$151+ Cheap flights from Chicago (CHI) to Costa Rica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Sep 5 — Sep 121
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 August 6, 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 August 6, 2026.
This Air Canada deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 pm -
1 stop21h 40m
Mon 11/23:10 pm -
1 stop18h 13m
Deal found 8/6![Air Canada logo]()
$388
This Air Canada deal was found by Cheapflights users on 8/3. 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 10/248:40 pm -
1 stop17h 30m
Sat 10/312:20 pm -
1 stop24h 32m
Deal found 8/3![Air Canada logo]()
$411
This Air Canada deal was found by Cheapflights users on 8/5. 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 10/245:35 pm -
1 stop20h 35m
Mon 11/23:10 pm -
1 stop18h 13m
Deal found 8/5![Air Canada logo]()
$416
This Air Canada deal was found by Cheapflights users on 8/4. 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 11/23:45 pm -
1 stop22h 35m
Thu 11/53:20 pm -
1 stop19h 47m
Deal found 8/4![Air Canada logo]()
$420
This Air Canada deal was found by Cheapflights users on 8/5. 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.
Mon 10/269:05 pm -
1 stop17h 05m
Tue 11/33:20 pm -
1 stop23h 32m
Deal found 8/5![Air Canada logo]()
$425
This Copa Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:01 am -
1 stop24h 09m
Mon 10/268:44 am -
1 stop15h 21m
Deal found 8/4![Copa Airlines logo]()
$481
This Volaris deal was found by Cheapflights users on 8/5. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:49 pm -
1 stop11h 10m
Tue 10/134:15 pm -
1 stop18h 54m
Deal found 8/5![Multiple Airlines logo]()
$488
This Volaris deal was found by Cheapflights users on 8/5. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:24 am -
1 stop22h 35m
Thu 12/104:15 pm -
1 stop18h 53m
Deal found 8/5![Multiple Airlines logo]()
$491
This Copa Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 11/72:13 pm -
1 stop16h 49m
Fri 11/133:59 am -
1 stop8h 47m
Deal found 8/6![Copa Airlines logo]()
$496
This Viva deal was found by Cheapflights users on 8/4. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2712:35 am -
1 stop24h 50m
Mon 1/42:25 am -
1 stop20h 35m
Deal found 8/4![Viva logo]()
$498
This Copa Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 11/262:13 pm -
1 stop16h 49m
Sat 12/262:17 pm -
1 stop9h 54m
Deal found 8/2![Copa Airlines logo]()
$500
This Sembo deal was found by Cheapflights users on 8/3. 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 Sembo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:21 pm -
1 stop18h 43m
Wed 8/195:55 pm -
1 stop30h 07m
Deal found 8/3![Copa Airlines logo]()
$501
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 August 6, 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 August 6, 2026.
This Volaris deal was found by Cheapflights users on 8/5. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:49 pm -
1 stop11h 10m
Tue 10/134:15 pm -
1 stop18h 54m
Deal found 8/5![Multiple Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 11/125:15 am -
1 stop7h 05m
Sat 11/212:45 pm -
1 stop9h 40m
Deal found 8/3![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 11/146:00 am -
1 stop7h 05m
Sat 11/217:00 am -
1 stop9h 14m
Deal found 8/6![Delta logo]()
$552
This United Airlines deal was found by Cheapflights users on 8/3. 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 1/307:54 am -
Nonstop5h 06m
Thu 2/42:01 pm -
Nonstop5h 19m
Deal found 8/3![United Airlines logo]()
$752
This Alaska Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 1/305:55 pm -
2 stops24h 30m
Thu 2/410:00 am -
3 stops28h 12m
Deal found 8/2![Alaska Airlines logo]()
$841
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:15 am -
1 stop7h 05m
Fri 11/132:10 pm -
1 stop10h 55m
Deal found 8/1![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 12/31:00 pm -
1 stop9h 15m
Fri 12/117:00 am -
2 stops11h 04m
Deal found 8/6![Delta logo]()
$557
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:20 pm -
2 stops16h 25m
Mon 11/22:45 pm -
2 stops19h 45m
Deal found 8/5![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 8/4. 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 10/219:40 am -
2 stops11h 00m
Tue 10/279:00 am -
2 stops12h 10m
Deal found 8/4![Southwest logo]()
$526
This Delta deal was found by Cheapflights users on 8/1. 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 9/245:30 am -
1 stop7h 24m
Tue 10/61:25 pm -
1 stop9h 27m
Deal found 8/1![Delta logo]()
$590
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:25 pm -
2 stops17h 20m
Thu 11/121:20 pm -
2 stops11h 45m
Deal found 8/1![Southwest logo]()
$526
This Delta deal was found by Cheapflights users on 8/1. 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 9/235:10 pm -
2 stops19h 44m
Mon 10/51:19 pm -
2 stops22h 40m
Deal found 8/1![Delta logo]()
$595
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:05 am -
1 stop9h 40m
Tue 9/291:40 pm -
1 stop8h 35m
Deal found 8/5![Southwest logo]()
$534
This Delta deal was found by Cheapflights users on 8/2. 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.
Wed 1/275:30 am -
1 stop7h 15m
Sun 1/317:05 am -
2 stops11h 35m
Deal found 8/2![Delta logo]()
$595
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sun 1/37:17 am -
Nonstop5h 18m
Sat 1/92:05 pm -
Nonstop5h 30m
Deal found 8/1![United Airlines logo]()
$808
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/1610:10 am -
2 stops9h 35m
Wed 9/239:00 am -
1 stop9h 15m
Deal found 8/2![Southwest logo]()
$539
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 12/48:04 am -
1 stop14h 11m
Wed 12/97:00 am -
2 stops11h 33m
Deal found 8/1![Delta logo]()
$595
This United Airlines deal was found by Cheapflights users on 8/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:52 pm -
1 stop17h 29m
Wed 9/97:55 am -
1 stop9h 35m
Deal found 8/5![United Airlines logo]()
$810
This Southwest deal was found by Cheapflights users on 8/1. 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.
Mon 9/145:00 am -
1 stop8h 45m
Mon 9/211:40 pm -
1 stop7h 40m
Deal found 8/1![Southwest logo]()
$539
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 12/317:17 am -
Nonstop5h 18m
Thu 1/72:05 pm -
Nonstop5h 30m
Deal found 8/2![United Airlines logo]()
$833
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:18 pm -
3 stops30h 34m
Sat 9/268:40 am -
2 stops20h 40m
Deal found 8/5![Alaska Airlines logo]()
$1,044
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
1 stop8h 35m
Fri 10/169:00 am -
2 stops10h 10m
Deal found 8/5![Southwest logo]()
$545
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sun 11/296:55 am -
1 stop11h 42m
Sat 12/52:01 pm -
Nonstop5h 19m
Deal found 8/2![United Airlines logo]()
$850
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:05 am -
1 stop6h 55m
Sat 9/191:25 pm -
1 stop8h 19m
Deal found 8/5![Delta logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 8/2. 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 10/132:21 pm -
3 stops30h 30m
Sun 10/189:16 am -
2 stops19h 24m
Deal found 8/2![Alaska Airlines logo]()
$1,202
This United Airlines deal was found by Cheapflights users on 8/3. 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 12/299:25 am -
Nonstop5h 15m
Tue 1/52:06 pm -
Nonstop5h 23m
Deal found 8/3![United Airlines logo]()
$909
This Delta deal was found by Cheapflights users on 8/3. 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.
Tue 12/295:30 am -
1 stop7h 15m
Thu 1/147:05 am -
2 stops13h 32m
Deal found 8/3![Delta logo]()
$761
This Alaska Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:52 pm -
2 stops21h 12m
Sat 12/511:22 am -
3 stops25h 47m
Deal found 8/3![Alaska Airlines logo]()
$1,204
This Delta deal was found by Cheapflights users on 8/2. 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.
Thu 12/108:29 am -
2 stops13h 46m
Mon 12/142:30 pm -
2 stops17h 16m
Deal found 8/2![Delta logo]()
$769
This United Airlines deal was found by Cheapflights users on 8/1. 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 1/29:25 am -
Nonstop5h 15m
Wed 1/62:06 pm -
Nonstop5h 23m
Deal found 8/1![United Airlines logo]()
$937
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated August 6, 2026 and is based on user searches.
This Sembo deal was found by Cheapflights users on 8/3. 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 Sembo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/63:21 pm -
1 stop18h 43m
Wed 8/195:55 pm -
1 stop30h 07m
Deal found 8/3![Copa Airlines logo]()
$501
This Avianca deal was found by Cheapflights users on 8/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/73:40 pm -
1 stop8h 35m
Sun 8/95:45 am -
1 stop7h 20m
Deal found 8/3![Avianca logo]()
$523
This Avianca deal was found by Cheapflights users on 8/1. 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.
Sun 8/1611:20 pm -
1 stop10h 30m
Wed 8/195:45 am -
1 stop7h 20m
Deal found 8/1![Avianca logo]()
$521
This Avianca deal was found by Cheapflights users on 8/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/173:40 pm -
1 stop17h 50m
Thu 8/205:05 am -
1 stop9h 50m
Deal found 8/3![Avianca logo]()
$522
This Avianca deal was found by Cheapflights users on 8/1. 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.
Fri 8/2111:20 pm -
1 stop10h 30m
Fri 8/289:25 am -
1 stop10h 55m
Deal found 8/1![Avianca logo]()
$518
This Avianca deal was found by Cheapflights users on 8/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:15 pm -
1 stop7h 25m
Mon 8/247:45 pm -
1 stop19h 10m
Deal found 8/3![Avianca logo]()
$520
This Copa Airlines deal was found by Cheapflights users on 8/1. 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.
Mon 8/243:21 pm -
1 stop16h 49m
Fri 8/2810:03 am -
1 stop13h 59m
Deal found 8/1![Copa Airlines logo]()
$506
This KAYAK deal was found by Cheapflights users on 8/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:00 am -
1 stop7h 01m
Thu 9/32:06 pm -
1 stop8h 38m
Deal found 8/4![JetBlue logo]()
$499
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop6h 57m
Thu 9/241:05 pm -
1 stop9h 03m
Deal found 8/4![JetBlue logo]()
$500
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 9/187:55 pm -
2 stops17h 50m
Sun 9/202:10 pm -
2 stops16h 20m
Deal found 8/2![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 9/2410:05 am -
1 stop9h 40m
Mon 9/281:40 pm -
1 stop7h 40m
Deal found 8/3![Southwest logo]()
$522
This KAYAK deal was found by Cheapflights users on 8/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am -
1 stop6h 57m
Sat 10/31:05 pm -
1 stop9h 03m
Deal found 8/5![JetBlue logo]()
$478
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 August 6, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Viva deal was found by Cheapflights users on 8/5. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/3112:35 am -
1 stop24h 50m
Deal found 8/5![Viva logo]()
$151
This Viva deal was found by Cheapflights users on 8/4. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:35 am -
1 stop24h 50m
Deal found 8/4![Viva logo]()
$157
This Viva deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:30 am -
1 stop24h 50m
Deal found 8/6![Viva logo]()
$162
This Viva deal was found by Cheapflights users on 8/5. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2112:30 am -
1 stop24h 50m
Deal found 8/5![Viva logo]()
$166
This Viva deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 1/2812:30 am -
1 stop24h 50m
Deal found 8/6![Viva logo]()
$182
This Viva deal was found by Cheapflights users on 8/4. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/112:35 am -
1 stop24h 50m
Deal found 8/4![Viva logo]()
$185
This Viva deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/3112:30 am -
1 stop24h 50m
Deal found 8/1![Viva logo]()
$191
This Air Canada deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/23:45 pm -
1 stop22h 35m
Deal found 8/3![Air Canada logo]()
$204
This Volaris deal was found by Cheapflights users on 8/3. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/301:24 am -
1 stop22h 35m
Deal found 8/3![Multiple Airlines logo]()
$205
This Viva deal was found by Cheapflights users on 8/5. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:20 pm -
1 stop20h 55m
Deal found 8/5![Viva logo]()
$208
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop6h 57m
Deal found 8/6![JetBlue logo]()
$209
This Air Canada deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:45 pm -
2 stops22h 25m
Deal found 8/4![Air Canada logo]()
$212
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $411 (Air Canada) |
One-way from | $151 (Viva) |
Popular in | December |
Cheapest in | September |
Average price | $601 |
Good round-trip deal | $627 or less |
Good one-way deal | $387 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Costa Rica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Thu 10/8
1:49 pm-11:59 pm
1 stop11h 10m
San José Juan Santamaria Intl
Tue 10/13
4:15 pm-12:09 pm
1 stop18h 54m
$488
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 11/12
5:15 am-12:20 pm
1 stop7h 05m
San José Juan Santamaria Intl
Sat 11/21
2:45 pm-12:25 am
1 stop9h 40m
$522
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Fri 11/6
5:15 am-12:20 pm
1 stop7h 05m
San José Juan Santamaria Intl
Fri 11/13
2:10 pm-1:05 am
1 stop10h 55m
$522
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Fri 10/30
9:20 pm-12:45 pm
2 stops16h 25m
Liberia
Mon 11/2
2:45 pm-10:30 am
2 stops19h 45m
$526
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 10/21
9:40 am-7:40 pm
2 stops11h 00m
San José Juan Santamaria Intl
Tue 10/27
9:00 am-10:10 pm
2 stops12h 10m
$526
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Fri 11/6
8:25 pm-1:45 pm
2 stops17h 20m
San José Juan Santamaria Intl
Thu 11/12
1:20 pm-1:05 am
2 stops11h 45m
$526
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 9/28
10:05 am-6:45 pm
1 stop9h 40m
San José Juan Santamaria Intl
Tue 9/29
1:40 pm-11:15 pm
1 stop8h 35m
$534
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 9/16
10:10 am-6:45 pm
2 stops9h 35m
San José Juan Santamaria Intl
Wed 9/23
9:00 am-7:15 pm
1 stop9h 15m
$539
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 9/14
5:00 am-12:45 pm
1 stop8h 45m
San José Juan Santamaria Intl
Mon 9/21
1:40 pm-10:20 pm
1 stop7h 40m
$539
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 10/12
5:00 am-12:35 pm
1 stop8h 35m
San José Juan Santamaria Intl
Fri 10/16
9:00 am-8:10 pm
2 stops10h 10m
$545
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, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $454). Flying from Chicago to Costa Rica in December is currently the most expensive (average of $720). 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 August 6, 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 163 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 5 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 August 6, 2026.
Read reviews from past customers who have flown Southwest,Delta, andCopa Airlines from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Costa Rica
Discover the top 10 airlines that operate flights from Chicago to Costa Rica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$672 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$151 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$221 | Average$596 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$303 | Average$490 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$309 | Average$584 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$312 | Average$616 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$337 | Average$622 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$1,007 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$386 | Average$652 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$394 | Average$649 | FlexibilityNo cancel fee | On-time63% |