$166+ Cheap flights from Costa Rica to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jul 26 — Aug 21
Round-trip
1 adult, Economy
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Find cheap flights from Costa Rica to Chicago with Cheapflights
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Cheapest flights from Costa Rica to ChicagoExplore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 26, 2026.
Explore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 26, 2026.
This Justfly.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Mon 9/216:00 am
ORD
- LIR
1 stop6h 57m
JetBlue
Deal found 6/26![JetBlue logo]()
$294
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Sat 10/36:00 am
ORD
- LIR
1 stop6h 57m
JetBlue
Deal found 6/23![JetBlue logo]()
$314
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Mon 9/2810:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 6/24![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/79:00 am
SJO
- MDW
1 stop9h 20m
Southwest
Mon 10/128:50 pm
MDW
- SJO
2 stops15h 50m
Southwest
Deal found 6/23![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Tue 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 6/25![Southwest logo]()
$383
This SmartFares deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Sun 8/307:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/23![JetBlue logo]()
$386
This Air Canada deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:10 pm
LIR
- ORD
1 stop28h 33m
Air Canada
Sat 11/77:03 am
ORD
- LIR
1 stop31h 07m
Air Canada
Deal found 6/24![Air Canada logo]()
$388
This SmartFares deal was found by Cheapflights users on 6/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Mon 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/21![JetBlue logo]()
$399
This Southwest deal was found by Cheapflights users on 6/22. 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.
Tue 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Tue 9/86:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/22![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/51:15 pm
SJO
- MDW
1 stop7h 45m
Southwest
Tue 9/810:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 6/23![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Tue 10/66:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Deal found 6/23![Southwest logo]()
$409
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Tue 9/86:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/23![Southwest logo]()
$410
Best flights from Costa Rica to ChicagoDiscover carefully curated flight deals from Costa Rica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 26, 2026.
Discover carefully curated flight deals from Costa Rica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 26, 2026.
This JetBlue deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Mon 10/56:00 am
ORD
- LIR
1 stop6h 57m
JetBlue
Deal found 6/25![JetBlue logo]()
$294
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Wed 9/306:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/23![Southwest logo]()
$411
This Volaris deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Mon 9/72:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/222:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Sat 1/27:45 am
ORD
- SJO
1 stop10h 31m
United Airlines
Deal found 6/22![United Airlines logo]()
$491
This Copa Airlines deal was found by Cheapflights users on 6/22. 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.
Sun 11/110:26 am
SJO
- ORD
1 stop26h 20m
Copa Airlines
Thu 11/52:13 pm
ORD
- SJO
1 stop18h 06m
Copa Airlines
Deal found 6/22![Copa Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 6/21. 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.
Thu 9/241:19 pm
SJO
- MDW
1 stop8h 26m
Delta
Sun 9/276:05 am
MDW
- SJO
1 stop6h 49m
Delta
Deal found 6/21![Delta logo]()
$597
This Air Canada deal was found by Cheapflights users on 6/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/232:40 pm
LIR
- ORD
2 stops24h 16m
Air Canada
Thu 12/318:00 am
ORD
- LIR
1 stop29h 55m
Air Canada
Deal found 6/22![Air Canada logo]()
$685
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Fri 8/212:15 pm
LIR
- ORD
1 stop18h 29m
American Airlines
Mon 9/216:00 am
ORD
- LIR
1 stop8h 18m
American Airlines
Deal found 6/23![American Airlines logo]()
$723
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sat 9/1910:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 6/25![Southwest logo]()
$437
This Copa Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:08 am
SJO
- ORD
1 stop19h 49m
Copa Airlines
Fri 10/93:20 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
Deal found 6/25![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sun 8/303:21 pm
ORD
- SJO
1 stop20h 37m
Copa Airlines
Deal found 6/23![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/21. 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.
Sun 8/94:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sun 8/233:21 pm
ORD
- SJO
1 stop16h 49m
Copa Airlines
Deal found 6/21![Copa Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2312:30 pm
LIR
- ORD
Nonstop5h 19m
United Airlines
Thu 12/316:00 am
ORD
- LIR
1 stop10h 08m
United Airlines
Deal found 6/24![United Airlines logo]()
$644
This Copa Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 8/225:45 am
SJO
- ORD
1 stop18h 17m
Copa Airlines
Sun 8/308:02 am
ORD
- SJO
1 stop24h 08m
Copa Airlines
Deal found 6/21![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/141:40 pm
SJO
- MDW
1 stop7h 35m
Southwest
Thu 8/2010:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 6/23![Southwest logo]()
$636
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/241:20 pm
LIR
- ORD
1 stop29h 45m
United Airlines
Sat 10/37:49 am
ORD
- LIR
Nonstop5h 04m
United Airlines
Deal found 6/23![United Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Mon 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 6/22![Delta logo]()
$717
This Copa Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Fri 9/253:20 pm
ORD
- SJO
1 stop20h 38m
Copa Airlines
Deal found 6/23![Copa Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 6/21. 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 8/221:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Mon 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 6/21![Delta logo]()
$717
This Copa Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Mon 8/318:02 am
ORD
- SJO
1 stop11h 57m
Copa Airlines
Deal found 6/24![Copa Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/72:47 pm
LIR
- ORD
2 stops14h 51m
American Airlines
Tue 7/288:54 pm
ORD
- LIR
1 stop15h 36m
American Airlines
Deal found 6/21![American Airlines logo]()
$829
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:45 am
SJO
- MDW
2 stops10h 55m
Southwest
Tue 7/289:30 am
MDW
- SJO
2 stops11h 10m
Southwest
Deal found 6/25![Southwest logo]()
$713
This Copa Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/2410:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Wed 9/308:01 am
ORD
- SJO
1 stop25h 18m
Copa Airlines
Deal found 6/23![Copa Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/291:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Fri 9/116:05 am
MDW
- SJO
1 stop6h 49m
Delta
Deal found 6/23![Delta logo]()
$752
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 11/55:20 pm
LIR
- ORD
1 stop14h 11m
United Airlines
Sat 11/77:46 am
ORD
- LIR
Nonstop5h 10m
United Airlines
Deal found 6/23![United Airlines logo]()
$757
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Fri 8/2110:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 6/23![Southwest logo]()
$718
This Copa Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:59 am
SJO
- ORD
1 stop8h 47m
Copa Airlines
Mon 11/92:13 pm
ORD
- SJO
1 stop20h 46m
Copa Airlines
Deal found 6/25![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/119:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Wed 8/196:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/23![Southwest logo]()
$739
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sun 8/2310:15 am
MDW
- SJO
2 stops9h 25m
Southwest
Deal found 6/24![Southwest logo]()
$746
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:45 am
SJO
- MDW
2 stops12h 00m
Southwest
Sat 7/255:05 am
MDW
- SJO
1 stop9h 30m
Southwest
Deal found 6/24![Southwest logo]()
$754
Last-minute flights from Costa Rica to ChicagoDiscover last-minute flight deals from Costa Rica to Chicago. Data last updated June 26, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Chicago. Data last updated June 26, 2026 and is based on user searches.
This Faresmojo deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:00 pm
LIR
- ORD
1 stop30h 03m
JetBlue
Thu 7/307:00 am
ORD
- LIR
1 stop7h 01m
JetBlue
Deal found 6/24![JetBlue logo]()
$504
This eDestinos deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:10 pm
SJO
- ORD
1 stop23h 45m
Avianca
Sat 7/118:43 am
ORD
- SJO
1 stop24h 47m
Avianca
Deal found 6/23![Avianca logo]()
$489
This Justfly.com deal was found by Cheapflights users on 6/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:10 pm
SJO
- ORD
1 stop23h 45m
Avianca
Tue 7/148:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/21![Avianca logo]()
$477
This CheapOair deal was found by Cheapflights users on 6/21. 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.
Fri 7/172:02 pm
SJO
- ORD
1 stop8h 42m
Multiple Airlines
Fri 7/315:13 pm
ORD
- SJO
1 stop16h 17m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$488
This Mytrip deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:45 am
SJO
- ORD
1 stop12h 25m
Frontier
Sat 7/255:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 6/25![Frontier logo]()
$486
This Travelocity deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:00 pm
LIR
- ORD
1 stop19h 00m
Multiple Airlines
Sat 7/257:00 am
ORD
- LIR
1 stop7h 01m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$560
This Avianca deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:45 pm
SJO
- ORD
2 stops10h 42m
Avianca
Sat 7/255:15 pm
ORD
- SJO
1 stop16h 30m
Avianca
Deal found 6/24![Avianca logo]()
$454
This eDestinos deal was found by Cheapflights users on 6/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Sun 7/261:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$465
This Booking.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Wed 7/295:13 pm
ORD
- SJO
1 stop16h 07m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$478
This eDestinos deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 7/281:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$481
This Frontier deal was found by Cheapflights users on 6/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:45 am
SJO
- MDW
2 stops11h 18m
Frontier
Wed 7/294:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Deal found 6/22![Frontier logo]()
$569
This Copa Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/298:45 am
SJO
- ORD
1 stop18h 15m
Copa Airlines
Sun 8/23:21 pm
ORD
- SJO
1 stop18h 43m
Copa Airlines
Deal found 6/23![Copa Airlines logo]()
$494
One-way flights from Costa Rica to ChicagoSearch for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated June 26, 2026.
Search for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated June 26, 2026.
This JetBlue deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Deal found 6/26![JetBlue logo]()
$166
This SmartFares deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 6/25![JetBlue logo]()
$171
This JetBlue deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Deal found 6/26![JetBlue logo]()
$196
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 6/23![Southwest logo]()
$213
This Viva deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/242:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 6/24![Viva logo]()
$218
This SmartFares deal was found by Cheapflights users on 6/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:05 pm
SJO
- ORD
1 stop9h 26m
JetBlue
Deal found 6/21![JetBlue logo]()
$231
This SmartFares deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 6/23![JetBlue logo]()
$236
This Booking.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:00 pm
LIR
- ORD
1 stop29h 35m
Air Canada
Deal found 6/24![Air Canada logo]()
$236
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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.
Thu 7/232:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/21![JetBlue logo]()
$238
This Volaris deal was found by Cheapflights users on 6/22. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$242
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:05 pm
LIR
- ORD
1 stop9h 26m
JetBlue
Deal found 6/23![JetBlue logo]()
$251
This Orbitz deal was found by Cheapflights users on 6/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/222:55 pm
LIR
- ORD
1 stop22h 01m
Air Canada
Deal found 6/22![Air Canada logo]()
$252
Find flight deals from Costa Rica to Chicago
Keep the following information in mind while searching for Costa Rica to Chicago flight deals. Data was last updated June 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $314 (JetBlue) |
One-way from | $166 (JetBlue) |
Popular in | June |
Cheapest in | January |
Average price | $561 |
Good round-trip deal | $701 or less |
Good one-way deal | $353 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Costa Rica to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 26, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LiberiaChicago
LIR - ORD
LIRORD
Liberia
Fri 10/2
1:05 pm-11:31 pm
1 stop9h 26m
Chicago O'Hare Intl
Mon 10/5
6:00 am-11:57 am
1 stop6h 57m
$294
Quickest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 9/24
1:40 pm-10:15 pm
1 stop7h 35m
Chicago Midway
Wed 9/30
6:15 am-12:45 pm
1 stop7h 30m
$411
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 9/15
1:40 pm-11:10 pm
1 stop8h 30m
Chicago Midway
Sat 9/19
10:25 am-6:00 pm
1 stop8h 35m
$437
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 9/3
4:15 pm-12:09 pm
1 stop18h 54m
Chicago O'Hare Intl
Mon 9/7
2:53 am-11:59 pm
1 stop22h 06m
$483
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 12/22
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Sat 1/2
7:45 am-6:16 pm
1 stop10h 31m
$491
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 11/1
10:26 am-12:46 pm
1 stop26h 20m
Chicago O'Hare Intl
Thu 11/5
2:13 pm-8:19 am
1 stop18h 06m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 10/2
4:08 am-12:57 am
1 stop19h 49m
Chicago O'Hare Intl
Fri 10/9
3:20 pm-9:04 am
1 stop18h 44m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/25
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Sun 8/30
3:21 pm-10:58 am
1 stop20h 37m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 8/9
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Sun 8/23
3:21 pm-7:10 am
1 stop16h 49m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/22
5:45 am-1:02 am
1 stop18h 17m
Chicago O'Hare Intl
Sun 8/30
8:02 am-7:10 am
1 stop24h 08m
$494
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Costa Rica to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Costa Rica with our price prediction graph.
LIR-ORD
SJO-ORD
SJO-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Costa Rica to Chicago
CR0-CHI
LIR-ORD
SJO-ORD
SJO-MDW
What is the cheapest month to book a flight from Costa Rica to Chicago?
Currently, April is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $103). Flying from Costa Rica to Chicago in July is currently the most expensive (average of $291). 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 CR to CHI?
Find hourly flight availability from Costa Rica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 26, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Costa Rica to Chicago as you normally would.
How often are flights from Costa Rica to Chicago delayed?
About 9% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 192 minutes.
What is the most punctual flight time for Costa Rica to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Costa Rica to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
How far ahead should I book a flight from Costa Rica to Chicago?
Booking 29 days in advance of your planned departure date is, on average, the best time to get cheap flights from Costa Rica to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 26, 2026.
Read reviews from past customers who have flown Southwest,Delta, andCopa Airlines from Costa Rica to Chicago. 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
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Costa Rica to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Costa Rica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 26, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Costa Rica to Chicago by cabin class
Find flights from Costa Rica to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Costa Rica and Chicago flights
Browse other Costa Rica and Chicago flight options. Last updated on June 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Costa Rica to Chicago
Discover the top 5 airlines that operate flights from Costa Rica to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$493 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$513 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$367 | Average$633 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$472 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$390 | Average$507 | FlexibilityNo cancel fee | On-time63% |