$142+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Mar 7 — Mar 141
1 adult, Economy
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Find cheap flights from Costa Rica to Chicago 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 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 February 5, 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 February 5, 2026.
This CheapOair deal was found by Cheapflights users on 2/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Tue 3/314:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$302
This CheapOair deal was found by Cheapflights users on 2/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:31 pm
SJO
- ORD
2 stops18h 28m
Spirit Airlines
Tue 4/285:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:00 am
SJO
- ORD
1 stop8h 14m
American Airlines
Tue 2/243:10 pm
ORD
- SJO
Nonstop5h 02m
American Airlines
Deal found 2/5![American Airlines logo]()
$305
This Mytrip deal was found by Cheapflights users on 2/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:00 am
SJO
- ORD
3 stops13h 18m
Multiple Airlines
Wed 2/254:43 pm
ORD
- SJO
2 stops18h 57m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$307
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:35 pm
SJO
- ORD
2 stops11h 12m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$308
This KAYAK deal was found by Cheapflights users on 2/5. 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 2/141:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sat 2/288:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$309
This Ovago deal was found by Cheapflights users on 2/5. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:25 pm
SJO
- MDW
1 stop8h 06m
LATAM Airlines
Wed 2/2512:45 pm
MDW
- SJO
1 stop9h 17m
LATAM Airlines
Deal found 2/5![LATAM Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:20 pm
SJO
- ORD
1 stop16h 04m
American Airlines
Wed 2/253:10 pm
ORD
- SJO
Nonstop5h 02m
American Airlines
Deal found 2/5![American Airlines logo]()
$313
This Travelocity deal was found by Cheapflights users on 2/5. 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 2/214:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop7h 42m
Multiple Airlines
Sat 2/219:18 am
ORD
- SJO
3 stops14h 12m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$318
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 3/35:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Tue 3/108:34 am
ORD
- SJO
1 stop11h 27m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$320
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:19 pm
SJO
- ORD
2 stops24h 57m
Spirit Airlines
Wed 4/15:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$322
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 February 5, 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 February 5, 2026.
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 3/35:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Tue 3/108:34 am
ORD
- SJO
1 stop11h 27m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Mon 3/91:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Mon 3/169:15 pm
ORD
- SJO
1 stop16h 00m
United Airlines
Deal found 2/4![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 2/4. 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 3/77:00 am
SJO
- MDW
1 stop15h 31m
Delta
Tue 3/1010:45 am
MDW
- SJO
1 stop11h 30m
Delta
Deal found 2/4![Delta logo]()
$335
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:00 pm
LIR
- ORD
2 stops31h 36m
Multiple Airlines
Fri 5/88:20 pm
ORD
- LIR
1 stop16h 45m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 2/2. 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 4/291:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Wed 5/612:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 2/2![Southwest logo]()
$450
This Air Canada deal was found by Cheapflights users on 2/5. 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.
Wed 4/11:15 pm
LIR
- ORD
1 stop24h 40m
Air Canada
Wed 4/83:45 pm
ORD
- LIR
1 stop21h 45m
Air Canada
Deal found 2/5![Air Canada logo]()
$471
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:00 pm
LIR
- ORD
2 stops31h 36m
JetBlue
Fri 5/88:31 am
ORD
- LIR
2 stops28h 24m
JetBlue
Deal found 2/3![JetBlue logo]()
$492
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 5/511:20 am
LIR
- ORD
3 stops30h 43m
Alaska Airlines
Fri 5/83:52 pm
ORD
- LIR
2 stops25h 07m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$569
This Copa Airlines deal was found by Cheapflights users on 2/4. 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.
Wed 2/256:08 pm
SJO
- ORD
1 stop18h 23m
Copa Airlines
Sat 3/143:22 pm
ORD
- SJO
1 stop16h 43m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$320
This Copa Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/38:11 am
SJO
- ORD
1 stop15h 53m
Copa Airlines
Sun 3/83:22 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 2/2![Copa Airlines logo]()
$320
This Copa Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 3/59:17 am
SJO
- ORD
2 stops14h 47m
Copa Airlines
Thu 3/123:22 pm
ORD
- SJO
3 stops26h 24m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$330
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 4/28:13 am
SJO
- ORD
1 stop16h 00m
Copa Airlines
Fri 4/103:21 pm
ORD
- SJO
1 stop16h 50m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 2/4. 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.
Tue 5/51:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Sat 5/95:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Deal found 2/4![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 2/5. 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.
Wed 2/187:00 am
SJO
- MDW
1 stop10h 45m
Delta
Sat 2/219:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/5![Delta logo]()
$458
This Copa Airlines deal was found by Cheapflights users on 2/5. 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 3/198:11 am
SJO
- ORD
1 stop15h 53m
Copa Airlines
Sun 3/223:22 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 2/5![Copa Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:00 am
SJO
- MDW
2 stops9h 45m
Southwest
Thu 5/145:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 2/3![Southwest logo]()
$459
This Delta deal was found by Cheapflights users on 2/2. 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 2/192:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Tue 2/249:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/2![Delta logo]()
$486
This Copa Airlines deal was found by Cheapflights users on 2/3. 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 3/185:51 pm
SJO
- ORD
1 stop18h 40m
Copa Airlines
Sun 3/223:22 pm
ORD
- SJO
1 stop16h 43m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$332
This Orbitz deal was found by Cheapflights users on 2/5. 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.
Wed 4/13:10 pm
LIR
- ORD
1 stop23h 05m
Multiple Airlines
Wed 4/810:00 am
ORD
- LIR
2 stops25h 55m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:27 pm
LIR
- ORD
1 stop15h 33m
United Airlines
Wed 6/107:30 am
ORD
- LIR
1 stop7h 55m
United Airlines
Deal found 2/1![United Airlines logo]()
$576
This Southwest deal was found by Cheapflights users on 2/2. 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 5/19:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Sat 5/95:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Deal found 2/2![Southwest logo]()
$482
This Copa Airlines deal was found by Cheapflights users on 2/1. 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 3/235:51 pm
SJO
- ORD
1 stop18h 40m
Copa Airlines
Mon 3/303:28 pm
ORD
- SJO
1 stop16h 37m
Copa Airlines
Deal found 2/1![Copa Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 2/3. 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.
Thu 5/211:25 pm
LIR
- ORD
1 stop9h 34m
Delta
Tue 5/266:00 am
ORD
- LIR
1 stop7h 00m
Delta
Deal found 2/3![Delta logo]()
$491
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:20 pm
LIR
- ORD
1 stop8h 55m
United Airlines
Tue 6/97:30 am
ORD
- LIR
1 stop7h 55m
United Airlines
Deal found 2/1![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Mon 6/88:02 pm
ORD
- LIR
1 stop17h 08m
United Airlines
Deal found 2/1![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 6/53:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Sun 6/78:02 pm
ORD
- LIR
1 stop14h 58m
United Airlines
Deal found 2/1![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:27 pm
LIR
- ORD
1 stop8h 18m
United Airlines
Sun 6/79:21 pm
ORD
- LIR
1 stop13h 39m
United Airlines
Deal found 2/1![United Airlines logo]()
$576
Last-minute flights from Costa Rica to ChicagoDiscover last-minute flight deals from Costa Rica to Chicago. Data last updated February 5, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Chicago. Data last updated February 5, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 2/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/121:31 pm
SJO
- ORD
1 stop7h 42m
Multiple Airlines
Sun 2/156:28 pm
ORD
- SJO
1 stop29h 37m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$323
This KAYAK deal was found by Cheapflights users on 2/5. 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 2/141:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sat 2/288:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$309
This Travelocity deal was found by Cheapflights users on 2/5. 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 2/214:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop7h 42m
Multiple Airlines
Sat 2/219:18 am
ORD
- SJO
3 stops14h 12m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:00 am
SJO
- ORD
1 stop8h 14m
American Airlines
Tue 2/243:10 pm
ORD
- SJO
Nonstop5h 02m
American Airlines
Deal found 2/5![American Airlines logo]()
$305
This Mytrip deal was found by Cheapflights users on 2/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:00 am
SJO
- ORD
3 stops13h 18m
Multiple Airlines
Wed 2/254:43 pm
ORD
- SJO
2 stops18h 57m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$307
This Ovago deal was found by Cheapflights users on 2/5. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:25 pm
SJO
- MDW
1 stop8h 06m
LATAM Airlines
Wed 2/2512:45 pm
MDW
- SJO
1 stop9h 17m
LATAM Airlines
Deal found 2/5![LATAM Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:20 pm
SJO
- ORD
1 stop16h 04m
American Airlines
Wed 2/253:10 pm
ORD
- SJO
Nonstop5h 02m
American Airlines
Deal found 2/5![American Airlines logo]()
$313
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:35 pm
SJO
- ORD
2 stops11h 12m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$308
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 3/35:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Tue 3/108:34 am
ORD
- SJO
1 stop11h 27m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$320
This CheapOair deal was found by Cheapflights users on 2/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Tue 3/314:36 pm
ORD
- SJO
2 stops19h 06m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$302
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:19 pm
SJO
- ORD
2 stops24h 57m
Spirit Airlines
Wed 4/15:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$322
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 February 5, 2026.
Search for one-way flight options from Costa Rica to Chicago. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/41:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$142
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/211:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/412:35 pm
SJO
- ORD
1 stop22h 11m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 2/4. 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.
Fri 2/271:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/61:31 pm
SJO
- ORD
1 stop30h 38m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$152
This OneTravel deal was found by Cheapflights users on 2/2. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/261:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:31 pm
SJO
- ORD
1 stop9h 34m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 3/312:35 pm
SJO
- ORD
1 stop27h 17m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$157
This Mytrip deal was found by Cheapflights users on 2/3. 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.
Wed 3/187:05 am
SJO
- ORD
1 stop11h 58m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$159
This Trip.com deal was found by Cheapflights users on 2/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:05 am
SJO
- MDW
1 stop12h 48m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 2/2. 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 2/261:50 pm
SJO
- MDW
1 stop8h 25m
Southwest
Deal found 2/2![Southwest logo]()
$179
This Air Canada deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:00 pm
LIR
- ORD
1 stop19h 05m
Air Canada
Deal found 2/4![Air Canada logo]()
$179
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 February 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (CheapOair) |
One-way from | $142 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $459 |
Good round-trip deal | $302 or less |
Good one-way deal | $172 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 February 5, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.
Fly from
Costa Rica
Fly to
Chicago
Route
Depart
Return
Price
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 3/3
5:50 am-12:04 am
1 stop18h 14m
Chicago O'Hare Intl
Tue 3/10
8:34 am-7:01 pm
1 stop11h 27m
$320
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 2/25
6:08 pm-12:31 pm
1 stop18h 23m
Chicago O'Hare Intl
Sat 3/14
3:22 pm-7:05 am
1 stop16h 43m
$320
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 3/3
8:11 am-12:04 am
1 stop15h 53m
Chicago O'Hare Intl
Sun 3/8
3:22 pm-8:20 am
1 stop17h 58m
$320
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 3/9
1:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Mon 3/16
9:15 pm-12:15 pm
1 stop16h 00m
$329
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 3/5
9:17 am-12:04 am
2 stops14h 47m
Chicago O'Hare Intl
Thu 3/12
3:22 pm-4:46 pm
3 stops26h 24m
$330
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/2
8:13 am-1:13 am
1 stop16h 00m
Chicago O'Hare Intl
Fri 4/10
3:21 pm-7:11 am
1 stop16h 50m
$332
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 3/19
8:11 am-1:04 am
1 stop15h 53m
Chicago O'Hare Intl
Sun 3/22
3:22 pm-8:20 am
1 stop17h 58m
$332
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 3/18
5:51 pm-1:31 pm
1 stop18h 40m
Chicago O'Hare Intl
Sun 3/22
3:22 pm-7:05 am
1 stop16h 43m
$332
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 3/23
5:51 pm-1:31 pm
1 stop18h 40m
Chicago O'Hare Intl
Mon 3/30
3:28 pm-7:05 am
1 stop16h 37m
$332
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 3/7
7:00 am-10:31 pm
1 stop15h 31m
Chicago Midway
Tue 3/10
10:45 am-9:15 pm
1 stop11h 30m
$335
Showing 1-10 of 55 results
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, October is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $195). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $337). 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 February 5, 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.
Weekly flight availability from Costa Rica to Chicago
Explore weekly flight availability from Costa Rica to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 5, 2026.
The most flights from CR0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How often are flights from Costa Rica to Chicago delayed?
About 10% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 184 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 Monday 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 6% of flights being delayed.
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 February 5, 2026.
Read reviews from past customers who have flown Southwest, Copa Airlines, and United 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.
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different 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 February 5, 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 February 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Costa Rica to Chicago
Discover the top 6 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 February 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$348 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$249 | Average$484 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$311 | Average$447 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$459 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$400 | Average$560 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |