$168+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Costa Rica with Cheapflights
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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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/287:55 am -
2 stops11h 50m
Sat 10/31:00 pm -
1 stop8h 15m
Deal found 8/11![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:05 am -
1 stop6h 49m
Mon 10/51:19 pm -
1 stop8h 25m
Deal found 8/12![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 9/2510:05 am -
1 stop9h 40m
Fri 10/29:00 am -
1 stop10h 20m
Deal found 8/11![Southwest logo]()
$468
This Delta deal was found by Cheapflights users on 8/11. 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 11/111:22 pm -
2 stops8h 53m
Sat 11/212:30 pm -
1 stop8h 26m
Deal found 8/11![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2610:25 am -
1 stop8h 40m
Sat 10/31:00 pm -
1 stop8h 15m
Deal found 8/12![Southwest logo]()
$471
This Delta deal was found by Cheapflights users on 8/10. 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 12/46:00 am -
1 stop16h 15m
Fri 12/117:00 am -
1 stop15h 56m
Deal found 8/10![Delta logo]()
$472
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 11/25:15 am -
1 stop7h 05m
Thu 11/121:20 pm -
1 stop9h 35m
Deal found 8/10![Southwest logo]()
$473
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:00 pm -
1 stop9h 15m
Mon 12/77:00 am -
1 stop9h 14m
Deal found 8/12![Delta logo]()
$475
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 10/2112:25 pm -
1 stop8h 15m
Sun 10/259:00 am -
2 stops11h 50m
Deal found 8/10![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 10/2211:05 am -
2 stops9h 35m
Wed 10/281:00 pm -
1 stop9h 10m
Deal found 8/11![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 9/2410:05 am -
1 stop9h 40m
Thu 10/19:00 am -
2 stops10h 10m
Deal found 8/10![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:40 am -
1 stop7h 10m
Wed 11/112:45 pm -
1 stop8h 20m
Deal found 8/7![Southwest logo]()
$560
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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 11/25:10 am -
1 stop8h 05m
Thu 11/122:10 pm -
2 stops10h 55m
Deal found 8/10![Southwest logo]()
$477
This Delta deal was found by Cheapflights users on 8/11. 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.
Mon 11/26:04 am -
1 stop6h 56m
Thu 11/127:00 am -
2 stops11h 04m
Deal found 8/11![Delta logo]()
$634
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:20 am -
1 stop7h 55m
Tue 11/242:10 pm -
2 stops18h 30m
Deal found 8/9![Southwest logo]()
$526
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:00 pm -
2 stops20h 15m
Mon 11/162:45 pm -
2 stops15h 00m
Deal found 8/8![Southwest logo]()
$585
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:04 am -
1 stop6h 41m
Sun 11/12:00 pm -
1 stop8h 33m
Deal found 8/9![Delta logo]()
$666
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:05 am -
2 stops9h 40m
Mon 9/149:00 am -
2 stops9h 30m
Deal found 8/8![Southwest logo]()
$591
This Delta deal was found by Cheapflights users on 8/10. 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 11/86:04 am -
1 stop6h 56m
Sat 11/142:30 pm -
1 stop8h 26m
Deal found 8/10![Delta logo]()
$706
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:25 am -
2 stops9h 15m
Sat 10/109:00 am -
2 stops10h 35m
Deal found 8/8![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 8/11. 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.
Tue 9/16:05 am -
1 stop6h 44m
Tue 9/81:19 pm -
2 stops18h 48m
Deal found 8/11![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/291:00 pm -
2 stops9h 05m
Fri 2/57:05 am -
2 stops11h 32m
Deal found 8/7![Delta logo]()
$721
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:05 pm -
2 stops17h 20m
Mon 11/303:20 pm -
1 stop7h 45m
Deal found 8/8![Southwest logo]()
$662
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 1/296:00 am -
1 stop6h 45m
Sat 2/62:10 pm -
1 stop8h 00m
Deal found 8/12![Delta logo]()
$726
This Southwest deal was found by Cheapflights users on 8/11. 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.
Sun 12/139:45 pm -
2 stops16h 05m
Sun 12/202:50 pm -
2 stops17h 35m
Deal found 8/11![Southwest logo]()
$697
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:00 am -
1 stop6h 45m
Sat 12/53:25 pm -
1 stop7h 31m
Deal found 8/8![Delta logo]()
$746
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/215:25 am -
1 stop9h 05m
Tue 1/263:25 pm -
2 stops14h 20m
Deal found 8/8![Southwest logo]()
$723
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop6h 45m
Sat 12/123:25 pm -
1 stop7h 31m
Deal found 8/12![Delta logo]()
$746
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 10/106:04 am -
1 stop7h 31m
Sat 10/172:00 pm -
1 stop7h 33m
Deal found 8/11![Delta logo]()
$746
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:25 am -
1 stop9h 05m
Wed 1/273:25 pm -
2 stops14h 20m
Deal found 8/7![Southwest logo]()
$765
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 1/296:00 am -
1 stop6h 45m
Mon 2/87:05 am -
1 stop9h 20m
Deal found 8/12![Delta logo]()
$809
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/41:05 pm -
1 stop9h 00m
Sun 1/177:05 am -
1 stop9h 20m
Deal found 8/8![Delta logo]()
$880
This Delta deal was found by Cheapflights users on 8/10. 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 1/306:00 am -
1 stop6h 45m
Thu 2/42:00 pm -
1 stop8h 10m
Deal found 8/10![Delta logo]()
$887
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop6h 45m
Thu 11/192:00 pm -
1 stop8h 56m
Deal found 8/12![Delta logo]()
$891
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 10/246:04 am -
1 stop7h 31m
Fri 10/301:00 pm -
1 stop8h 33m
Deal found 8/11![Delta logo]()
$896
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated August 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:42 pm -
2 stops18h 18m
Wed 9/231:25 pm -
2 stops18h 42m
Deal found 8/8![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:05 am -
1 stop6h 55m
Sat 9/191:25 pm -
1 stop8h 19m
Deal found 8/8![Delta logo]()
$666
This Southwest deal was found by Cheapflights users on 8/10. 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 9/86:15 am -
1 stop7h 30m
Tue 9/151:40 pm -
1 stop8h 35m
Deal found 8/10![Southwest logo]()
$538
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 9/910:30 am -
1 stop9h 15m
Wed 9/161:40 pm -
1 stop8h 35m
Deal found 8/10![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/1310:15 am -
2 stops9h 25m
Mon 9/281:40 pm -
1 stop7h 40m
Deal found 8/12![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 9/2410:05 am -
1 stop9h 40m
Thu 10/19:00 am -
2 stops10h 10m
Deal found 8/10![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 9/2410:05 am -
2 stops9h 40m
Sun 9/2712:35 pm -
1 stop10h 40m
Deal found 8/10![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 9/2510:05 am -
1 stop9h 40m
Fri 10/29:00 am -
1 stop10h 20m
Deal found 8/11![Southwest logo]()
$468
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2610:25 am -
1 stop8h 40m
Sat 10/31:00 pm -
1 stop8h 15m
Deal found 8/12![Southwest logo]()
$471
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/287:55 am -
2 stops11h 50m
Sat 10/31:00 pm -
1 stop8h 15m
Deal found 8/11![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am -
1 stop7h 30m
Mon 10/59:00 am -
2 stops10h 10m
Deal found 8/8![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:05 am -
1 stop6h 49m
Mon 10/51:19 pm -
1 stop8h 25m
Deal found 8/12![Delta logo]()
$465
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 August 12, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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.
Sun 11/15:15 am -
1 stop7h 05m
Deal found 8/11![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 1/115:25 am -
1 stop8h 20m
Deal found 8/11![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/256:15 am -
1 stop7h 30m
Deal found 8/12![Southwest logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 11/117:25 am -
3 stops42h 00m
Deal found 8/12![Multiple Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop8h 45m
Deal found 8/7![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 8/207:55 am -
2 stops11h 45m
Deal found 8/10![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 8/177:55 am -
2 stops11h 45m
Deal found 8/12![Southwest logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 11/177:25 am -
2 stops25h 30m
Deal found 8/12![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 8/10. 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 9/136:05 am -
1 stop6h 55m
Deal found 8/10![Delta logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Thu 8/2010:25 am -
1 stop27h 00m
Deal found 8/10![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Mon 8/178:23 pm -
2 stops35h 57m
Deal found 8/11![Multiple Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:35 pm -
2 stops17h 15m
Deal found 8/9![Southwest logo]()
$538
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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $455 (Southwest) |
One-way from | $168 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $610 |
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 August 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 11/2
5:10 am-1:15 pm
1 stop8h 05m
San José Juan Santamaria Intl
Thu 11/12
2:10 pm-1:05 am
2 stops10h 55m
$477
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 11/17
5:20 am-1:15 pm
1 stop7h 55m
San José Juan Santamaria Intl
Tue 11/24
2:10 pm-8:40 am
2 stops18h 30m
$526
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Fri 11/6
4:00 pm-12:15 pm
2 stops20h 15m
Liberia
Mon 11/16
2:45 pm-5:45 am
2 stops15h 00m
$585
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Fri 9/11
10:05 am-6:45 pm
2 stops9h 40m
San José Juan Santamaria Intl
Mon 9/14
9:00 am-7:30 pm
2 stops9h 30m
$591
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 11/2
6:04 am-1:00 pm
1 stop6h 56m
San José Juan Santamaria Intl
Thu 11/12
7:00 am-6:04 pm
2 stops11h 04m
$634
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sat 10/3
11:25 am-7:40 pm
2 stops9h 15m
San José Juan Santamaria Intl
Sat 10/10
9:00 am-8:35 pm
2 stops10h 35m
$641
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Tue 11/24
9:05 pm-2:25 pm
2 stops17h 20m
San José Juan Santamaria Intl
Mon 11/30
3:20 pm-11:05 pm
1 stop7h 45m
$662
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Sun 10/25
6:04 am-11:45 am
1 stop6h 41m
Liberia
Sun 11/1
2:00 pm-10:33 pm
1 stop8h 33m
$666
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Sun 12/13
9:45 pm-1:50 pm
2 stops16h 05m
Liberia
Sun 12/20
2:50 pm-8:25 am
2 stops17h 35m
$697
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Sun 11/8
6:04 am-1:00 pm
1 stop6h 56m
San José Juan Santamaria Intl
Sat 11/14
2:30 pm-10:56 pm
1 stop8h 26m
$706
Showing 1-10 of 38 resultsSorted by cheapest first
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
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Costa Rica
Get insights into the airlines that provide service to Costa Rica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Costa Rica. Reviews last updated August 12, 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.
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
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Midway and Costa Rica flights
Browse other Midway and Costa Rica flight options. Last updated on August 12, 2026.
Popular flight searches
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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 August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$729 | FlexibilityNo cancel fee | On-time63% |