- MDW
1 stop9h 00m
Southwest
Deal found 5/31![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Mon 9/71:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/4![Delta logo]()
$611
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/311:20 am
ORD
- SJO
1 stop18h 39m
Copa Airlines
Fri 8/710:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:05 am
MDW
- SJO
1 stop6h 55m
Southwest
Sun 8/99:00 am
SJO
- MDW
1 stop13h 30m
Southwest
Deal found 5/30![Southwest logo]()
$653
This Copa Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/241:20 am
ORD
- SJO
1 stop8h 46m
Copa Airlines
Sun 8/210:03 am
SJO
- ORD
1 stop26h 56m
Copa Airlines
Deal found 6/1![Copa Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/175:00 pm
MDW
- SJO
1 stop14h 00m
Southwest
Sat 10/319:00 am
SJO
- MDW
2 stops9h 25m
Southwest
Deal found 6/4![Southwest logo]()
$655
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![United Airlines logo]()
$812
This Copa Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Sun 7/196:17 pm
SJO
- ORD
1 stop8h 43m
Copa Airlines
Deal found 6/1![Copa Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 10/206:00 am
MDW
- LIR
1 stop7h 00m
Delta
Sun 10/251:25 pm
LIR
- MDW
1 stop7h 20m
Delta
Deal found 5/31![Delta logo]()
$726
This Alaska Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Tue 8/48:20 pm
ORD
- LIR
2 stops22h 09m
Alaska Airlines
Wed 8/126:39 pm
LIR
- ORD
3 stops23h 42m
Alaska Airlines
Deal found 5/31![Alaska Airlines logo]()
$886
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/49:05 am
MDW
- SJO
2 stops10h 35m
Southwest
Tue 8/111:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 5/30![Southwest logo]()
$692
This Copa Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:02 am
ORD
- SJO
1 stop25h 19m
Copa Airlines
Sun 7/2610:03 am
SJO
- ORD
1 stop16h 57m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Tue 7/286:00 am
ORD
- LIR
2 stops25h 37m
Alaska Airlines
Tue 8/46:39 pm
LIR
- ORD
3 stops23h 42m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$897
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:45 am
MDW
- SJO
2 stops12h 30m
Southwest
Sun 7/198:45 am
SJO
- MDW
2 stops12h 00m
Southwest
Deal found 5/31![Southwest logo]()
$692
This Copa Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/283:20 pm
ORD
- SJO
1 stop16h 50m
Copa Airlines
Sat 10/105:45 am
SJO
- ORD
1 stop18h 12m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:30 pm
ORD
- LIR
1 stop14h 14m
United Airlines
Thu 7/211:49 am
LIR
- ORD
1 stop10h 30m
United Airlines
Deal found 6/3![United Airlines logo]()
$1,006
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1410:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Wed 7/228:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Deal found 6/3![Southwest logo]()
$711
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated June 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:35 am
MDW
- SJO
1 stop9h 05m
Southwest
Sun 6/712:00 pm
SJO
- MDW
1 stop10h 40m
Southwest
Deal found 5/30![Southwest logo]()
$452
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 6/46:04 pm
ORD
- SJO
1 stop27h 31m
Air Canada
Tue 6/97:10 am
SJO
- ORD
1 stop11h 15m
Air Canada
Deal found 6/1![Air Canada logo]()
$473
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/55:10 am
MDW
- SJO
1 stop8h 35m
Southwest
Sun 6/712:00 pm
SJO
- MDW
1 stop10h 40m
Southwest
Deal found 6/1![Southwest logo]()
$490
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/97:25 am
ORD
- SJO
1 stop15h 35m
Air Canada
Sat 6/137:15 am
SJO
- ORD
2 stops24h 45m
Air Canada
Deal found 5/31![Air Canada logo]()
$476
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Fri 6/126:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
Sat 6/207:15 am
SJO
- ORD
2 stops23h 45m
Air Canada
Deal found 5/31![Air Canada logo]()
$452
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Sat 6/139:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Tue 6/237:10 am
SJO
- ORD
2 stops23h 40m
Air Canada
Deal found 5/31![Air Canada logo]()
$455
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sun 6/148:20 pm
ORD
- SJO
1 stop26h 40m
Air Canada
Sat 6/207:15 am
SJO
- ORD
2 stops23h 45m
Air Canada
Deal found 6/4![Air Canada logo]()
$474
This Expedia deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/14:59 pm
ORD
- SJO
1 stop16h 21m
Frontier
Thu 7/99:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/3![Frontier logo]()
$458
This Copa Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:02 am
ORD
- SJO
1 stop24h 10m
Copa Airlines
Wed 7/158:45 am
SJO
- ORD
1 stop18h 15m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$490
This KAYAK deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/127:00 am
ORD
- LIR
1 stop7h 01m
JetBlue
Wed 7/152:06 pm
LIR
- ORD
1 stop8h 38m
JetBlue
Deal found 6/3![JetBlue logo]()
$449
This Copa Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/228:02 am
ORD
- SJO
1 stop11h 59m
Copa Airlines
Sun 7/265:55 pm
SJO
- ORD
1 stop19h 02m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$480
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/241:20 am
ORD
- SJO
1 stop8h 46m
Copa Airlines
Sun 8/24:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$470
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 June 4, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 5/31![JetBlue logo]()
$129
This Justfly.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$148
This Viva deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 6/111:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 6/1![Viva logo]()
$154
This Viva deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 11/1212:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 6/1![Viva logo]()
$155
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Sun 8/307:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/3![JetBlue logo]()
$173
This Viva deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 11/1512:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 6/3![Viva logo]()
$174
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/99:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 6/4![Air Canada logo]()
$178
This Viva deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 11/2612:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 6/1![Viva logo]()
$182
This Air Canada deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Sat 6/139:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 5/31![Air Canada logo]()
$183
This Air Canada deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 11/301:55 pm
ORD
- LIR
1 stop23h 45m
Air Canada
Deal found 6/3![Air Canada logo]()
$185
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Fri 8/283:45 pm
ORD
- LIR
1 stop21h 05m
Air Canada
Deal found 6/4![Air Canada logo]()
$189
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 11/246:30 pm
ORD
- LIR
1 stop19h 25m
Air Canada
Deal found 6/4![Air Canada logo]()
$190
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 June 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $370 (Air Canada) |
One-way from | $129 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $555 |
Good round-trip deal | $594 or less |
Good one-way deal | $256 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 June 4, 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
Wed 11/4
2:13 pm-10:59 am
1 stop20h 46m
San José Juan Santamaria Intl
Wed 11/11
6:05 pm-12:46 pm
1 stop18h 41m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 7/25
3:21 pm-8:21 am
1 stop18h 00m
San José Juan Santamaria Intl
Sat 8/8
8:45 am-1:02 am
1 stop15h 17m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 7/3
3:21 pm-7:26 am
1 stop17h 05m
San José Juan Santamaria Intl
Thu 7/9
5:55 pm-4:00 am
1 stop9h 05m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 7/26
8:02 am-9:06 am
1 stop26h 04m
San José Juan Santamaria Intl
Tue 8/4
4:08 am-1:02 am
1 stop19h 54m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 10/7
3:20 pm-9:04 am
1 stop18h 44m
San José Juan Santamaria Intl
Sun 10/11
4:08 am-12:57 am
1 stop19h 49m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 7/31
1:20 am-6:59 pm
1 stop18h 39m
San José Juan Santamaria Intl
Fri 8/7
10:03 am-1:02 am
1 stop13h 59m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 7/24
1:20 am-9:06 am
1 stop8h 46m
San José Juan Santamaria Intl
Sun 8/2
10:03 am-1:59 pm
1 stop26h 56m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 7/4
3:21 pm-7:12 am
1 stop16h 51m
San José Juan Santamaria Intl
Sun 7/19
6:17 pm-4:00 am
1 stop8h 43m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 7/20
8:02 am-8:21 am
1 stop25h 19m
San José Juan Santamaria Intl
Sun 7/26
10:03 am-4:00 am
1 stop16h 57m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 9/28
3:20 pm-7:10 am
1 stop16h 50m
San José Juan Santamaria Intl
Sat 10/10
5:45 am-12:57 am
1 stop18h 12m
$490
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 $1,101). 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 June 4, 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 19% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 158 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?
Saturday 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.
How far ahead should I book a flight from Chicago to Costa Rica?
Booking 11 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Costa Rica. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 June 4, 2026.
Read reviews from past customers who have flown Southwest,Delta, andCopa 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
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 June 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Costa Rica
Discover the top 10 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 June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$221 | Average$588 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$303 | Average$480 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$623 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$383 | Average$632 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$849 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$386 | Average$591 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$386 | Average$571 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$518 | Average$644 | FlexibilityNo cancel fee | On-time62% |