$207+ Cheap flights from Midway (MDW) to Costa Rica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
juni 12 — juni 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Midway to Costa Rica
Cheapest
Best
Last-minute
One-way
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 maj 13, 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 maj 13, 2026.
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 11/37:00 am
MDW
- LIR
1 stop6h 50m
Southwest
ons. 11/112:45 pm
LIR
- MDW
1 stop8h 20m
Southwest
Deal found 5/12![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 8/196:15 am
MDW
- SJO
1 stop7h 30m
Southwest
tor. 8/279:00 am
SJO
- MDW
1 stop8h 00m
Southwest
Deal found 5/11![Southwest logo]()
$454
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre. 7/243:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
tor. 8/279:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/11![Frontier logo]()
$479
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 10/216:00 am
MDW
- SJO
1 stop6h 58m
Delta
ons. 10/281:23 pm
SJO
- MDW
1 stop7h 22m
Delta
Deal found 5/11![Delta logo]()
$482
This Frontier deal was found by Cheapflights users on 5/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre. 8/73:22 pm
MDW
- SJO
2 stops17h 58m
Frontier
lør. 8/159:35 am
SJO
- MDW
2 stops11h 33m
Frontier
Deal found 5/9![Frontier logo]()
$485
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 8/236:05 am
MDW
- SJO
1 stop6h 44m
Delta
søn. 9/61:21 pm
SJO
- MDW
2 stops22h 09m
Delta
Deal found 5/11![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 8/247:55 am
MDW
- SJO
2 stops11h 45m
Southwest
ons. 9/239:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 5/11![Southwest logo]()
$488
This Frontier deal was found by Cheapflights users on 5/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 8/203:02 pm
MDW
- SJO
2 stops18h 18m
Frontier
man. 8/249:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/8![Frontier logo]()
$505
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 8/233:02 pm
MDW
- SJO
2 stops18h 18m
Frontier
lør. 8/299:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/11![Frontier logo]()
$508
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 8/233:02 pm
MDW
- SJO
2 stops18h 18m
Frontier
søn. 9/69:35 am
SJO
- MDW
2 stops11h 36m
Frontier
Deal found 5/11![Frontier logo]()
$513
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 10/15:05 am
MDW
- SJO
1 stop7h 55m
Southwest
lør. 10/101:00 pm
SJO
- MDW
1 stop8h 15m
Southwest
Deal found 5/11![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
lør. 10/31:00 pm
SJO
- MDW
1 stop8h 15m
Southwest
Deal found 5/11![Southwest logo]()
$519
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 maj 13, 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 maj 13, 2026.
This Delta deal was found by Cheapflights users on 5/8. 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.
tir. 10/276:00 am
MDW
- SJO
1 stop6h 58m
Delta
ons. 10/281:23 pm
SJO
- MDW
1 stop7h 22m
Delta
Deal found 5/8![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 8/247:55 am
MDW
- SJO
2 stops11h 45m
Southwest
ons. 9/239:00 am
SJO
- MDW
2 stops10h 10m
Southwest
Deal found 5/11![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 10/15:05 am
MDW
- SJO
1 stop7h 55m
Southwest
lør. 10/101:00 pm
SJO
- MDW
1 stop8h 15m
Southwest
Deal found 5/11![Southwest logo]()
$514
This Delta deal was found by Cheapflights users on 5/10. 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.
lør. 9/196:00 am
MDW
- SJO
1 stop6h 54m
Delta
lør. 9/261:25 pm
SJO
- MDW
1 stop7h 21m
Delta
Deal found 5/10![Delta logo]()
$566
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 8/2310:15 am
MDW
- SJO
2 stops9h 25m
Southwest
søn. 9/612:35 pm
SJO
- MDW
1 stop9h 20m
Southwest
Deal found 5/11![Southwest logo]()
$519
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 5/2712:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
ons. 6/39:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Deal found 5/12![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 5/9. 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.
tor. 8/1310:05 am
MDW
- SJO
2 stops9h 35m
Southwest
søn. 8/239:00 am
SJO
- MDW
1 stop11h 20m
Southwest
Deal found 5/9![Southwest logo]()
$587
This Delta deal was found by Cheapflights users on 5/9. 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.
tir. 6/306:00 am
MDW
- LIR
1 stop7h 00m
Delta
tir. 7/71:25 pm
LIR
- MDW
1 stop7h 50m
Delta
Deal found 5/9![Delta logo]()
$761
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 6/912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
tir. 6/168:45 am
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 5/12![Southwest logo]()
$617
This Delta deal was found by Cheapflights users on 5/9. 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.
man. 7/66:00 am
MDW
- LIR
1 stop7h 00m
Delta
man. 7/131:25 pm
LIR
- MDW
1 stop7h 50m
Delta
Deal found 5/9![Delta logo]()
$791
This Southwest deal was found by Cheapflights users on 5/8. 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.
lør. 6/205:05 am
MDW
- SJO
1 stop6h 55m
Southwest
fre. 6/261:40 pm
SJO
- MDW
2 stops10h 20m
Southwest
Deal found 5/8![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 7/66:00 am
MDW
- LIR
1 stop7h 00m
Delta
søn. 7/121:25 pm
LIR
- MDW
1 stop7h 50m
Delta
Deal found 5/11![Delta logo]()
$871
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 6/210:15 am
MDW
- SJO
1 stop9h 45m
Southwest
man. 6/88:45 am
SJO
- MDW
2 stops12h 10m
Southwest
Deal found 5/12![Southwest logo]()
$670
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 6/37:25 am
MDW
- LIR
1 stop6h 50m
Southwest
ons. 6/102:10 pm
LIR
- MDW
1 stop8h 40m
Southwest
Deal found 5/12![Southwest logo]()
$678
This Southwest deal was found by Cheapflights users on 5/8. 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.
man. 7/65:00 am
MDW
- LIR
2 stops9h 10m
Southwest
søn. 7/1211:50 am
LIR
- MDW
2 stops18h 20m
Southwest
Deal found 5/8![Southwest logo]()
$773
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 6/118:50 pm
MDW
- LIR
2 stops17h 20m
Southwest
tor. 6/182:10 pm
LIR
- MDW
1 stop7h 50m
Southwest
Deal found 5/12![Southwest logo]()
$885
This Southwest deal was found by Cheapflights users on 5/8. 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.
man. 6/299:55 pm
MDW
- LIR
2 stops16h 15m
Southwest
søn. 7/512:35 pm
LIR
- MDW
1 stop10h 05m
Southwest
Deal found 5/8![Southwest logo]()
$894
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 6/107:10 am
MDW
- LIR
1 stop7h 00m
Southwest
tir. 6/162:10 pm
LIR
- MDW
1 stop8h 40m
Southwest
Deal found 5/11![Southwest logo]()
$909
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated maj 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated maj 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 5/1412:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
man. 5/189:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 5/12![Southwest logo]()
$535
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 5/2712:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
ons. 6/39:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Deal found 5/12![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 5/2810:15 am
MDW
- SJO
1 stop9h 45m
Southwest
ons. 6/39:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Deal found 5/11![Southwest logo]()
$631
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 5/286:55 am
MDW
- LIR
1 stop7h 20m
Southwest
lør. 6/612:15 pm
LIR
- MDW
1 stop9h 10m
Southwest
Deal found 5/12![Southwest logo]()
$719
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 5/286:55 am
MDW
- LIR
1 stop7h 20m
Southwest
ons. 6/32:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 5/11![Southwest logo]()
$729
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 6/28:55 pm
MDW
- LIR
2 stops17h 20m
Southwest
tir. 6/162:10 pm
LIR
- MDW
1 stop8h 40m
Southwest
Deal found 5/11![Southwest logo]()
$773
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 6/37:25 am
MDW
- LIR
1 stop6h 50m
Southwest
ons. 6/102:10 pm
LIR
- MDW
1 stop8h 40m
Southwest
Deal found 5/12![Southwest logo]()
$678
This Southwest deal was found by Cheapflights users on 5/8. 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.
tor. 6/410:10 am
MDW
- SJO
1 stop10h 30m
Southwest
ons. 6/101:40 pm
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 5/8![Southwest logo]()
$549
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 6/65:05 am
MDW
- LIR
1 stop6h 45m
Southwest
tir. 6/92:10 pm
LIR
- MDW
2 stops14h 00m
Southwest
Deal found 5/11![Southwest logo]()
$733
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 6/912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
tir. 6/168:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Deal found 5/12![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 5/10. 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.
tir. 6/97:10 am
MDW
- LIR
1 stop7h 00m
Southwest
tir. 6/162:10 pm
LIR
- MDW
1 stop8h 40m
Southwest
Deal found 5/10![Southwest logo]()
$759
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 6/306:00 am
MDW
- LIR
1 stop7h 00m
Delta
tir. 7/71:25 pm
LIR
- MDW
1 stop7h 50m
Delta
Deal found 5/11![Delta logo]()
$761
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 maj 13, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated maj 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 10/206:40 am
MDW
- SJO
2 stops26h 15m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 7/2810:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Deal found 5/11![Southwest logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 8/812:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/10![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 7/296:00 am
MDW
- SJO
2 stops27h 20m
Frontier
Deal found 5/10![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 7/2812:11 pm
MDW
- SJO
2 stops28h 00m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 10/146:40 am
MDW
- SJO
2 stops33h 31m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 10/136:40 am
MDW
- SJO
2 stops26h 15m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 6/312:04 pm
MDW
- SJO
2 stops28h 07m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 5/10. 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.
man. 8/107:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 5/10![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 10/206:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Deal found 5/12![Southwest logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 8/112:11 pm
MDW
- SJO
2 stops21h 09m
Frontier
Deal found 5/10![Frontier logo]()
$256
This eDestinos deal was found by Cheapflights users on 5/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 6/176:00 am
MDW
- SJO
2 stops27h 20m
Frontier
Deal found 5/10![Frontier logo]()
$257
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 maj 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $452 (Southwest) |
One-way from | $207 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $526 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Costa Rica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated maj 13, 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 - SJO
MDWSJO
Chicago Midway
tir. 10/27
6:00 am-11:58 am
1 stop6h 58m
San José Juan Santamaria Intl
ons. 10/28
1:23 pm-9:45 pm
1 stop7h 22m
$482
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
man. 8/24
7:55 am-6:40 pm
2 stops11h 45m
San José Juan Santamaria Intl
ons. 9/23
9:00 am-8:10 pm
2 stops10h 10m
$488
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
tor. 10/1
5:05 am-12:00 pm
1 stop7h 55m
San José Juan Santamaria Intl
lør. 10/10
1:00 pm-10:15 pm
1 stop8h 15m
$514
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
søn. 8/23
10:15 am-6:40 pm
2 stops9h 25m
San José Juan Santamaria Intl
søn. 9/6
12:35 pm-10:55 pm
1 stop9h 20m
$519
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
ons. 5/27
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
ons. 6/3
9:00 am-7:45 pm
1 stop9h 45m
$557
Quickest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
lør. 9/19
6:00 am-11:54 am
1 stop6h 54m
San José Juan Santamaria Intl
lør. 9/26
1:25 pm-9:46 pm
1 stop7h 21m
$566
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
tor. 8/13
10:05 am-6:40 pm
2 stops9h 35m
San José Juan Santamaria Intl
søn. 8/23
9:00 am-9:20 pm
1 stop11h 20m
$587
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
tir. 6/9
12:00 pm-7:40 pm
1 stop8h 40m
San José Juan Santamaria Intl
tir. 6/16
8:45 am-6:15 pm
1 stop8h 30m
$617
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
lør. 6/20
5:05 am-11:00 am
1 stop6h 55m
San José Juan Santamaria Intl
fre. 6/26
1:40 pm-1:00 am
2 stops10h 20m
$650
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
tir. 6/2
10:15 am-7:00 pm
1 stop9h 45m
San José Juan Santamaria Intl
man. 6/8
8:45 am-9:55 pm
2 stops12h 10m
$670
Showing 1-10 of 39 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 maj 13, 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
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Midway to Costa Rica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Costa Rica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Costa Rica by cabin class
Find flights from Midway to Costa Rica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Costa Rica flights
Browse other Midway and Costa Rica flight options. Last updated on maj 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Costa Rica
Discover the top airline that operate flights from Midway to Costa Rica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated maj 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$615 | FlexibilityNo cancel fee | On-time63% |