$146+ Cheap flights from Costa Rica to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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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 Costa Rica to ChicagoExplore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.
Explore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/51:25 pm -
1 stop9h 02m
Wed 10/149:38 pm -
1 stop15h 43m
Deal found 8/7![United Airlines logo]()
$375
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/910:03 am -
1 stop26h 56m
Wed 10/143:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$379
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.
Mon 10/263:58 am -
1 stop20h 07m
Fri 11/62:13 pm -
1 stop20h 46m
Deal found 8/4![Copa Airlines logo]()
$381
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.
Wed 10/282:10 pm -
1 stop18h 13m
Wed 11/43:45 pm -
1 stop22h 35m
Deal found 8/4![Air Canada logo]()
$385
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/712:44 pm -
1 stop9h 37m
Tue 10/139:38 pm -
1 stop22h 59m
Deal found 8/7![United Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/21:25 pm -
1 stop24h 25m
Tue 10/139:38 pm -
1 stop22h 59m
Deal found 8/7![United Airlines logo]()
$392
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.
Fri 9/2510:03 am -
1 stop26h 56m
Thu 10/18:01 am -
1 stop24h 09m
Deal found 8/4![Copa Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/222:25 pm -
1 stop10h 12m
Sat 1/29:36 pm -
1 stop24h 56m
Deal found 8/7![United Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/291:15 am -
1 stop8h 52m
Fri 1/87:02 am -
Nonstop5h 13m
Deal found 8/8![United Airlines logo]()
$406
This deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 am -
1 stop11h 10m
Thu 9/248:45 am -
1 stop11h 52m
Deal found 8/7![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:25 pm -
1 stop9h 58m
Tue 10/136:25 am -
1 stop14h 12m
Deal found 8/8![United Airlines logo]()
$410
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:08 am -
1 stop8h 51m
Sun 10/188:01 am -
1 stop26h 03m
Deal found 8/7![Copa Airlines logo]()
$413
Best flights from Costa Rica to ChicagoDiscover carefully curated flight deals from Costa Rica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
Discover carefully curated flight deals from Costa Rica to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:15 am -
1 stop8h 10m
Mon 1/259:25 am -
1 stop8h 51m
Deal found 8/8![United Airlines logo]()
$375
This Copa Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/192:18 pm -
1 stop9h 53m
Wed 11/252:13 pm -
1 stop22h 07m
Deal found 8/8![Copa Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/207:00 am -
2 stops13h 24m
Fri 1/17:05 am -
2 stops15h 10m
Deal found 8/8![Delta logo]()
$499
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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.
Wed 10/212:05 pm -
1 stop8h 39m
Sat 10/247:00 am -
1 stop6h 55m
Deal found 8/8![JetBlue logo]()
$504
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:15 pm -
1 stop18h 54m
Sun 8/306:21 am -
1 stop18h 38m
Deal found 8/4![Multiple Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/309:00 am -
1 stop10h 20m
Sat 11/75:00 am -
1 stop8h 45m
Deal found 8/8![Southwest logo]()
$542
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 12/222:37 pm -
Nonstop5h 25m
Wed 12/308:15 am -
Nonstop5h 22m
Deal found 8/7![American Airlines logo]()
$621
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.
Tue 12/223:20 pm -
1 stop19h 47m
Wed 12/303:45 pm -
1 stop22h 35m
Deal found 8/5![Air Canada logo]()
$628
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/263:58 am -
1 stop20h 07m
Fri 11/62:13 pm -
1 stop20h 46m
Deal found 8/7![Copa Airlines logo]()
$398
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.
Thu 10/295:55 pm -
1 stop18h 51m
Mon 11/92:13 pm -
1 stop20h 46m
Deal found 8/6![Copa Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/202:15 pm -
1 stop9h 07m
Fri 1/16:50 am -
1 stop11h 26m
Deal found 8/8![United Airlines logo]()
$451
This Copa Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/1310:03 am -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop18h 44m
Deal found 8/8![Copa Airlines logo]()
$413
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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.
Wed 10/212:05 pm -
1 stop8h 39m
Sun 10/257:00 am -
1 stop7h 00m
Deal found 8/8![JetBlue logo]()
$504
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:40 pm -
1 stop7h 40m
Thu 9/2410:05 am -
2 stops9h 40m
Deal found 8/6![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:00 am -
1 stop15h 56m
Wed 12/21:00 pm -
1 stop9h 15m
Deal found 8/7![Delta logo]()
$550
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/72:05 pm -
1 stop7h 35m
Wed 11/115:20 am -
1 stop7h 55m
Deal found 8/8![Southwest logo]()
$542
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.
Tue 10/2010:03 am -
1 stop13h 54m
Thu 10/298:35 am -
1 stop24h 44m
Deal found 8/4![Copa Airlines logo]()
$485
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.
Thu 9/241:40 pm -
1 stop7h 40m
Sun 9/277:10 am -
2 stops12h 30m
Deal found 8/4![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
1 stop15h 56m
Wed 11/251:22 pm -
2 stops8h 53m
Deal found 8/8![Delta logo]()
$644
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:47 pm -
1 stop8h 46m
Sat 10/36:00 am -
1 stop8h 47m
Deal found 8/4![American Airlines logo]()
$732
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 12/207:00 am -
1 stop15h 10m
Fri 1/19:30 am -
2 stops12h 45m
Deal found 8/7![Delta logo]()
$651
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/99:00 am -
1 stop10h 20m
Tue 10/139:40 am -
2 stops11h 00m
Deal found 8/8![Southwest logo]()
$597
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:20 pm -
1 stop10h 39m
Sun 9/65:30 am -
1 stop7h 40m
Deal found 8/9![United Airlines logo]()
$783
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/257:00 am -
1 stop15h 10m
Sat 1/29:30 am -
2 stops12h 45m
Deal found 8/8![Delta logo]()
$651
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 12/217:00 am -
1 stop9h 25m
Fri 1/16:00 am -
1 stop16h 15m
Deal found 8/7![Delta logo]()
$651
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.
Fri 11/201:20 pm -
2 stops10h 45m
Wed 11/259:05 pm -
2 stops17h 20m
Deal found 8/4![Southwest logo]()
$656
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:25 pm -
1 stop9h 34m
Mon 9/285:30 am -
1 stop7h 30m
Deal found 8/4![Delta logo]()
$670
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/211:20 pm -
1 stop9h 07m
Sat 10/247:49 am -
Nonstop5h 04m
Deal found 8/7![United Airlines logo]()
$957
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:19 pm -
1 stop8h 25m
Mon 9/286:05 am -
1 stop6h 49m
Deal found 8/4![Delta logo]()
$683
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/271:25 pm -
2 stops17h 31m
Sun 10/117:30 pm -
2 stops17h 05m
Deal found 8/8![Delta logo]()
$692
Last-minute flights from Costa Rica to ChicagoDiscover last-minute flight deals from Costa Rica to Chicago. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Chicago. Data last updated August 9, 2026 and is based on user searches.
This Ovago deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:25 pm -
1 stop18h 44m
Mon 8/315:30 am -
1 stop7h 51m
Deal found 8/7![Multiple Airlines logo]()
$434
This Faresmojo 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:00 am -
1 stop9h 15m
Sun 9/208:05 am -
1 stop11h 35m
Deal found 8/4![JetBlue logo]()
$488
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/125:55 pm -
1 stop19h 04m
Sun 9/203:20 pm -
1 stop16h 50m
Deal found 8/7![Copa Airlines logo]()
$445
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:55 pm -
1 stop19h 04m
Sat 9/198:01 am -
1 stop26h 03m
Deal found 8/5![Copa Airlines logo]()
$463
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/1310:03 am -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$413
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:03 am -
1 stop26h 56m
Tue 9/228:01 am -
1 stop24h 09m
Deal found 8/5![Copa Airlines logo]()
$379
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 9/1710:03 am -
1 stop13h 59m
Thu 10/18:01 am -
1 stop26h 03m
Deal found 8/4![Copa Airlines logo]()
$381
This deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 am -
1 stop11h 10m
Thu 9/248:45 am -
1 stop11h 52m
Deal found 8/7![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/221:19 pm -
1 stop8h 25m
Sat 9/266:05 am -
1 stop6h 49m
Deal found 8/8![Delta logo]()
$499
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/231:25 pm -
1 stop18h 44m
Sun 9/276:25 am -
1 stop14h 12m
Deal found 8/8![United Airlines logo]()
$401
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.
Thu 9/241:05 pm -
1 stop9h 03m
Mon 9/286:00 am -
1 stop6h 57m
Deal found 8/4![JetBlue logo]()
$495
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.
Fri 9/2510:03 am -
1 stop26h 56m
Thu 10/18:01 am -
1 stop24h 09m
Deal found 8/4![Copa Airlines logo]()
$397
One-way flights from Costa Rica to ChicagoSearch for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
Search for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Viva deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/32:25 am -
1 stop20h 35m
Deal found 8/8![Viva logo]()
$146
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 9/241:15 pm -
1 stop24h 37m
Deal found 8/6![Viva logo]()
$164
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.
Thu 11/192:25 am -
1 stop20h 30m
Deal found 8/4![Viva logo]()
$194
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:10 pm -
1 stop26h 33m
Deal found 8/7![Air Canada logo]()
$198
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:20 pm -
1 stop28h 32m
Deal found 8/5![Air Canada logo]()
$211
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 12/102:25 am -
1 stop20h 35m
Deal found 8/5![Viva logo]()
$214
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:10 pm -
1 stop24h 28m
Deal found 8/5![Air Canada logo]()
$216
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.
Tue 11/33:20 pm -
2 stops29h 01m
Deal found 8/5![Air Canada logo]()
$217
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:05 pm -
1 stop9h 03m
Deal found 8/5![JetBlue logo]()
$220
This Volaris deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:15 pm -
1 stop18h 54m
Deal found 8/7![Multiple Airlines logo]()
$222
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:50 pm -
1 stop10h 38m
Deal found 8/5![JetBlue logo]()
$226
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/83:10 pm -
1 stop24h 28m
Deal found 8/5![Air Canada logo]()
$227
Find flight deals from Costa Rica to Chicago
Keep the following information in mind while searching for Costa Rica to Chicago flight deals. Data was last updated August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $375 (United Airlines) |
One-way from | $146 (Viva) |
Popular in | July |
Cheapest in | January |
Average price | $499 |
Good round-trip deal | $433 or less |
Good one-way deal | $264 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Costa Rica to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Wed 1/13
1:15 am-9:25 am
1 stop8h 10m
Chicago O'Hare Intl
Mon 1/25
9:25 am-6:16 pm
1 stop8h 51m
$375
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 11/19
2:18 pm-12:11 am
1 stop9h 53m
Chicago O'Hare Intl
Wed 11/25
2:13 pm-12:20 pm
1 stop22h 07m
$398
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Mon 10/26
3:58 am-1:05 am
1 stop20h 07m
Chicago O'Hare Intl
Fri 11/6
2:13 pm-10:59 am
1 stop20h 46m
$398
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 10/29
5:55 pm-1:46 pm
1 stop18h 51m
Chicago O'Hare Intl
Mon 11/9
2:13 pm-10:59 am
1 stop20h 46m
$398
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 9/13
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sat 9/19
3:20 pm-9:04 am
1 stop18h 44m
$413
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 12/20
2:15 pm-11:22 pm
1 stop9h 07m
Chicago O'Hare Intl
Fri 1/1
6:50 am-6:16 pm
1 stop11h 26m
$451
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Tue 10/20
10:03 am-12:57 am
1 stop13h 54m
Chicago O'Hare Intl
Thu 10/29
8:35 am-8:19 am
1 stop24h 44m
$485
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 12/20
7:00 am-8:24 pm
2 stops13h 24m
Chicago O'Hare Intl
Fri 1/1
7:05 am-10:15 pm
2 stops15h 10m
$499
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Wed 10/21
2:05 pm-11:44 pm
1 stop8h 39m
Chicago O'Hare Intl
Sat 10/24
7:00 am-12:55 pm
1 stop6h 55m
$504
LiberiaChicago
LIR Liberia - ORD Chicago O'Hare Intl
LIRORD
Liberia
Wed 10/21
2:05 pm-11:44 pm
1 stop8h 39m
Chicago O'Hare Intl
Sun 10/25
7:00 am-1:00 pm
1 stop7h 00m
$504
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Costa Rica to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Costa Rica with our price prediction graph.
SJO-ORD
SJO-MDW
LIR-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Costa Rica to Chicago
CR0-CHI
SJO-ORD
SJO-MDW
LIR-ORD
What is the cheapest month to book a flight from Costa Rica to Chicago?
Currently, January is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $388). Flying from Costa Rica to Chicago in July is currently the most expensive (average of $639). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CR to CHI?
Find hourly flight availability from Costa Rica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 9, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Costa Rica to Chicago as you normally would.
How often are flights from Costa Rica to Chicago delayed?
About 9% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 193 minutes.
What is the most punctual flight time for Costa Rica to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Costa Rica to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
How far ahead should I book a flight from Costa Rica to Chicago?
Booking 29 days in advance of your planned departure date is, on average, the best time to get cheap flights from Costa Rica to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 9, 2026.
Read reviews from past customers who have flown Southwest,Copa Airlines, andUnited Airlines from Costa Rica to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Costa Rica to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Costa Rica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 9, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Costa Rica to Chicago by cabin class
Find flights from Costa Rica to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Costa Rica and Chicago flights
Browse other Costa Rica and Chicago flight options. Last updated on August 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Costa Rica to Chicago
Discover the top 5 airlines that operate flights from Costa Rica to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$493 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$518 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$491 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$636 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$390 | Average$589 | FlexibilityNo cancel fee | On-time63% |