$201+ Cheap flights from Costa Rica to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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Find cheap flights from Costa Rica to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Costa Rica to Chicago
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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 October 1, 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 October 1, 2026.
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:50 am -
1 stop18h 40m
Sat 11/1410:30 pm -
1 stop10h 20m
Deal found 9/30![Avianca logo]()
$381
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:25 am -
1 stop10h 55m
Tue 10/2011:20 pm -
1 stop10h 30m
Deal found 9/30![Avianca logo]()
$382
This Copa Airlines deal was found by Cheapflights users on 9/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:03 am -
1 stop26h 43m
Sat 10/313:13 pm -
1 stop18h 06m
Deal found 9/30![Copa Airlines logo]()
$384
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:50 am -
1 stop18h 40m
Mon 1/42:20 pm -
1 stop18h 15m
Deal found 9/30![Avianca logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/311:05 pm -
Nonstop5h 33m
Sat 11/77:55 pm -
1 stop15h 30m
Deal found 9/29![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:37 pm -
1 stop8h 17m
Sun 11/159:30 am -
2 stops12h 45m
Deal found 9/27![Delta logo]()
$387
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:35 am -
1 stop7h 20m
Thu 1/72:20 pm -
1 stop8h 55m
Deal found 9/30![Avianca logo]()
$387
This Delta deal was found by Cheapflights users on 10/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:25 pm -
2 stops19h 07m
Thu 11/121:05 pm -
1 stop9h 10m
Deal found 10/1![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 10/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:15 am -
1 stop20h 20m
Tue 12/299:43 pm -
1 stop24h 49m
Deal found 10/1![United Airlines logo]()
$388
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:35 am -
1 stop7h 20m
Wed 12/302:20 pm -
1 stop18h 15m
Deal found 9/30![Avianca logo]()
$392
This Avianca deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/225:35 am -
1 stop7h 20m
Wed 1/62:20 pm -
1 stop8h 55m
Deal found 9/29![Avianca logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:40 am -
1 stop18h 40m
Mon 10/511:20 pm -
1 stop10h 30m
Deal found 9/26![Avianca logo]()
$394
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 October 1, 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 October 1, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/41:55 pm -
1 stop19h 50m
Sun 11/89:35 pm -
1 stop13h 50m
Deal found 9/29![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 9/30. 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.
Wed 11/42:15 pm -
1 stop8h 55m
Sun 11/85:15 am -
1 stop7h 05m
Deal found 9/30![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/22:37 pm -
1 stop8h 17m
Sun 12/66:00 am -
1 stop7h 12m
Deal found 9/29![Delta logo]()
$568
This United Airlines deal was found by Cheapflights users on 9/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:28 pm -
1 stop13h 41m
Sat 11/77:55 pm -
1 stop15h 30m
Deal found 9/30![United Airlines logo]()
$387
This JetBlue deal was found by Cheapflights users on 9/26. 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 10/182:05 pm -
1 stop8h 25m
Tue 10/207:00 am -
1 stop6h 58m
Deal found 9/26![JetBlue logo]()
$828
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:30 pm -
1 stop20h 30m
Thu 10/223:20 pm -
1 stop22h 05m
Deal found 9/26![Multiple Airlines logo]()
$900
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:25 pm -
Nonstop5h 32m
Tue 1/1912:40 pm -
1 stop7h 59m
Deal found 9/26![United Airlines logo]()
$451
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:45 pm -
2 stops18h 40m
Mon 11/305:10 am -
1 stop8h 40m
Deal found 9/28![Southwest logo]()
$572
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:45 am -
1 stop11h 09m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 9/26![United Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:15 pm -
1 stop8h 55m
Mon 11/235:15 am -
1 stop7h 05m
Deal found 9/26![Southwest logo]()
$588
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
1 stop9h 18m
Wed 11/251:05 pm -
1 stop9h 10m
Deal found 9/30![Delta logo]()
$649
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/152:20 pm -
1 stop10h 23m
Mon 1/185:30 pm -
1 stop18h 24m
Deal found 9/29![United Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:25 pm -
1 stop8h 08m
Wed 11/119:30 am -
2 stops12h 45m
Deal found 9/28![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:25 pm -
1 stop7h 29m
Sat 11/286:00 am -
1 stop8h 10m
Deal found 9/28![Delta logo]()
$654
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:15 am -
1 stop23h 28m
Mon 1/257:02 am -
Nonstop5h 13m
Deal found 9/28![United Airlines logo]()
$546
This Southwest deal was found by Cheapflights users on 9/30. 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 3/203:00 pm -
2 stops19h 25m
Sun 3/288:00 am -
2 stops12h 40m
Deal found 9/30![Southwest logo]()
$688
This JetBlue deal was found by Cheapflights users on 9/26. 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 10/182:05 pm -
1 stop8h 25m
Wed 10/217:00 am -
1 stop6h 58m
Deal found 9/26![JetBlue logo]()
$841
This Delta deal was found by Cheapflights users on 9/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:25 pm -
1 stop8h 08m
Sun 11/86:04 am -
1 stop6h 56m
Deal found 9/30![Delta logo]()
$657
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/221:25 pm -
Nonstop5h 32m
Wed 12/305:30 am -
1 stop15h 09m
Deal found 9/29![United Airlines logo]()
$549
This JetBlue deal was found by Cheapflights users on 9/26. 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 10/182:05 pm -
1 stop8h 25m
Thu 10/227:00 am -
1 stop6h 58m
Deal found 9/26![JetBlue logo]()
$841
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:00 am -
1 stop8h 35m
Mon 10/1911:50 am -
1 stop8h 50m
Deal found 9/27![Southwest logo]()
$698
This United Airlines deal was found by Cheapflights users on 9/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:28 pm -
1 stop24h 33m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 9/30![United Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:25 pm -
2 stops19h 14m
Sat 11/285:30 am -
1 stop8h 40m
Deal found 9/28![Delta logo]()
$703
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/241:15 am -
1 stop10h 01m
Sun 1/317:02 am -
Nonstop5h 13m
Deal found 9/26![United Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 10/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:05 am -
1 stop15h 05m
Sun 1/319:30 am -
2 stops12h 35m
Deal found 10/1![Delta logo]()
$708
This Southwest deal was found by Cheapflights users on 10/1. 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.
Thu 12/172:45 pm -
1 stop10h 20m
Tue 12/225:10 am -
1 stop8h 40m
Deal found 10/1![Southwest logo]()
$806
This United Airlines deal was found by Cheapflights users on 9/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:25 pm -
Nonstop5h 32m
Sat 1/29:43 pm -
1 stop20h 33m
Deal found 9/30![United Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/132:10 pm -
1 stop8h 00m
Wed 1/201:00 pm -
2 stops9h 05m
Deal found 9/28![Delta logo]()
$708
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:00 pm -
2 stops22h 51m
Sat 11/286:00 am -
1 stop8h 10m
Deal found 9/28![Delta logo]()
$708
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:20 pm -
1 stop15h 42m
Sat 11/287:46 am -
Nonstop5h 10m
Deal found 9/28![United Airlines logo]()
$624
Last-minute flights from Costa Rica to ChicagoDiscover last-minute flight deals from Costa Rica to Chicago. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Chicago. Data last updated October 1, 2026 and is based on user searches.
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:25 am -
1 stop10h 55m
Tue 10/2011:20 pm -
1 stop10h 30m
Deal found 9/30![Avianca logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:55 am -
1 stop14h 32m
Thu 10/299:35 pm -
1 stop15h 47m
Deal found 9/28![United Airlines logo]()
$387
This Copa Airlines deal was found by Cheapflights users on 9/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:03 am -
1 stop26h 43m
Sat 10/313:13 pm -
1 stop18h 06m
Deal found 9/30![Copa Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/311:05 pm -
Nonstop5h 33m
Sat 11/77:55 pm -
1 stop15h 30m
Deal found 9/29![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 10/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:25 pm -
2 stops19h 07m
Thu 11/121:05 pm -
1 stop9h 10m
Deal found 10/1![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 10/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:25 pm -
1 stop9h 01m
Thu 11/127:29 am -
1 stop13h 10m
Deal found 10/1![United Airlines logo]()
$388
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:50 am -
1 stop18h 40m
Sat 11/1410:30 pm -
1 stop10h 20m
Deal found 9/30![Avianca logo]()
$381
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:37 pm -
1 stop8h 17m
Sun 11/159:30 am -
2 stops12h 45m
Deal found 9/27![Delta logo]()
$387
This Avianca deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:30 am -
1 stop11h 00m
Thu 12/1010:30 pm -
1 stop10h 20m
Deal found 9/28![Avianca logo]()
$397
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/218:45 am -
1 stop11h 09m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 9/29![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/213:03 pm -
1 stop16h 32m
Sat 11/286:00 am -
1 stop8h 51m
Deal found 9/29![American Airlines logo]()
$396
This Avianca deal was found by Cheapflights users on 9/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:50 am -
1 stop18h 40m
Mon 1/42:20 pm -
1 stop18h 15m
Deal found 9/30![Avianca logo]()
$385
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 October 1, 2026.
Search for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This Volaris deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/94:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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.
Sat 10/179:45 am -
1 stop20h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$205
This Trip.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/252:10 pm -
1 stop28h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$223
This Booking.com deal was found by Cheapflights users on 9/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/104:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$227
This Viva deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/192:40 am -
1 stop20h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Viva logo]()
$233
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/221:30 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$239
This Expedia deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:20 pm -
1 stop23h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Air Canada logo]()
$242
This Volaris deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/64:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$244
This Travelocity deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:10 pm -
1 stop18h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Air Canada logo]()
$247
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:10 pm -
2 stops19h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Air Canada logo]()
$250
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:10 pm -
2 stops23h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Air Canada logo]()
$255
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/191:30 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$257
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 October 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Avianca) |
One-way from | $201 (Volaris) |
Popular in | July |
Cheapest in | January |
Average price | $496 |
Good round-trip deal | $386 or less |
Good one-way deal | $375 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 7,457,451 searches. Data last updated October 1, 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 Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Sat 10/24
1:00 pm-9:23 am
1 stop19h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$223
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 10/22
1:30 pm-10:20 pm
1 stop7h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$239
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 12/6
4:15 pm-11:13 am
1 stop18h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 12/17
1:20 pm-10:55 pm
1 stop9h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$257
Quickest round-trip
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Tue 12/22
12:30 pm-5:53 pm
Nonstop5h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Tue 12/22
2:00 pm-10:22 pm
1 stop8h 22m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Thu 12/24
3:25 pm-9:13 am
1 stop17h 48m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Fri 12/11
5:20 pm-7:45 am
1 stop14h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Tue 12/29
3:25 pm-8:52 am
1 stop17h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Thu 12/3
2:20 pm-4:30 pm
1 stop26h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
Showing 1-10 of 60 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.
SJO-ORD
SJO-MDW
LIR-ORD
LIR-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
SJO-ORD
SJO-MDW
LIR-ORD
LIR-MDW
What is the cheapest month to book a flight from Costa Rica to Chicago?
Currently, January is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $389). Flying from Costa Rica to Chicago in July is currently the most expensive (average of $640). 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 October 1, 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 7% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 197 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 5% of flights being delayed.
How far ahead should I book a flight from Costa Rica to Chicago?
Booking 89 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 October 1, 2026.
Read reviews from past customers who have flown Southwest,Copa Airlines, andUnited 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
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
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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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 October 1, 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 October 1, 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 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$453 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$516 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$487 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$632 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$390 | Average$697 | FlexibilityNo cancel fee | On-time63% |