$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
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Costa Rica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 5, 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 5, 2026.
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:40 pm -
1 stop22h 40m
Thu 12/103:20 pm -
1 stop19h 47m
Deal found 10/4![Air Canada logo]()
$360
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm -
2 stops17h 40m
Tue 11/173:20 pm -
1 stop23h 42m
Deal found 10/4![Air Canada logo]()
$368
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/1210:57 am -
2 stops27h 13m
Thu 11/193:20 pm -
1 stop23h 40m
Deal found 10/5![Air Canada logo]()
$370
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:40 pm -
2 stops22h 30m
Tue 11/243:10 pm -
1 stop18h 13m
Deal found 10/4![Air Canada logo]()
$373
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:15 am -
1 stop27h 55m
Mon 12/143:10 pm -
1 stop22h 03m
Deal found 10/3![Air Canada logo]()
$380
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:17 pm -
1 stop19h 53m
Thu 11/53:20 pm -
2 stops24h 32m
Deal found 10/4![Air Canada logo]()
$383
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.
Wed 10/2811:30 pm -
1 stop10h 20m
Wed 11/49:30 am -
1 stop11h 00m
Deal found 9/30![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
Sun 12/205:35 am -
1 stop7h 20m
Deal found 10/1![Avianca logo]()
$410
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 5, 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 5, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:13 pm -
1 stop18h 54m
Thu 11/1210:03 am -
1 stop14h 08m
Deal found 10/2![Copa Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/209:50 am -
2 stops12h 15m
Sat 1/233:55 pm -
1 stop16h 39m
Deal found 10/3![Delta logo]()
$470
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:02 am -
Nonstop5h 13m
Tue 1/191:15 am -
1 stop10h 00m
Deal found 10/2![United Airlines logo]()
$558
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/58:50 pm -
2 stops17h 40m
Wed 1/203:25 pm -
2 stops14h 20m
Deal found 10/2![Southwest logo]()
$639
This Alaska Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:57 pm -
2 stops25h 34m
Thu 2/48:33 am -
2 stops28h 40m
Deal found 10/4![Alaska Airlines logo]()
$656
This Copa Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/213:13 pm -
1 stop9h 45m
Mon 3/295:20 pm -
1 stop19h 14m
Deal found 10/3![Copa Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/16:00 am -
1 stop6h 45m
Thu 2/42:00 pm -
1 stop8h 10m
Deal found 10/3![Delta logo]()
$501
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 3/247:02 am -
Nonstop5h 13m
Wed 3/311:25 pm -
1 stop8h 11m
Deal found 10/1![United Airlines logo]()
$565
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 1/157:02 am -
Nonstop5h 13m
Mon 1/181:15 am -
1 stop8h 55m
Deal found 9/30![United Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:00 am -
1 stop8h 00m
Wed 10/281:00 pm -
1 stop9h 15m
Deal found 10/2![Southwest logo]()
$643
This Alaska Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/26:57 pm -
2 stops25h 34m
Fri 2/58:33 am -
2 stops28h 40m
Deal found 10/2![Alaska Airlines logo]()
$656
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/45:30 am -
1 stop8h 40m
Wed 1/201:50 pm -
1 stop18h 53m
Deal found 10/2![Delta logo]()
$600
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 10/305:27 pm -
1 stop17h 58m
Fri 11/62:25 pm -
1 stop9h 01m
Deal found 9/30![United Airlines logo]()
$568
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/247:45 pm -
2 stops18h 30m
Wed 3/33:25 pm -
2 stops14h 20m
Deal found 10/4![Southwest logo]()
$648
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.
Sat 1/306:00 am -
1 stop6h 45m
Thu 2/42:00 pm -
1 stop8h 10m
Deal found 9/30![Delta logo]()
$608
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:25 am -
1 stop13h 14m
Wed 1/278:45 am -
2 stops12h 48m
Deal found 10/3![United Airlines logo]()
$569
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.
Wed 1/272:13 pm -
3 stops30h 18m
Sat 2/68:33 am -
2 stops28h 40m
Deal found 9/30![Alaska Airlines logo]()
$714
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop7h 10m
Mon 12/72:45 pm -
1 stop8h 20m
Deal found 10/2![Southwest logo]()
$659
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.
Sat 10/316:04 am -
1 stop8h 06m
Thu 12/32:00 pm -
1 stop8h 54m
Deal found 9/30![Delta logo]()
$608
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 2/257:02 am -
Nonstop5h 13m
Wed 3/31:25 pm -
Nonstop5h 32m
Deal found 10/1![United Airlines logo]()
$571
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 10/286:04 am -
1 stop6h 41m
Sun 11/12:00 pm -
1 stop8h 33m
Deal found 9/30![Delta logo]()
$608
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 1/219:15 am -
1 stop11h 24m
Thu 1/281:25 pm -
Nonstop5h 32m
Deal found 10/1![United Airlines logo]()
$576
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.
Wed 3/2410:05 am -
2 stops10h 35m
Wed 3/311:55 pm -
1 stop9h 25m
Deal found 10/1![Southwest logo]()
$705
This Alaska Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/56:57 pm -
2 stops25h 34m
Wed 1/208:33 am -
2 stops28h 40m
Deal found 10/2![Alaska Airlines logo]()
$780
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 12/81:02 pm -
1 stop9h 15m
Wed 12/167:00 am -
1 stop9h 16m
Deal found 9/30![Delta logo]()
$616
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:20 am -
1 stop7h 55m
Tue 11/242:10 pm -
1 stop7h 45m
Deal found 10/3![Southwest logo]()
$711
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/226:57 pm -
2 stops25h 34m
Sun 1/318:33 am -
2 stops39h 26m
Deal found 10/1![Alaska Airlines logo]()
$799
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:00 am -
1 stop6h 45m
Fri 2/57:05 am -
1 stop9h 20m
Deal found 10/2![Delta logo]()
$617
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/207:46 am -
Nonstop5h 10m
Sat 1/234:56 pm -
1 stop12h 58m
Deal found 10/2![United Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:10 am -
1 stop8h 30m
Wed 10/211:00 pm -
1 stop9h 15m
Deal found 10/4![Southwest logo]()
$720
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated October 5, 2026 and is based on user searches.
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 United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:15 pm -
1 stop13h 10m
Sat 11/71:55 pm -
Nonstop5h 33m
Deal found 10/3![United Airlines logo]()
$409
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.
Wed 10/2811:30 pm -
1 stop10h 20m
Wed 11/49:30 am -
1 stop11h 00m
Deal found 9/30![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 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 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 Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:17 pm -
1 stop19h 53m
Thu 11/53:20 pm -
2 stops24h 32m
Deal found 10/4![Air Canada logo]()
$383
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm -
2 stops17h 40m
Tue 11/173:20 pm -
1 stop23h 42m
Deal found 10/4![Air Canada logo]()
$368
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/1210:57 am -
2 stops27h 13m
Thu 11/193:20 pm -
1 stop23h 40m
Deal found 10/5![Air Canada logo]()
$370
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:15 am -
1 stop27h 55m
Mon 12/143:10 pm -
1 stop22h 03m
Deal found 10/3![Air Canada logo]()
$380
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:40 pm -
2 stops22h 30m
Tue 11/243:10 pm -
1 stop18h 13m
Deal found 10/4![Air Canada logo]()
$373
This Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:40 pm -
1 stop22h 40m
Thu 12/103:20 pm -
1 stop19h 47m
Deal found 10/4![Air Canada logo]()
$360
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 5, 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 5, 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 Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:45 pm -
1 stop22h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$167
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/13:45 pm -
1 stop22h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$172
This Air Canada deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:57 am -
2 stops27h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$177
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 Air Canada deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:05 am -
2 stops31h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Air Canada logo]()
$180
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 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 American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/59:00 am -
Nonstop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$230
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/38:50 pm -
1 stop17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$232
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 3/315:30 am -
1 stop9h 50m
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 5, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $360 (Air Canada) |
One-way from | $166 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $454 |
Good round-trip deal | $503 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 5, 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
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Wed 3/31
5:30 am-2:20 pm
1 stop9h 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
Mon 1/4
5:30 am-12:45 pm
1 stop7h 15m
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
Tue 3/30
7:40 pm-12:30 pm
1 stop17h 50m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 10/20
9:40 am-7:40 pm
2 stops11h 00m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 10/25
9:55 am-7:40 pm
2 stops10h 45m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 3/23
1:29 pm-11:59 pm
1 stop11h 30m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$245
ChicagoLiberia
ORD Chicago O'Hare Intl - LIR Liberia
ORDLIR
Chicago O'Hare Intl
Mon 3/22
9:20 pm-10:44 am
1 stop14h 24m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$265
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 3/18
9:10 am-7:40 pm
2 stops11h 30m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$275
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Mon 3/22
9:50 pm-2:00 pm
2 stops17h 10m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$308
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-LIR
ORD-SJO
MDW-LIR
MDW-SJO
ORD-LIO
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-LIR
ORD-SJO
MDW-LIR
MDW-SJO
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 $520). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $747). 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 5, 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 5, 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.
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Comfort
8.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
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
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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 5, 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$584 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$303 | Average$534 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$324 | Average$578 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$332 | Average$623 | 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$665 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$825 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$395 | Average$658 | FlexibilityNo cancel fee | On-time63% |