$166+ Cheap flights from Chicago (CHI) to Costa Rica
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.
CHI — SJO
Oct 31 — Nov 71
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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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 October 1, 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 October 1, 2026.
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop16h 49m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/28![Copa Airlines logo]()
$403
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.
Sun 11/110:30 pm -
1 stop10h 20m
Sat 11/71:55 am -
1 stop18h 35m
Deal found 9/29![Avianca logo]()
$404
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.
Fri 10/303:13 pm -
1 stop18h 06m
Thu 11/53:59 am -
1 stop20h 12m
Deal found 9/30![Copa Airlines logo]()
$406
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 12/42:20 pm -
1 stop18h 15m
Sun 12/61:50 am -
1 stop18h 40m
Deal found 9/30![Avianca logo]()
$407
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.
Sat 10/249:20 pm -
1 stop14h 05m
Sat 10/311:05 pm -
Nonstop5h 33m
Deal found 9/30![United Airlines logo]()
$408
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.
Mon 12/72:20 pm -
1 stop18h 15m
Tue 12/225:35 am -
1 stop7h 20m
Deal found 9/30![Avianca logo]()
$409
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/122:20 pm -
1 stop18h 15m
Fri 12/185:35 am -
1 stop7h 20m
Deal found 10/1![Avianca logo]()
$410
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.
Sat 10/317:30 am -
Nonstop5h 18m
Sat 11/72:25 pm -
1 stop9h 01m
Deal found 10/1![United Airlines logo]()
$414
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 11/121:05 pm -
1 stop9h 10m
Mon 11/167:00 am -
1 stop9h 18m
Deal found 9/30![Delta logo]()
$418
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 10/295:27 am -
1 stop7h 33m
Mon 11/22:25 pm -
1 stop9h 32m
Deal found 9/27![Delta logo]()
$418
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.
Thu 11/268:00 am -
1 stop14h 15m
Thu 12/107:00 am -
1 stop13h 53m
Deal found 10/1![Delta logo]()
$419
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:20 pm -
1 stop8h 55m
Tue 1/55:35 am -
1 stop7h 20m
Deal found 9/29![Avianca logo]()
$422
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 October 1, 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 October 1, 2026.
This Copa Airlines 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:13 pm -
1 stop22h 06m
Thu 11/122:18 pm -
1 stop9h 53m
Deal found 9/27![Copa Airlines logo]()
$406
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.
Thu 2/46:50 am -
1 stop11h 26m
Wed 2/101:25 pm -
Nonstop5h 32m
Deal found 9/26![United Airlines logo]()
$425
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.
Tue 2/25:25 am -
1 stop8h 20m
Mon 2/82:45 pm -
1 stop8h 00m
Deal found 9/26![Southwest logo]()
$437
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 11/121:05 pm -
1 stop9h 10m
Mon 11/167:00 am -
1 stop9h 18m
Deal found 9/28![Delta logo]()
$465
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop7h 00m
Sat 11/213:05 pm -
1 stop8h 33m
Deal found 9/30![JetBlue logo]()
$656
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/283:19 pm -
2 stops29h 12m
Wed 2/38:33 am -
2 stops28h 40m
Deal found 9/29![Alaska Airlines logo]()
$673
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.
Sat 11/142:13 pm -
1 stop16h 49m
Wed 11/188:44 am -
1 stop15h 27m
Deal found 9/30![Copa Airlines logo]()
$406
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/282:13 pm -
1 stop17h 09m
Mon 2/15:51 pm -
1 stop18h 55m
Deal found 9/29![Copa Airlines logo]()
$406
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 10/296:04 am -
1 stop6h 56m
Fri 12/42:37 pm -
1 stop8h 17m
Deal found 9/30![Delta logo]()
$465
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.
Sun 1/177:46 am -
Nonstop5h 10m
Fri 1/292:06 pm -
Nonstop5h 23m
Deal found 9/28![United Airlines logo]()
$486
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.
Tue 10/276:04 am -
1 stop6h 41m
Thu 12/32:00 pm -
1 stop8h 54m
Deal found 9/30![Delta logo]()
$500
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 1/1610:30 am -
1 stop7h 46m
Thu 1/211:25 pm -
Nonstop5h 32m
Deal found 9/26![United Airlines logo]()
$517
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 3/35:45 am -
1 stop7h 05m
Mon 3/81:05 pm -
2 stops20h 00m
Deal found 9/30![Southwest logo]()
$587
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/225:59 pm -
2 stops20h 11m
Thu 2/253:25 pm -
2 stops27h 12m
Deal found 9/26![Delta logo]()
$505
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.
Mon 1/255:25 am -
1 stop9h 05m
Sun 1/313:10 pm -
1 stop7h 35m
Deal found 9/28![Southwest logo]()
$610
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.
Sat 2/277:02 am -
Nonstop5h 13m
Sat 3/612:35 pm -
1 stop11h 20m
Deal found 10/1![United Airlines logo]()
$558
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
1 stop6h 58m
Sun 10/252:05 pm -
1 stop8h 52m
Deal found 9/30![JetBlue logo]()
$689
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/222:11 pm -
2 stops30h 20m
Sun 1/318:33 am -
2 stops39h 26m
Deal found 9/30![Alaska Airlines logo]()
$736
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.
Sat 10/317:30 am -
Nonstop5h 18m
Sat 12/52:25 pm -
1 stop8h 31m
Deal found 9/30![United Airlines logo]()
$564
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.
Tue 10/2010:15 am -
1 stop10h 25m
Sun 10/251:35 pm -
1 stop10h 25m
Deal found 9/30![Southwest logo]()
$653
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/225:35 pm -
1 stop19h 00m
Fri 2/261:50 pm -
1 stop18h 59m
Deal found 9/26![Delta logo]()
$599
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.
Mon 1/257:02 am -
Nonstop5h 13m
Sat 1/301:15 am -
1 stop10h 01m
Deal found 9/29![United Airlines logo]()
$564
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/216:00 am -
1 stop6h 45m
Tue 3/21:50 pm -
1 stop18h 59m
Deal found 9/26![Delta logo]()
$599
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.
Sat 10/315:30 am -
1 stop7h 52m
Fri 12/411:28 pm -
1 stop10h 12m
Deal found 9/30![United Airlines logo]()
$568
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.
Sat 1/306:00 am -
1 stop6h 45m
Thu 2/42:00 pm -
1 stop8h 10m
Deal found 9/29![Delta logo]()
$608
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.
Fri 2/57:02 am -
Nonstop5h 13m
Thu 2/111:25 pm -
Nonstop5h 32m
Deal found 9/30![United Airlines logo]()
$571
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 12/108:55 pm -
2 stops16h 55m
Tue 12/152:45 pm -
2 stops15h 00m
Deal found 9/29![Southwest logo]()
$775
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/196:00 am -
1 stop8h 10m
Thu 2/253:25 pm -
2 stops21h 08m
Deal found 9/26![Delta logo]()
$613
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.
Fri 1/296:00 pm -
1 stop12h 25m
Fri 2/51:25 pm -
Nonstop5h 32m
Deal found 9/26![United Airlines logo]()
$575
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.
Thu 1/285:25 am -
1 stop9h 05m
Fri 1/293:25 pm -
2 stops18h 50m
Deal found 9/28![Southwest logo]()
$775
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated October 1, 2026 and is based on user searches.
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:20 pm -
1 stop10h 30m
Mon 10/269:30 am -
1 stop11h 00m
Deal found 9/30![Avianca logo]()
$424
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.
Sat 10/249:20 pm -
1 stop14h 05m
Sat 10/311:05 pm -
Nonstop5h 33m
Deal found 9/30![United Airlines logo]()
$408
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 10/295:27 am -
1 stop7h 33m
Sun 11/12:25 pm -
1 stop9h 32m
Deal found 9/27![Delta logo]()
$418
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.
Fri 10/303:13 pm -
1 stop18h 06m
Thu 11/53:59 am -
1 stop20h 12m
Deal found 9/30![Copa Airlines logo]()
$406
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:13 pm -
1 stop16h 51m
Thu 11/52:18 pm -
1 stop9h 53m
Deal found 10/1![Copa Airlines logo]()
$407
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop16h 49m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/28![Copa Airlines logo]()
$403
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.
Sat 10/317:30 am -
Nonstop5h 18m
Sat 11/72:25 pm -
1 stop9h 01m
Deal found 10/1![United Airlines logo]()
$414
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.
Sun 11/110:30 pm -
1 stop10h 20m
Sat 11/71:55 am -
1 stop18h 35m
Deal found 9/29![Avianca logo]()
$404
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 11/121:05 pm -
1 stop9h 10m
Mon 11/167:00 am -
1 stop9h 18m
Deal found 9/30![Delta logo]()
$418
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:30 am -
2 stops12h 20m
Fri 11/2012:37 am -
1 stop17h 50m
Deal found 9/30![American Airlines logo]()
$423
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.
Thu 11/268:00 am -
1 stop14h 15m
Thu 12/107:00 am -
1 stop13h 53m
Deal found 10/1![Delta logo]()
$419
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:30 pm -
1 stop26h 00m
Mon 11/305:15 pm -
1 stop27h 15m
Deal found 9/30![Avianca logo]()
$427
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 October 1, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/912:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$166
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/212:53 pm -
1 stop11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$179
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/181:29 pm -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$183
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop13h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$190
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/211:29 pm -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$191
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 1/275:25 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$205
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/301:55 pm -
1 stop24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Air Canada logo]()
$208
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:40 pm -
2 stops22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$216
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:03 am -
1 stop31h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$218
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.
Fri 11/273:40 pm -
2 stops22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Air Canada logo]()
$221
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/49:00 am -
Nonstop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![American Airlines logo]()
$230
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.
Mon 10/265:27 am -
1 stop7h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$234
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 October 1, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $403 (Booking.com) |
One-way from | $166 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $454 |
Good round-trip deal | $507 or less |
Good one-way deal | $410 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 7,457,451 searches. Data last updated October 1, 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
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 1/27
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$205
Quickest round-trip
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Mon 2/8
7:46 am-12:56 pm
Nonstop5h 10m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Tue 10/27
1:55 pm-11:45 am
2 stops22h 50m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Wed 12/30
7:40 am-6:37 pm
1 stop10h 57m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Wed 3/24
5:30 am-1:10 pm
1 stop8h 40m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Sun 12/6
6:41 pm-12:45 pm
2 stops18h 04m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Tue 12/29
6:29 pm-11:24 am
1 stop16h 55m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$299
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Fri 11/13
6:30 pm-12:15 pm
2 stops17h 45m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$312
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Fri 1/15
7:20 pm-12:45 pm
2 stops17h 25m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$318
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Fri 11/27
7:00 am-2:00 pm
1 stop7h 00m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$322
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, February is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $518). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $744). 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 October 1, 2026.
When flying from Chicago to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to Costa Rica delayed?
About 20% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 151 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 15% of flights being delayed.
How far ahead should I book a flight from Chicago to Costa Rica?
Booking 24 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 October 1, 2026.
Read reviews from past customers who have flown Southwest,Copa Airlines, andUnited Airlines from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 October 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 9 airlines flying from Chicago to Costa Rica
Discover the top 9 airlines that operate flights from Chicago to Costa Rica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$565 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$303 | Average$516 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$324 | Average$578 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$333 | Average$625 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$364 | Average$591 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$371 | Average$616 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$382 | Average$662 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$825 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$395 | Average$658 | FlexibilityNo cancel fee | On-time63% |