$128+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Apr 6 — Apr 131
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Costa Rica
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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 March 7, 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 March 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Wed 3/1112:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$323
This Expedia deal was found by Cheapflights users on 3/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
ORD
- SJO
1 stop7h 57m
Multiple Airlines
Thu 4/1612:38 pm
SJO
- ORD
1 stop10h 46m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Thu 3/1212:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$325
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Tue 4/2112:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$326
This Super.com deal was found by Cheapflights users on 3/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Thu 4/1612:38 pm
SJO
- ORD
1 stop10h 46m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Sat 3/71:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- SJO
1 stop19h 21m
Multiple Airlines
Wed 4/153:10 pm
SJO
- ORD
3 stops31h 49m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$333
This Gotogate deal was found by Cheapflights users on 3/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Wed 3/114:06 pm
SJO
- ORD
1 stop18h 13m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$334
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:34 pm
ORD
- SJO
1 stop18h 41m
Spirit Airlines
Thu 4/2312:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$335
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$337
This FlightHub deal was found by Cheapflights users on 3/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:41 pm
MDW
- SJO
1 stop14h 04m
Frontier
Mon 6/110:00 am
SJO
- MDW
2 stops20h 00m
Frontier
Deal found 3/6![Frontier logo]()
$377
This Southwest deal was found by Cheapflights users on 3/3. 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.
Mon 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$395
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 March 7, 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 March 7, 2026.
This Copa Airlines deal was found by Cheapflights users on 3/3. 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.
Wed 4/153:05 pm
ORD
- SJO
1 stop17h 03m
Copa Airlines
Wed 4/225:46 am
SJO
- ORD
1 stop18h 27m
Copa Airlines
Deal found 3/3![Copa Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 3/2. 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 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Fri 5/19:00 am
SJO
- MDW
2 stops12h 45m
Southwest
Deal found 3/2![Southwest logo]()
$440
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 5/164:00 pm
ORD
- SJO
1 stop14h 30m
United Airlines
Sun 5/2411:13 am
SJO
- ORD
1 stop9h 23m
United Airlines
Deal found 3/2![United Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 3/4. 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.
Tue 5/126:00 am
ORD
- LIR
1 stop7h 00m
Delta
Wed 5/131:25 pm
LIR
- ORD
1 stop9h 34m
Delta
Deal found 3/4![Delta logo]()
$488
This Alaska Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 4/186:00 am
ORD
- LIR
3 stops25h 20m
Alaska Airlines
Sat 4/255:09 pm
LIR
- ORD
2 stops29h 50m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$853
This Copa Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 4/173:05 pm
ORD
- SJO
1 stop19h 00m
Copa Airlines
Mon 4/276:19 pm
SJO
- ORD
1 stop18h 31m
Copa Airlines
Deal found 3/2![Copa Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 3/3. 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.
Fri 5/295:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Thu 6/41:40 pm
SJO
- MDW
1 stop8h 20m
Southwest
Deal found 3/3![Southwest logo]()
$464
This Copa Airlines deal was found by Cheapflights users on 3/3. 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.
Wed 4/83:05 pm
ORD
- SJO
1 stop19h 00m
Copa Airlines
Wed 4/154:09 am
SJO
- ORD
1 stop8h 41m
Copa Airlines
Deal found 3/3![Copa Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Mon 5/255:30 am
ORD
- SJO
1 stop7h 51m
United Airlines
Fri 5/2912:30 am
SJO
- ORD
1 stop8h 50m
United Airlines
Deal found 3/5![United Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:55 am
MDW
- LIR
1 stop7h 20m
Southwest
Wed 4/152:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/7![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 3/4. 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.
Mon 5/115:19 pm
ORD
- LIR
2 stops19h 41m
Delta
Sat 5/162:40 pm
LIR
- ORD
2 stops18h 47m
Delta
Deal found 3/4![Delta logo]()
$513
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Mon 3/98:53 am
ORD
- SJO
1 stop13h 39m
United Airlines
Wed 3/111:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Deal found 3/5![United Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 3/117:10 am
ORD
- SJO
2 stops15h 05m
Delta
Mon 3/161:20 pm
SJO
- ORD
1 stop9h 34m
Delta
Deal found 3/6![Delta logo]()
$533
This Southwest deal was found by Cheapflights users on 3/3. 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.
Wed 4/812:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Wed 4/159:00 am
SJO
- MDW
2 stops9h 45m
Southwest
Deal found 3/3![Southwest logo]()
$488
This United Airlines deal was found by Cheapflights users on 3/2. 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 4/235:48 am
ORD
- LIR
1 stop9h 37m
United Airlines
Sun 4/263:27 pm
LIR
- ORD
1 stop8h 59m
United Airlines
Deal found 3/2![United Airlines logo]()
$528
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 3/98:15 am
MDW
- SJO
1 stop12h 25m
Southwest
Wed 3/118:45 am
SJO
- MDW
1 stop9h 35m
Southwest
Deal found 3/6![Southwest logo]()
$519
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Thu 5/145:30 am
ORD
- LIR
1 stop9h 55m
United Airlines
Sun 5/173:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Deal found 3/5![United Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 3/3. 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 3/3012:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Tue 4/77:00 am
SJO
- MDW
1 stop9h 22m
Delta
Deal found 3/3![Delta logo]()
$601
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Thu 4/1610:45 pm
ORD
- LIR
1 stop16h 40m
United Airlines
Mon 4/203:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Deal found 3/5![United Airlines logo]()
$528
This Southwest deal was found by Cheapflights users on 3/4. 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.
Mon 5/186:55 am
MDW
- LIR
1 stop7h 20m
Southwest
Tue 5/262:10 pm
LIR
- MDW
2 stops14h 15m
Southwest
Deal found 3/4![Southwest logo]()
$533
This Delta deal was found by Cheapflights users on 3/2. 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 3/1112:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Sat 3/147:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 3/2![Delta logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 3/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:05 pm
ORD
- LIR
2 stops22h 24m
Alaska Airlines
Mon 8/39:00 am
LIR
- ORD
2 stops19h 02m
Alaska Airlines
Deal found 3/7![Alaska Airlines logo]()
$859
This United Airlines deal was found by Cheapflights users on 3/2. 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 6/35:30 am
ORD
- SJO
1 stop7h 51m
United Airlines
Sun 6/76:00 am
SJO
- ORD
1 stop16h 16m
United Airlines
Deal found 3/2![United Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 3/2. 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 5/16:00 am
MDW
- SJO
1 stop6h 56m
Delta
Wed 5/61:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Deal found 3/2![Delta logo]()
$663
This Alaska Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 6/69:00 am
ORD
- LIR
3 stops22h 20m
Alaska Airlines
Sun 6/149:00 am
LIR
- ORD
3 stops19h 02m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$887
This Southwest deal was found by Cheapflights users on 3/5. 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.
Thu 5/147:20 pm
ORD
- LIR
2 stops18h 55m
Southwest
Sun 5/172:05 pm
LIR
- ORD
2 stops18h 40m
Southwest
Deal found 3/5![Southwest logo]()
$633
This United Airlines deal was found by Cheapflights users on 3/3. 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 5/25:30 am
ORD
- SJO
1 stop7h 51m
United Airlines
Sat 5/91:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Deal found 3/3![United Airlines logo]()
$582
This Delta deal was found by Cheapflights users on 3/3. 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.
Sat 4/256:00 am
MDW
- LIR
1 stop7h 00m
Delta
Sat 5/21:25 pm
LIR
- MDW
1 stop8h 03m
Delta
Deal found 3/3![Delta logo]()
$682
This Southwest deal was found by Cheapflights users on 3/6. 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.
Fri 5/297:30 am
MDW
- SJO
2 stops12h 30m
Southwest
Mon 6/19:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 3/6![Southwest logo]()
$635
This United Airlines deal was found by Cheapflights users on 3/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:10 pm
ORD
- SJO
1 stop17h 11m
United Airlines
Sat 5/91:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Deal found 3/4![United Airlines logo]()
$582
Last-minute flights from Chicago to Costa RicaDiscover last-minute flight deals from Chicago to Costa Rica. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Costa Rica. Data last updated March 7, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/58:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Wed 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$338
This Gotogate deal was found by Cheapflights users on 3/5. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:16 pm
ORD
- SJO
1 stop16h 06m
Multiple Airlines
Wed 3/114:06 pm
SJO
- ORD
1 stop18h 13m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$334
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$337
This CheapOair deal was found by Cheapflights users on 3/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Thu 4/3012:38 pm
SJO
- ORD
1 stop10h 46m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- SJO
1 stop19h 21m
Multiple Airlines
Wed 4/153:10 pm
SJO
- ORD
3 stops31h 49m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$333
This Expedia deal was found by Cheapflights users on 3/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
ORD
- SJO
1 stop7h 57m
Multiple Airlines
Thu 4/1612:38 pm
SJO
- ORD
1 stop10h 46m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$324
This Super.com deal was found by Cheapflights users on 3/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Thu 4/1612:38 pm
SJO
- ORD
1 stop10h 46m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:45 pm
ORD
- SJO
1 stop22h 57m
Multiple Airlines
Mon 4/133:10 pm
SJO
- ORD
3 stops17h 40m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 3/3. 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.
Mon 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$395
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:34 pm
ORD
- SJO
1 stop18h 41m
Spirit Airlines
Thu 4/2312:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$335
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:05 am
ORD
- SJO
1 stop7h 10m
Spirit Airlines
Tue 4/2112:20 pm
SJO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/2![Spirit Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 3/2. 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 4/3010:15 am
MDW
- SJO
1 stop9h 45m
Southwest
Tue 5/51:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/2![Southwest logo]()
$403
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 March 7, 2026.
Search for one-way flight options from Chicago to Costa Rica. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:40 am
ORD
- SJO
1 stop9h 38m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$128
This Frontier deal was found by Cheapflights users on 3/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
ORD
- SJO
1 stop7h 57m
Frontier
Deal found 3/5![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$139
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:21 pm
ORD
- SJO
2 stops20h 53m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$144
This CheapOair deal was found by Cheapflights users on 3/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$145
This CheapOair deal was found by Cheapflights users on 3/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:21 pm
ORD
- SJO
2 stops20h 53m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:10 pm
ORD
- SJO
1 stop18h 04m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$151
This Spirit deal was found by Cheapflights users on 3/5. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$153
This Priceline deal was found by Cheapflights users on 3/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:41 pm
MDW
- SJO
1 stop14h 04m
Frontier
Deal found 3/2![Frontier logo]()
$154
This Southwest deal was found by Cheapflights users on 3/5. 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.
Tue 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 3/5![Southwest logo]()
$159
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 March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $324 (Expedia) |
One-way from | $128 (Mytrip) |
Popular in | December |
Cheapest in | September |
Average price | $598 |
Good round-trip deal | $428 or less |
Good one-way deal | $242 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 March 7, 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 - SJO
ORDSJO
Chicago O'Hare Intl
Wed 4/15
3:05 pm-7:08 am
1 stop17h 03m
San José Juan Santamaria Intl
Wed 4/22
5:46 am-1:13 am
1 stop18h 27m
$430
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 4/17
3:05 pm-9:05 am
1 stop19h 00m
San José Juan Santamaria Intl
Mon 4/27
6:19 pm-1:50 pm
1 stop18h 31m
$430
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 4/8
3:05 pm-9:05 am
1 stop19h 00m
San José Juan Santamaria Intl
Wed 4/15
4:09 am-1:50 pm
1 stop8h 41m
$430
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 4/21
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Fri 5/1
9:00 am-10:45 pm
2 stops12h 45m
$440
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 5/16
4:00 pm-5:30 am
1 stop14h 30m
San José Juan Santamaria Intl
Sun 5/24
11:13 am-9:36 pm
1 stop9h 23m
$462
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 5/29
5:35 am-12:10 pm
1 stop7h 35m
San José Juan Santamaria Intl
Thu 6/4
1:40 pm-11:00 pm
1 stop8h 20m
$464
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Mon 4/13
6:55 am-1:15 pm
1 stop7h 20m
Liberia
Wed 4/15
2:10 pm-11:05 pm
1 stop7h 55m
$466
ChicagoLiberia
ORD - LIR
ORDLIR
Chicago O'Hare Intl
Tue 5/12
6:00 am-12:00 pm
1 stop7h 00m
Liberia
Wed 5/13
1:25 pm-11:59 pm
1 stop9h 34m
$488
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 5/25
5:30 am-12:21 pm
1 stop7h 51m
San José Juan Santamaria Intl
Fri 5/29
12:30 am-10:20 am
1 stop8h 50m
$488
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 4/8
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Wed 4/15
9:00 am-7:45 pm
2 stops9h 45m
$488
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, October is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $247). Flying from Chicago to Costa Rica in April is currently the most expensive (average of $347). 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 March 7, 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 175 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?
Tuesday tends to have the lowest number of delays on this route, whereas Wednesday 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 14% of flights being delayed.
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 March 7, 2026.
Read reviews from past customers who have flown Southwest, Copa Airlines, and United 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 March 7, 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 2,558,603 searches. Data last updated March 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$385 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$589 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$466 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$340 | Average$617 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$386 | Average$626 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$390 | Average$632 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$394 | Average$599 | FlexibilityNo cancel fee | On-time63% |