$267+ Cheap flights from Costa Rica to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Costa Rica to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Costa Rica to Midway
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Cheapest flights from Costa Rica to MidwayExplore the most affordable flight options available from Costa Rica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Costa Rica to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/51:20 pm -
1 stop9h 40m
Sun 11/85:15 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/122:37 pm -
1 stop8h 17m
Tue 11/179:30 am -
2 stops12h 45m
Deal found 9/22![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/32:15 pm -
1 stop8h 50m
Sun 11/85:15 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/213:25 pm -
1 stop7h 45m
Sun 1/245:25 am -
1 stop8h 20m
Deal found 9/22![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/221:30 pm -
1 stop7h 50m
Sun 10/259:55 am -
2 stops10h 45m
Deal found 9/21![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/72:25 pm -
1 stop8h 08m
Sat 11/1411:27 am -
1 stop10h 48m
Deal found 9/21![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/222:37 pm -
1 stop8h 17m
Sat 12/511:28 am -
1 stop10h 49m
Deal found 9/18![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/269:00 am -
2 stops13h 15m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/18![Southwest logo]()
$499
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/241:00 pm -
1 stop8h 20m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/62:45 pm -
2 stops19h 10m
Fri 11/136:30 pm -
2 stops17h 45m
Deal found 9/22![Southwest logo]()
$585
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/182:50 pm -
1 stop10h 05m
Sun 1/310:55 pm -
2 stops14h 55m
Deal found 9/18![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/172:00 pm -
1 stop7h 33m
Tue 10/276:04 am -
1 stop6h 41m
Deal found 9/22![Delta logo]()
$804
Best flights from Costa Rica to MidwayDiscover carefully curated flight deals from Costa Rica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Costa Rica to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/211:25 pm -
1 stop8h 08m
Wed 11/1111:27 am -
1 stop10h 48m
Deal found 9/22![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/269:00 am -
2 stops13h 15m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/18![Southwest logo]()
$499
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/251:35 pm -
1 stop10h 25m
Sun 11/15:15 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$520
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/229:00 am -
2 stops10h 10m
Tue 10/275:45 am -
1 stop7h 20m
Deal found 9/21![Southwest logo]()
$562
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/201:25 pm -
1 stop8h 08m
Mon 10/266:04 am -
1 stop6h 56m
Deal found 9/19![Delta logo]()
$649
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/159:00 am -
2 stops10h 10m
Thu 10/2911:50 am -
1 stop8h 50m
Deal found 9/17![Southwest logo]()
$578
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/62:45 pm -
1 stop10h 25m
Fri 11/136:30 pm -
2 stops17h 45m
Deal found 9/22![Southwest logo]()
$585
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/182:50 pm -
1 stop10h 05m
Sun 1/310:55 pm -
2 stops14h 55m
Deal found 9/19![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/172:00 pm -
1 stop7h 33m
Tue 10/276:04 am -
1 stop6h 41m
Deal found 9/22![Delta logo]()
$804
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/89:00 am -
1 stop10h 20m
Sun 11/85:15 am -
1 stop7h 05m
Deal found 9/22![Southwest logo]()
$624
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/21:20 pm -
2 stops10h 45m
Mon 11/98:15 pm -
2 stops17h 00m
Deal found 9/18![Southwest logo]()
$674
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/109:00 am -
2 stops21h 25m
Fri 10/2311:50 am -
1 stop8h 50m
Deal found 9/21![Southwest logo]()
$679
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/81:00 pm -
1 stop8h 33m
Mon 10/126:04 am -
1 stop6h 31m
Deal found 9/19![Delta logo]()
$1,115
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/22:15 pm -
1 stop8h 55m
Mon 12/75:20 am -
1 stop7h 55m
Deal found 9/19![Southwest logo]()
$702
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/62:00 pm -
1 stop8h 33m
Fri 11/136:00 am -
1 stop6h 45m
Deal found 9/22![Delta logo]()
$1,235
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/252:10 pm -
1 stop7h 45m
Tue 12/15:20 am -
1 stop7h 55m
Deal found 9/21![Southwest logo]()
$723
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/191:00 pm -
1 stop8h 33m
Tue 10/276:04 am -
1 stop6h 41m
Deal found 9/22![Delta logo]()
$1,328
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 1/92:30 pm -
1 stop8h 10m
Tue 1/125:25 am -
1 stop9h 05m
Deal found 9/22![Southwest logo]()
$782
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 1/283:25 pm -
2 stops14h 20m
Thu 2/47:55 pm -
2 stops18h 20m
Deal found 9/18![Southwest logo]()
$786
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/12:45 pm -
1 stop8h 25m
Wed 12/96:40 am -
1 stop7h 10m
Deal found 9/18![Southwest logo]()
$927
Last-minute flights from Costa Rica to MidwayDiscover last-minute flight deals from Costa Rica to Midway. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Midway. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:25 pm -
1 stop8h 19m
Mon 9/286:05 am -
1 stop6h 55m
Deal found 9/19![Delta logo]()
$936
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/172:00 pm -
1 stop7h 33m
Tue 10/276:04 am -
1 stop6h 41m
Deal found 9/22![Delta logo]()
$804
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/221:30 pm -
1 stop7h 50m
Sun 10/259:55 am -
2 stops10h 45m
Deal found 9/21![Southwest logo]()
$480
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/221:30 pm -
1 stop7h 50m
Tue 10/275:45 am -
1 stop7h 20m
Deal found 9/21![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:30 pm -
1 stop7h 50m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/20![Southwest logo]()
$535
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/241:00 pm -
1 stop8h 20m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/251:35 pm -
1 stop10h 25m
Sun 11/15:15 am -
1 stop7h 05m
Deal found 9/17![Southwest logo]()
$520
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/269:00 am -
2 stops13h 15m
Sat 10/315:55 am -
1 stop7h 05m
Deal found 9/18![Southwest logo]()
$499
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/271:25 pm -
1 stop8h 08m
Sun 11/156:00 am -
1 stop16h 15m
Deal found 9/22![Delta logo]()
$518
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/291:25 pm -
1 stop8h 08m
Sun 11/156:00 am -
1 stop16h 15m
Deal found 9/22![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/291:25 pm -
1 stop8h 08m
Mon 11/166:00 am -
1 stop16h 15m
Deal found 9/22![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/299:00 am -
1 stop10h 20m
Thu 11/55:15 am -
1 stop7h 05m
Deal found 9/22![Southwest logo]()
$539
One-way flights from Costa Rica to MidwaySearch for one-way flight options from Costa Rica to Midway. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Costa Rica to Midway. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/171:30 pm -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/62:10 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/141:30 pm -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Porter Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 12/52:05 pm -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/161:15 pm -
1 stop20h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/201:00 pm -
1 stop8h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/101:30 pm -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Porter Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/201:00 pm -
2 stops9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$320
This Mytrip deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Sun 10/1812:40 pm -
2 stops21h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/213:25 pm -
2 stops17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$340
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sun 10/251:35 pm -
1 stop16h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$348
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Mon 10/269:00 am -
1 stop14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$358
Find flight deals from Costa Rica to Midway
Keep the following information in mind while searching for Costa Rica to Midway flight deals. Data was last updated September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $415 (Southwest) |
One-way from | $267 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $514 |
Cheapflights Fare Finder
Customize your flight search to find flights from Costa Rica to Midway 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 7,457,451 searches. Data last updated September 22, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Sat 10/17
1:30 pm-11:00 am
1 stop20h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
Quickest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Mon 12/21
3:25 pm-11:10 pm
1 stop7h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Fri 10/16
1:15 pm-11:00 am
1 stop20h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$291
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Tue 10/20
1:00 pm-10:33 pm
1 stop8h 33m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$295
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Tue 10/20
7:07 am-11:43 pm
3 stops39h 36m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$359
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Tue 10/20
1:00 pm-11:15 pm
1 stop9h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$360
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Sun 10/11
1:45 pm-1:00 am
1 stop10h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$426
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Fri 10/16
1:30 pm-10:20 pm
1 stop7h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$446
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Thu 12/3
1:16 pm-12:14 pm
3 stops22h 58m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$464
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Tue 12/1
3:10 pm-2:55 pm
3 stops47h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$466
Showing 1-10 of 38 resultsSorted by cheapest first
Best time to book a flight from Costa Rica to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Costa Rica with our price prediction graph.
SJO-MDW
LIR-MDW
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 Midway Airport
CR0-MDW
SJO-MDW
LIR-MDW
What is the cheapest month to book a flight from Costa Rica to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Costa Rica to Chicago Midway Airport (average of $385). Flying from Costa Rica to Chicago Midway Airport in July is currently the most expensive (average of $902). 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.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 22, 2026.
Read reviews from past customers who have flown Southwest from Costa Rica to Chicago Midway Airport. 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Costa Rica to Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Midway flight routes
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Popular flights
Alternative routes for Costa Rica to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Costa Rica to Midway by cabin class
Find flights from Costa Rica to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Costa Rica and Midway flights
Browse other Costa Rica and Midway flight options. Last updated on September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Costa Rica to Midway
Discover the top airline that operate flights from Costa Rica to Midway. 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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$697 | FlexibilityNo cancel fee | On-time63% |