$260+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Dec 10 — Dec 171
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 November 10, 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 November 10, 2026.
This Delta deal was found by Cheapflights users on 11/8. 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.
Thu 12/242:24 pm -
1 stop7h 58m
Thu 12/319:29 am -
2 stops12h 17m
Deal found 11/8![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:37 pm -
1 stop8h 17m
Fri 11/2712:05 pm -
2 stops10h 10m
Deal found 11/9![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 11/7. 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.
Thu 11/197:00 am -
2 stops11h 04m
Wed 11/251:05 pm -
1 stop9h 10m
Deal found 11/7![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 11/8. 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.
Thu 11/122:37 pm -
1 stop8h 17m
Thu 11/2611:27 am -
1 stop10h 48m
Deal found 11/8![Delta logo]()
$529
This Travelocity deal was found by Cheapflights users on 11/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:31 pm -
1 stop8h 30m
Thu 12/311:11 pm -
1 stop25h 05m
Deal found 11/8![Frontier logo]()
$537
This Delta deal was found by Cheapflights users on 11/10. 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 12/207:00 am -
1 stop15h 22m
Tue 1/1210:47 am -
1 stop11h 02m
Deal found 11/10![Delta logo]()
$549
This FlightHub deal was found by Cheapflights users on 11/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:31 pm -
1 stop8h 30m
Fri 1/158:13 pm -
1 stop16h 39m
Deal found 11/10![Frontier logo]()
$553
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/131:20 pm -
1 stop9h 40m
Tue 11/175:20 am -
1 stop7h 55m
Deal found 11/6![Southwest logo]()
$559
This Travelocity deal was found by Cheapflights users on 11/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/263:31 pm -
1 stop8h 30m
Thu 12/311:11 pm -
1 stop25h 05m
Deal found 11/9![Frontier logo]()
$562
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 12/252:45 pm -
1 stop8h 25m
Fri 1/16:30 am -
1 stop7h 20m
Deal found 11/9![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 11/9. 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.
Thu 12/242:05 pm -
2 stops15h 40m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/9![Southwest logo]()
$681
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/264:05 pm -
2 stops16h 35m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/6![Southwest logo]()
$737
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 November 10, 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 November 10, 2026.
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/251:50 pm -
1 stop9h 15m
Mon 3/18:50 pm -
2 stops16h 00m
Deal found 11/6![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:37 pm -
1 stop8h 17m
Wed 1/610:47 am -
1 stop11h 02m
Deal found 11/9![Delta logo]()
$657
This Southwest deal was found by Cheapflights users on 11/9. 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 4/209:00 am -
2 stops11h 30m
Tue 4/277:30 am -
2 stops12h 30m
Deal found 11/9![Southwest logo]()
$562
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/212:23 pm -
1 stop9h 32m
Thu 1/289:38 am -
2 stops12h 11m
Deal found 11/5![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 11/9. 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.
Thu 2/113:10 pm -
2 stops18h 20m
Thu 2/189:35 pm -
2 stops16h 40m
Deal found 11/9![Southwest logo]()
$627
This Delta deal was found by Cheapflights users on 11/9. 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.
Thu 2/113:25 pm -
1 stop7h 20m
Fri 2/196:43 pm -
2 stops21h 42m
Deal found 11/9![Delta logo]()
$698
This Southwest deal was found by Cheapflights users on 11/8. 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 12/252:45 pm -
1 stop8h 25m
Fri 1/16:30 am -
1 stop7h 20m
Deal found 11/8![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 11/7. 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.
Wed 12/237:00 am -
1 stop9h 19m
Thu 12/316:00 am -
1 stop6h 59m
Deal found 11/7![Delta logo]()
$726
This Southwest deal was found by Cheapflights users on 11/9. 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.
Thu 12/242:05 pm -
1 stop9h 05m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/9![Southwest logo]()
$681
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/137:00 am -
1 stop9h 55m
Wed 1/209:38 am -
2 stops12h 11m
Deal found 11/6![Delta logo]()
$726
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/192:10 pm -
1 stop8h 15m
Fri 4/237:20 am -
1 stop6h 55m
Deal found 11/9![Southwest logo]()
$701
This Delta deal was found by Cheapflights users on 11/7. 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.
Thu 12/247:00 am -
2 stops10h 44m
Wed 12/309:58 am -
1 stop11h 48m
Deal found 11/7![Delta logo]()
$777
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/264:05 pm -
2 stops16h 35m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/6![Southwest logo]()
$737
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:00 am -
2 stops11h 04m
Wed 12/26:00 am -
1 stop7h 12m
Deal found 11/5![Delta logo]()
$781
This Delta deal was found by Cheapflights users on 11/8. 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.
Thu 12/37:00 am -
2 stops11h 01m
Tue 12/89:37 am -
2 stops12h 40m
Deal found 11/8![Delta logo]()
$794
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:50 pm -
1 stop9h 05m
Sun 1/175:20 am -
1 stop8h 25m
Deal found 11/5![Southwest logo]()
$803
Last-minute flights from Costa Rica to MidwayDiscover last-minute flight deals from Costa Rica to Midway. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Costa Rica to Midway. Data last updated November 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/8. 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.
Thu 11/127:00 am -
2 stops11h 04m
Thu 11/2611:27 am -
1 stop10h 48m
Deal found 11/8![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/131:20 pm -
1 stop9h 40m
Tue 11/175:20 am -
1 stop7h 55m
Deal found 11/6![Southwest logo]()
$559
This Delta deal was found by Cheapflights users on 11/7. 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.
Thu 11/197:00 am -
2 stops11h 04m
Wed 11/251:05 pm -
1 stop9h 10m
Deal found 11/7![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:37 pm -
1 stop8h 17m
Fri 11/2712:05 pm -
2 stops10h 10m
Deal found 11/9![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 11/10. 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 12/207:00 am -
1 stop15h 22m
Tue 1/1210:47 am -
1 stop11h 02m
Deal found 11/10![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 11/8. 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.
Thu 12/242:24 pm -
1 stop7h 58m
Thu 12/319:29 am -
2 stops12h 17m
Deal found 11/8![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 11/9. 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.
Thu 12/242:05 pm -
1 stop9h 05m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/9![Southwest logo]()
$681
This Travelocity deal was found by Cheapflights users on 11/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:31 pm -
1 stop8h 30m
Thu 12/311:11 pm -
1 stop25h 05m
Deal found 11/8![Frontier logo]()
$537
This FlightHub deal was found by Cheapflights users on 11/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:31 pm -
1 stop8h 30m
Fri 1/158:13 pm -
1 stop16h 39m
Deal found 11/10![Frontier logo]()
$553
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 12/252:45 pm -
1 stop8h 25m
Fri 1/16:30 am -
1 stop7h 20m
Deal found 11/9![Southwest logo]()
$645
This Travelocity deal was found by Cheapflights users on 11/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/263:31 pm -
1 stop8h 30m
Thu 12/311:11 pm -
1 stop25h 05m
Deal found 11/9![Frontier logo]()
$562
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/264:05 pm -
2 stops16h 35m
Wed 12/308:35 pm -
2 stops16h 35m
Deal found 11/6![Southwest logo]()
$737
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 November 10, 2026.
Search for one-way flight options from Costa Rica to Midway. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 3/41:05 pm -
1 stop11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Southwest logo]()
$260
This Frontier deal was found by Cheapflights users on 11/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:31 pm -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Frontier logo]()
$276
This Southwest deal was found by Cheapflights users on 11/9. 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 1/273:25 pm -
2 stops14h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 11/9. 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 1/271:50 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/272:00 pm -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 11/9. 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.
Thu 1/283:25 pm -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 3/72:45 pm -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Southwest logo]()
$320
This Mytrip deal was found by Cheapflights users on 11/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:10 pm -
2 stops29h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 11/10. 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 12/223:25 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 11/9. 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.
Sun 2/281:50 pm -
2 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 11/8. 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 2/192:45 pm -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$376
This Mytrip deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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.
Mon 11/307:00 am -
1 stop12h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$383
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (Delta) |
One-way from | $260 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $443 |
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 November 10, 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
Wed 1/27
3:25 pm-5:35 am
2 stops14h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$301
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sun 3/7
2:45 pm-11:25 pm
1 stop8h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$320
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sun 2/28
1:50 pm-8:55 am
2 stops19h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$362
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Fri 2/19
2:45 pm-12:25 am
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$380
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 1/23
1:05 pm-9:45 pm
1 stop8h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$386
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Sun 2/14
3:25 pm-9:45 am
2 stops18h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$395
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 3/27
3:00 pm-11:25 am
2 stops19h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$397
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sun 11/15
2:10 pm-1:10 am
1 stop11h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$398
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Tue 1/26
2:00 pm-11:55 pm
1 stop9h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$405
LiberiaChicago
LIR Liberia - MDW Chicago Midway
LIRMDW
Liberia
Tue 12/15
2:45 pm-11:10 pm
1 stop8h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$406
Showing 1-10 of 36 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, September is the cheapest month in which you can book a flight from Costa Rica to Chicago Midway Airport (average of $437). Flying from Costa Rica to Chicago Midway Airport in March is currently the most expensive (average of $1,078). 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 November 10, 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.
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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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 November 10, 2026.
Costa Rica and Midway flights
Browse other Costa Rica and Midway flight options. Last updated on November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$693 | FlexibilityNo cancel fee | On-time63% |