$188+ Cheap flights from Midway (MDW) to Costa Rica
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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Oct 24 — Oct 311
Round-trip
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 September 24, 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 September 24, 2026.
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/1111:27 am -
1 stop10h 48m
Tue 11/177:00 am -
1 stop9h 18m
Deal found 9/23![Delta logo]()
$418
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop16h 15m
Wed 12/22:37 pm -
2 stops22h 24m
Deal found 9/20![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/315:55 am -
1 stop7h 05m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/23![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/276:04 am -
1 stop6h 56m
Wed 11/42:25 pm -
1 stop8h 08m
Deal found 9/23![Delta logo]()
$465
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.
Sat 10/315:55 am -
1 stop7h 05m
Sat 11/72:05 pm -
1 stop7h 40m
Deal found 9/19![Southwest logo]()
$467
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 11/149:30 am -
2 stops12h 45m
Mon 11/237:00 am -
2 stops11h 04m
Deal found 9/21![Delta logo]()
$470
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 10/2211:50 am -
1 stop8h 50m
Thu 10/299:00 am -
1 stop10h 20m
Deal found 9/22![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/285:55 am -
1 stop8h 55m
Sat 12/52:05 pm -
1 stop7h 35m
Deal found 9/23![Southwest logo]()
$484
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 10/307:50 am -
2 stops12h 50m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/22![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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
Sat 11/72:40 pm -
1 stop7h 45m
Deal found 9/23![Southwest logo]()
$493
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.
Mon 11/305:10 am -
1 stop8h 40m
Wed 12/92:45 pm -
1 stop8h 20m
Deal found 9/20![Southwest logo]()
$527
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 11/168:55 pm -
2 stops16h 55m
Mon 11/232:45 pm -
2 stops14h 55m
Deal found 9/22![Southwest logo]()
$567
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 September 24, 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 September 24, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:04 am -
1 stop6h 56m
Mon 11/22:25 pm -
1 stop8h 08m
Deal found 9/20![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 2/225:00 am -
1 stop7h 50m
Sun 2/282:45 pm -
1 stop9h 10m
Deal found 9/23![Southwest logo]()
$531
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop16h 17m
Tue 12/82:37 pm -
1 stop8h 17m
Deal found 9/20![Delta logo]()
$569
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.
Mon 10/1911:50 am -
1 stop8h 50m
Mon 10/269:00 am -
2 stops13h 15m
Deal found 9/20![Southwest logo]()
$585
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 10/278:15 am -
2 stops12h 25m
Wed 11/41:20 pm -
1 stop8h 00m
Deal found 9/21![Southwest logo]()
$592
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.
Fri 10/306:04 am -
1 stop6h 41m
Wed 11/42:00 pm -
1 stop8h 33m
Deal found 9/21![Delta logo]()
$608
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 1/296:00 am -
1 stop6h 45m
Fri 2/57:05 am -
1 stop9h 20m
Deal found 9/22![Delta logo]()
$616
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.
Sun 10/187:00 am -
1 stop6h 45m
Sun 10/251:45 pm -
2 stops16h 30m
Deal found 9/20![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/138:25 pm -
2 stops17h 20m
Sun 11/222:10 pm -
1 stop11h 00m
Deal found 9/23![Southwest logo]()
$634
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.
Fri 10/306:04 am -
1 stop6h 41m
Thu 11/52:00 pm -
1 stop8h 33m
Deal found 9/21![Delta logo]()
$707
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 1/135:25 am -
1 stop8h 20m
Mon 1/182:45 pm -
1 stop8h 00m
Deal found 9/21![Southwest logo]()
$660
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.
Sat 12/56:00 am -
1 stop8h 10m
Sat 12/123:25 pm -
1 stop7h 29m
Deal found 9/19![Delta logo]()
$716
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/139:40 am -
2 stops11h 00m
Mon 10/191:30 pm -
2 stops10h 40m
Deal found 9/23![Southwest logo]()
$663
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.
Sat 11/286:00 am -
1 stop8h 10m
Sat 12/52:00 pm -
1 stop8h 54m
Deal found 9/19![Delta logo]()
$716
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.
Sat 10/37:00 pm -
2 stops18h 45m
Sat 10/101:45 pm -
1 stop7h 35m
Deal found 9/18![Southwest logo]()
$726
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 11/26:04 am -
1 stop6h 56m
Thu 11/122:37 pm -
1 stop8h 17m
Deal found 9/22![Delta logo]()
$752
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 12/116:30 pm -
2 stops17h 45m
Mon 12/142:45 pm -
2 stops15h 00m
Deal found 9/20![Southwest logo]()
$763
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 1/269:30 am -
2 stops12h 35m
Sun 1/317:05 am -
1 stop9h 20m
Deal found 9/22![Delta logo]()
$801
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.
Wed 11/186:40 am -
1 stop7h 10m
Tue 11/242:50 pm -
2 stops14h 55m
Deal found 9/18![Southwest logo]()
$770
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.
Wed 11/186:44 pm -
2 stops18h 01m
Tue 11/242:00 pm -
2 stops19h 46m
Deal found 9/19![Delta logo]()
$864
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 12/106:40 am -
1 stop7h 10m
Tue 12/152:45 pm -
2 stops15h 00m
Deal found 9/22![Southwest logo]()
$844
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated September 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1911:50 am -
1 stop8h 50m
Thu 10/299:00 am -
2 stops10h 10m
Deal found 9/23![Southwest logo]()
$526
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 10/206:04 am -
1 stop6h 31m
Tue 10/271:00 pm -
1 stop8h 33m
Deal found 9/22![Delta logo]()
$599
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 10/2211:50 am -
1 stop8h 50m
Thu 10/299:00 am -
1 stop10h 20m
Deal found 9/22![Southwest logo]()
$479
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 10/2211:50 am -
1 stop8h 50m
Tue 10/271:00 pm -
1 stop9h 15m
Deal found 9/22![Southwest logo]()
$510
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/2211:50 am -
1 stop8h 50m
Mon 10/269:00 am -
2 stops13h 15m
Deal found 9/23![Southwest logo]()
$514
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop6h 56m
Mon 11/22:25 pm -
2 stops22h 22m
Deal found 9/20![Delta logo]()
$470
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop6h 56m
Tue 11/32:25 pm -
1 stop8h 08m
Deal found 9/20![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/276:04 am -
1 stop6h 56m
Wed 11/42:25 pm -
1 stop8h 08m
Deal found 9/23![Delta logo]()
$465
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 10/307:50 am -
2 stops12h 50m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/22![Southwest logo]()
$488
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.
Fri 10/308:55 pm -
2 stops16h 50m
Thu 11/52:45 pm -
1 stop10h 25m
Deal found 9/21![Southwest logo]()
$579
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/315:55 am -
1 stop7h 05m
Tue 11/32:15 pm -
1 stop8h 50m
Deal found 9/23![Southwest logo]()
$437
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.
Sat 10/315:55 am -
1 stop7h 05m
Sat 11/72:05 pm -
1 stop7h 40m
Deal found 9/19![Southwest logo]()
$467
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 September 24, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$188
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 10/315:55 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$205
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.
Sun 11/2911:00 pm -
2 stops14h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$229
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.
Tue 10/206:04 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$234
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 10/2211:50 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/66:41 pm -
2 stops18h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$240
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.
Sun 10/185:00 am -
2 stops8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$241
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.
Thu 10/226:40 pm -
2 stops38h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$245
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 10/1911:50 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/26:16 am -
3 stops50h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$267
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/319:23 pm -
1 stop14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$269
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.
Wed 10/285:45 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$270
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 September 24, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $418 (Delta) |
One-way from | $188 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $546 |
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 7,457,451 searches. Data last updated September 24, 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 2/1
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$188
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Sun 11/29
11:00 pm-1:50 pm
2 stops14h 50m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
Quickest round-trip
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Tue 10/20
6:04 am-11:35 am
1 stop6h 31m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Sun 10/18
5:00 am-12:45 pm
2 stops8h 45m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$241
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 2/4
5:25 am-1:45 pm
1 stop8h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Mon 2/22
5:00 am-12:50 pm
1 stop7h 50m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$252
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 10/28
5:45 am-12:05 pm
1 stop7h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Thu 12/31
9:23 pm-12:16 pm
1 stop14h 53m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
ChicagoSan José
MDW Chicago Midway - SJO San José Juan Santamaria Intl
MDWSJO
Chicago Midway
Wed 10/21
9:40 am-7:40 pm
2 stops11h 00m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$303
ChicagoLiberia
MDW Chicago Midway - LIR Liberia
MDWLIR
Chicago Midway
Fri 10/16
8:25 pm-12:45 pm
2 stops17h 20m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$312
Showing 1-10 of 41 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 September 24, 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.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 24, 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 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$420 | Average$745 | FlexibilityNo cancel fee | On-time63% |