$90+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Apr 24 — May 11
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Costa Rica with Cheapflights
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Cheapest flights from Midway to Costa RicaExplore the most affordable flight options available from Midway to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 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 March 25, 2026.
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$366
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/24![Frontier logo]()
$374
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$376
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/22![Frontier logo]()
$388
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Thu 4/26:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/24![Frontier logo]()
$393
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Fri 5/299:35 am
SJO
- MDW
2 stops35h 27m
Frontier
Deal found 3/21![Frontier logo]()
$395
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:41 pm
MDW
- SJO
1 stop20h 49m
Frontier
Sat 4/412:59 pm
SJO
- MDW
1 stop8h 30m
Frontier
Deal found 3/22![Frontier logo]()
$422
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Wed 4/12:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sun 4/51:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/24![Frontier logo]()
$425
This FlightHub deal was found by Cheapflights users on 3/21. 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.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/21![Frontier logo]()
$426
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/217:25 am
MDW
- LIR
1 stop6h 50m
Southwest
Tue 4/282:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/24![Southwest logo]()
$588
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 5/68:50 pm
MDW
- LIR
2 stops17h 25m
Southwest
Wed 5/132:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/22![Southwest logo]()
$593
This Southwest deal was found by Cheapflights users on 3/23. 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 5/95:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Wed 5/132:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/23![Southwest logo]()
$613
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 March 25, 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 March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/20. 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 5/812:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Wed 5/139:00 am
SJO
- MDW
2 stops10h 00m
Southwest
Deal found 3/20![Southwest logo]()
$488
This Delta deal was found by Cheapflights users on 3/22. 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.
Sun 3/299:35 am
MDW
- SJO
2 stops12h 40m
Delta
Tue 4/71:20 pm
SJO
- MDW
1 stop8h 11m
Delta
Deal found 3/22![Delta logo]()
$822
This Southwest deal was found by Cheapflights users on 3/22. 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 4/2012:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Mon 4/271:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/22![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 3/20. 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 4/2412:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Tue 4/289:00 am
SJO
- MDW
1 stop7h 30m
Southwest
Deal found 3/20![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 3/19. 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.
Sun 5/3111:05 am
MDW
- SJO
2 stops8h 55m
Southwest
Sat 6/612:15 pm
SJO
- MDW
1 stop9h 55m
Southwest
Deal found 3/19![Southwest logo]()
$592
This Southwest deal was found by Cheapflights users on 3/23. 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 5/95:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Wed 5/132:10 pm
LIR
- MDW
2 stops14h 15m
Southwest
Deal found 3/23![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- LIR
1 stop7h 35m
Delta
Fri 4/171:25 pm
LIR
- MDW
1 stop8h 03m
Delta
Deal found 3/22![Delta logo]()
$926
This Southwest deal was found by Cheapflights users on 3/23. 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 5/176:50 am
MDW
- LIR
1 stop7h 20m
Southwest
Fri 5/222:10 pm
LIR
- MDW
2 stops18h 40m
Southwest
Deal found 3/23![Southwest logo]()
$648
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/97:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Sun 5/172:00 pm
SJO
- MDW
2 stops9h 20m
Southwest
Deal found 3/24![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 3/23. 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.
Sat 4/186:00 am
MDW
- LIR
1 stop8h 30m
Delta
Sat 4/251:25 pm
LIR
- MDW
1 stop8h 03m
Delta
Deal found 3/23![Delta logo]()
$956
This Southwest deal was found by Cheapflights users on 3/21. 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 4/157:25 am
MDW
- LIR
1 stop6h 50m
Southwest
Wed 4/222:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/21![Southwest logo]()
$678
This Southwest deal was found by Cheapflights users on 3/21. 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 5/3111:05 am
MDW
- SJO
2 stops8h 55m
Southwest
Sun 6/78:45 am
SJO
- MDW
2 stops10h 45m
Southwest
Deal found 3/21![Southwest logo]()
$695
This Delta deal was found by Cheapflights users on 3/23. 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.
Sat 6/66:23 am
MDW
- LIR
1 stop7h 52m
Delta
Sun 6/141:25 pm
LIR
- MDW
1 stop7h 52m
Delta
Deal found 3/23![Delta logo]()
$1,193
This Southwest deal was found by Cheapflights users on 3/23. 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 5/217:30 am
MDW
- SJO
2 stops12h 30m
Southwest
Sun 5/312:00 pm
SJO
- MDW
2 stops10h 00m
Southwest
Deal found 3/23![Southwest logo]()
$747
This Southwest deal was found by Cheapflights users on 3/22. 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 4/106:55 am
MDW
- LIR
1 stop7h 20m
Southwest
Thu 4/162:10 pm
LIR
- MDW
2 stops18h 45m
Southwest
Deal found 3/22![Southwest logo]()
$753
This Southwest deal was found by Cheapflights users on 3/21. 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 6/106:40 pm
MDW
- LIR
2 stops19h 30m
Southwest
Sun 6/142:05 pm
LIR
- MDW
2 stops18h 15m
Southwest
Deal found 3/21![Southwest logo]()
$773
This Southwest deal was found by Cheapflights users on 3/20. 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.
Wed 4/159:50 am
MDW
- SJO
2 stops10h 10m
Southwest
Tue 4/219:00 am
SJO
- MDW
2 stops11h 45m
Southwest
Deal found 3/20![Southwest logo]()
$807
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:40 am
MDW
- LIR
1 stop7h 30m
Southwest
Mon 6/152:10 pm
LIR
- MDW
2 stops17h 30m
Southwest
Deal found 3/21![Southwest logo]()
$864
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:55 am
MDW
- LIR
1 stop7h 20m
Southwest
Mon 4/132:10 pm
LIR
- MDW
2 stops18h 45m
Southwest
Deal found 3/19![Southwest logo]()
$1,071
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated March 25, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/272:41 pm
MDW
- SJO
1 stop20h 49m
Frontier
Sat 4/412:59 pm
SJO
- MDW
1 stop8h 30m
Frontier
Deal found 3/22![Frontier logo]()
$422
This FlightHub deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Wed 4/12:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sun 4/51:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/24![Frontier logo]()
$425
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Thu 4/26:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/24![Frontier logo]()
$393
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$376
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$374
This FlightHub deal was found by Cheapflights users on 3/21. 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.
Sat 4/42:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/21![Frontier logo]()
$426
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Thu 4/91:27 pm
SJO
- MDW
1 stop29h 40m
Frontier
Deal found 3/23![Frontier logo]()
$366
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Sat 4/1110:06 am
SJO
- MDW
1 stop11h 59m
Frontier
Deal found 3/22![Frontier logo]()
$388
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJO
1 stop22h 16m
Frontier
Fri 5/299:35 am
SJO
- MDW
2 stops35h 27m
Frontier
Deal found 3/21![Frontier logo]()
$395
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:00 am
MDW
- LIR
1 stop8h 10m
Southwest
Fri 4/172:10 pm
LIR
- MDW
2 stops13h 50m
Southwest
Deal found 3/22![Southwest logo]()
$648
This Southwest deal was found by Cheapflights users on 3/23. 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 4/176:55 am
MDW
- LIR
1 stop7h 20m
Southwest
Fri 4/242:10 pm
LIR
- MDW
2 stops18h 40m
Southwest
Deal found 3/23![Southwest logo]()
$633
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/217:25 am
MDW
- LIR
1 stop6h 50m
Southwest
Tue 4/282:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 3/24![Southwest logo]()
$588
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 March 25, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
MDW
- SJO
1 stop7h 12m
Frontier
Deal found 3/22![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 3/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:30 am
MDW
- SJO
1 stop28h 31m
Frontier
Deal found 3/23![Frontier logo]()
$104
This Trip.com deal was found by Cheapflights users on 3/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- SJO
1 stop9h 56m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Wed 5/612:04 pm
MDW
- SJO
2 stops24h 29m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
MDW
- SJO
2 stops24h 34m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Sun 4/125:05 am
MDW
- SJO
2 stops31h 09m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Fri 4/106:30 am
MDW
- SJO
2 stops13h 20m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
MDW
- SJO
1 stop30h 37m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 6/112:46 pm
MDW
- SJO
2 stops21h 47m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 3/20. 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.
Wed 5/67:25 am
MDW
- LIR
1 stop6h 50m
Southwest
Deal found 3/20![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/199:45 pm
MDW
- LIR
2 stops16h 30m
Southwest
Deal found 3/24![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 7/188:10 pm
MDW
- LIR
2 stops17h 55m
Southwest
Deal found 3/24![Southwest logo]()
$308
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 March 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $366 (Justfly.com) |
One-way from | $90 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $598 |
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 March 25, 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
Fri 5/8
12:10 pm-7:00 pm
1 stop7h 50m
San José Juan Santamaria Intl
Wed 5/13
9:00 am-8:00 pm
2 stops10h 00m
$488
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 4/20
12:10 pm-7:00 pm
1 stop7h 50m
San José Juan Santamaria Intl
Mon 4/27
1:10 pm-9:55 pm
1 stop7h 45m
$514
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 4/24
12:10 pm-7:00 pm
1 stop7h 50m
San José Juan Santamaria Intl
Tue 4/28
9:00 am-5:30 pm
1 stop7h 30m
$587
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 5/31
11:05 am-7:00 pm
2 stops8h 55m
San José Juan Santamaria Intl
Sat 6/6
12:15 pm-11:10 pm
1 stop9h 55m
$592
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Sat 5/9
5:00 am-12:10 pm
1 stop8h 10m
Liberia
Wed 5/13
2:10 pm-5:25 am
2 stops14h 15m
$618
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Sun 5/17
6:50 am-1:10 pm
1 stop7h 20m
Liberia
Fri 5/22
2:10 pm-9:50 am
2 stops18h 40m
$648
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 5/9
7:50 am-7:00 pm
2 stops12h 10m
San José Juan Santamaria Intl
Sun 5/17
2:00 pm-12:20 am
2 stops9h 20m
$650
Quickest round-trip
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Wed 4/15
7:25 am-1:15 pm
1 stop6h 50m
Liberia
Wed 4/22
2:10 pm-11:05 pm
1 stop7h 55m
$678
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 5/31
11:05 am-7:00 pm
2 stops8h 55m
San José Juan Santamaria Intl
Sun 6/7
8:45 am-8:30 pm
2 stops10h 45m
$695
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 5/21
7:30 am-7:00 pm
2 stops12h 30m
San José Juan Santamaria Intl
Sun 5/31
2:00 pm-1:00 am
2 stops10h 00m
$747
Showing 1-10 of 37 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
How often are flights from Chicago to Costa Rica delayed?
About 100% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 97 minutes.
What is the most punctual flight time for Chicago to Costa Rica flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
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 March 25, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
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.
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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 March 25, 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 March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$639 | FlexibilityNo cancel fee | On-time63% |