$136+ Cheap flights from Midway (MDW) 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Mar 13 — Mar 201
1 adult, Economy
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Find cheap flights from Midway to Costa Rica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to Costa RicaExplore the most affordable flight options available from Midway to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
Explore the most affordable flight options available from Midway to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:33 pm
MDW
- SJO
1 stop19h 09m
Multiple Airlines
Thu 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$342
This Ovago deal was found by Cheapflights users on 2/7. 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.
Sun 2/226:00 am
MDW
- SJO
1 stop16h 02m
LATAM Airlines
Wed 3/47:00 am
SJO
- MDW
1 stop15h 31m
LATAM Airlines
Deal found 2/7![LATAM Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/410:49 am
MDW
- SJO
1 stop11h 13m
Delta
Wed 3/117:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/11![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Wed 3/187:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/72:56 pm
MDW
- SJO
1 stop19h 44m
Multiple Airlines
Mon 3/1611:38 am
SJO
- MDW
1 stop8h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/56:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Wed 5/131:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 2/10![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 2/7. 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.
Sun 2/229:35 pm
MDW
- LIR
2 stops16h 40m
Southwest
Wed 3/43:25 pm
LIR
- MDW
1 stop7h 30m
Southwest
Deal found 2/7![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:40 pm
MDW
- LIR
2 stops16h 35m
Southwest
Wed 4/292:10 pm
LIR
- MDW
2 stops19h 50m
Southwest
Deal found 2/9![Southwest logo]()
$488
Best flights from Midway to Costa RicaDiscover carefully curated flight deals from Midway to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
Discover carefully curated flight deals from Midway to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:00 am
MDW
- SJO
1 stop16h 02m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 2/7. 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.
Tue 3/35:00 am
MDW
- SJO
1 stop7h 50m
Southwest
Tue 3/101:55 pm
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 2/7![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:49 am
MDW
- SJO
1 stop11h 13m
Delta
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- SJO
1 stop16h 02m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/56:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Tue 5/121:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 2/11![Southwest logo]()
$414
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
MDW
- SJO
1 stop16h 02m
Delta
Wed 3/187:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/9![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 2/7. 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.
Sun 2/229:35 pm
MDW
- LIR
2 stops16h 40m
Southwest
Wed 3/43:25 pm
LIR
- MDW
1 stop7h 30m
Southwest
Deal found 2/7![Southwest logo]()
$481
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:49 am
MDW
- SJO
1 stop11h 13m
Delta
Thu 3/191:20 pm
SJO
- MDW
2 stops18h 33m
Delta
Deal found 2/9![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:40 pm
MDW
- LIR
2 stops16h 35m
Southwest
Wed 4/292:10 pm
LIR
- MDW
2 stops19h 50m
Southwest
Deal found 2/9![Southwest logo]()
$488
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/1710:45 am
MDW
- SJO
1 stop11h 30m
Delta
Wed 3/257:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 2/10![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/178:35 pm
MDW
- LIR
2 stops16h 35m
Southwest
Thu 4/232:10 pm
LIR
- MDW
2 stops18h 45m
Southwest
Deal found 2/10![Southwest logo]()
$497
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/216:00 am
MDW
- SJO
1 stop16h 02m
Delta
Tue 2/247:00 am
SJO
- MDW
1 stop15h 33m
Delta
Deal found 2/10![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/185:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Thu 4/232:10 pm
LIR
- MDW
2 stops18h 45m
Southwest
Deal found 2/10![Southwest logo]()
$497
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/209:34 am
MDW
- SJO
2 stops12h 28m
Delta
Tue 2/247:00 am
SJO
- MDW
1 stop10h 45m
Delta
Deal found 2/10![Delta logo]()
$449
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:55 am
MDW
- LIR
1 stop8h 20m
Southwest
Thu 2/263:10 pm
LIR
- MDW
2 stops17h 40m
Southwest
Deal found 2/9![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/199:34 am
MDW
- SJO
2 stops12h 28m
Delta
Thu 2/262:25 pm
SJO
- MDW
1 stop8h 06m
Delta
Deal found 2/11![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 2/7. 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.
Tue 3/246:25 am
MDW
- LIR
1 stop8h 30m
Southwest
Mon 3/302:05 pm
LIR
- MDW
1 stop7h 45m
Southwest
Deal found 2/7![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:40 pm
MDW
- LIR
1 stop18h 10m
Delta
Tue 3/101:05 pm
LIR
- MDW
1 stop8h 26m
Delta
Deal found 2/9![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/256:36 pm
MDW
- LIR
2 stops18h 24m
Delta
Thu 5/281:25 pm
LIR
- MDW
2 stops18h 18m
Delta
Deal found 2/10![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/176:36 pm
MDW
- LIR
2 stops18h 24m
Delta
Fri 5/221:25 pm
LIR
- MDW
2 stops18h 18m
Delta
Deal found 2/10![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/206:34 pm
MDW
- LIR
1 stop16h 41m
Delta
Thu 3/262:05 pm
LIR
- MDW
1 stop7h 26m
Delta
Deal found 2/10![Delta logo]()
$574
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated February 11, 2026 and is based on user searches.
This Ovago deal was found by Cheapflights users on 2/7. 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.
Sun 2/226:00 am
MDW
- SJO
1 stop16h 02m
LATAM Airlines
Wed 3/47:00 am
SJO
- MDW
1 stop15h 31m
LATAM Airlines
Deal found 2/7![LATAM Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 2/7. 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.
Sun 2/229:35 pm
MDW
- LIR
2 stops16h 40m
Southwest
Wed 3/43:25 pm
LIR
- MDW
1 stop7h 30m
Southwest
Deal found 2/7![Southwest logo]()
$481
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- LIR
1 stop6h 50m
Delta
Thu 2/262:05 pm
LIR
- MDW
1 stop8h 26m
Delta
Deal found 2/9![Delta logo]()
$522
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Wed 3/187:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop8h 21m
Delta
Deal found 2/9![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- SJO
2 stops12h 28m
Delta
Fri 3/67:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:40 pm
MDW
- LIR
1 stop18h 10m
Delta
Tue 3/101:05 pm
LIR
- MDW
1 stop8h 26m
Delta
Deal found 2/9![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Tue 3/107:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/9![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/410:49 am
MDW
- SJO
1 stop11h 13m
Delta
Wed 3/117:00 am
SJO
- MDW
1 stop14h 31m
Delta
Deal found 2/11![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Sat 3/77:00 am
SJO
- MDW
1 stop15h 31m
Delta
Deal found 2/9![Delta logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/72:56 pm
MDW
- SJO
1 stop19h 44m
Multiple Airlines
Mon 3/1611:38 am
SJO
- MDW
1 stop8h 15m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:33 pm
MDW
- SJO
1 stop19h 09m
Multiple Airlines
Thu 4/911:38 am
SJO
- MDW
2 stops27h 21m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$342
One-way flights from Midway to Costa RicaSearch for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:30 pm
MDW
- SJO
1 stop13h 31m
Frontier
Deal found 2/9![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
- SJO
1 stop9h 15m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
MDW
- SJO
3 stops28h 40m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$159
This Trip.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sun 2/156:15 am
MDW
- SJO
1 stop9h 02m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/76:00 am
MDW
- SJO
2 stops29h 22m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/169:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 2/8. 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.
Mon 2/2312:45 pm
MDW
- SJO
1 stop9h 17m
Delta
Deal found 2/8![Delta logo]()
$168
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/259:34 am
MDW
- SJO
2 stops12h 28m
Delta
Deal found 2/9![Delta logo]()
$173
This Trip.com deal was found by Cheapflights users on 2/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:15 am
MDW
- SJO
1 stop9h 15m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/246:10 am
MDW
- SJO
3 stops28h 28m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Trip.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Fri 3/66:00 am
MDW
- SJO
1 stop9h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/1811:00 am
MDW
- LIR
2 stops28h 25m
Porter Airlines
Deal found 2/11![Porter Airlines logo]()
$241
Find flight deals from Midway to Costa Rica
Keep the following information in mind while searching for Midway to Costa Rica flight deals. Data was last updated February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Delta) |
One-way from | $136 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $473 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 February 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.
Fly from
Midway
Fly to
Costa Rica
Route
Depart
Return
Price
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 2/28
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Sat 3/7
7:00 am-3:21 pm
1 stop8h 21m
$358
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/3
10:49 am-10:02 pm
1 stop11h 13m
San José Juan Santamaria Intl
Tue 3/10
7:00 am-10:31 pm
1 stop14h 31m
$364
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 3/1
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Fri 3/6
7:00 am-10:31 pm
1 stop15h 31m
$365
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/3
5:00 am-12:50 pm
1 stop7h 50m
San José Juan Santamaria Intl
Tue 3/10
1:55 pm-11:55 pm
1 stop9h 00m
$378
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 3/6
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Wed 3/18
7:00 am-5:54 pm
2 stops9h 54m
$381
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 5/5
6:00 am-12:10 pm
1 stop7h 10m
San José Juan Santamaria Intl
Tue 5/12
1:10 pm-11:05 pm
1 stop8h 55m
$414
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 3/4
10:49 am-10:02 pm
1 stop11h 13m
San José Juan Santamaria Intl
Thu 3/19
1:20 pm-8:53 am
2 stops18h 33m
$433
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/17
10:45 am-9:15 pm
1 stop11h 30m
San José Juan Santamaria Intl
Wed 3/25
7:00 am-5:54 pm
2 stops9h 54m
$443
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 2/21
6:00 am-10:02 pm
1 stop16h 02m
San José Juan Santamaria Intl
Tue 2/24
7:00 am-10:33 pm
1 stop15h 33m
$444
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 2/20
9:34 am-10:02 pm
2 stops12h 28m
San José Juan Santamaria Intl
Tue 2/24
7:00 am-5:45 pm
1 stop10h 45m
$449
Showing 1-10 of 43 results
Best time to book a flight from Midway to Costa Rica
Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Midway with our price prediction graph.
MDW-SJO
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 Midway Airport to Costa Rica
MDW-CR0
MDW-SJO
MDW-LIR
How often are flights from Chicago to Costa Rica delayed?
About 100% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 97 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 morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday 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.
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 February 11, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Costa Rica have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway 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 Midway 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.
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Find flights from Midway to Costa Rica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Costa Rica flights
Browse other Midway and Costa Rica flight options. Last updated on February 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Costa Rica
Discover the top airline that operate flights from Midway 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$653 | FlexibilityNo cancel fee | On-time63% |