$138+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Jul 28 — Aug 41
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Costa Rica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Midway to Costa RicaExplore the most affordable flight options available from Midway to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 28, 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 June 28, 2026.
This Southwest deal was found by Cheapflights users on 6/24. 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 10/315:00 am
MDW
- SJO
1 stop8h 00m
Southwest
Wed 11/42:15 pm
SJO
- MDW
1 stop8h 50m
Southwest
Deal found 6/24![Southwest logo]()
$487
This Southwest deal was found by Cheapflights users on 6/24. 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.
Thu 11/125:15 am
MDW
- SJO
1 stop7h 05m
Southwest
Sun 11/152:10 pm
SJO
- MDW
2 stops10h 55m
Southwest
Deal found 6/24![Southwest logo]()
$489
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- SJO
1 stop6h 44m
Delta
Wed 9/21:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/26![Delta logo]()
$502
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:45 am
MDW
- SJO
1 stop6h 50m
Southwest
Mon 10/261:30 pm
SJO
- MDW
1 stop9h 40m
Southwest
Deal found 6/23![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Tue 11/39:00 am
SJO
- MDW
1 stop10h 35m
Southwest
Deal found 6/28![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 6/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:19 pm
MDW
- SJO
2 stops23h 35m
Delta
Wed 10/211:23 pm
SJO
- MDW
2 stops22h 10m
Delta
Deal found 6/24![Delta logo]()
$507
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Wed 10/289:00 am
SJO
- MDW
2 stops11h 25m
Southwest
Deal found 6/28![Southwest logo]()
$512
This Southwest deal was found by Cheapflights users on 6/24. 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 11/158:40 pm
MDW
- SJO
2 stops15h 40m
Southwest
Thu 11/199:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 6/24![Southwest logo]()
$513
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/2110:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Sun 9/2712:35 pm
SJO
- MDW
1 stop10h 35m
Southwest
Deal found 6/27![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm
MDW
- LIR
2 stops17h 10m
Southwest
Sat 11/141:15 pm
LIR
- MDW
1 stop9h 05m
Southwest
Deal found 6/26![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:45 pm
MDW
- LIR
2 stops16h 05m
Southwest
Sat 11/141:15 pm
LIR
- MDW
1 stop9h 05m
Southwest
Deal found 6/28![Southwest logo]()
$583
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am
MDW
- LIR
1 stop6h 50m
Southwest
Wed 12/92:45 pm
LIR
- MDW
1 stop8h 20m
Southwest
Deal found 6/27![Southwest logo]()
$585
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 June 28, 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 June 28, 2026.
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:45 am
MDW
- SJO
1 stop6h 50m
Southwest
Mon 10/261:30 pm
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 6/23![Southwest logo]()
$508
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Mon 9/71:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/25![Delta logo]()
$611
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/219:20 am
MDW
- SJO
2 stops10h 20m
Southwest
Sun 9/279:00 am
SJO
- MDW
2 stops12h 25m
Southwest
Deal found 6/27![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 6/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am
MDW
- SJO
1 stop6h 58m
Delta
Thu 11/52:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/24![Delta logo]()
$616
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/115:05 am
MDW
- LIR
1 stop6h 45m
Southwest
Wed 7/222:10 pm
LIR
- MDW
1 stop8h 45m
Southwest
Deal found 6/26![Southwest logo]()
$604
This Delta deal was found by Cheapflights users on 6/23. 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.
Thu 8/276:05 am
MDW
- LIR
1 stop6h 55m
Delta
Thu 9/31:25 pm
LIR
- MDW
1 stop8h 11m
Delta
Deal found 6/23![Delta logo]()
$670
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/171:19 pm
MDW
- LIR
2 stops23h 41m
Delta
Wed 9/231:25 pm
LIR
- MDW
2 stops18h 42m
Delta
Deal found 6/27![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/118:10 pm
MDW
- LIR
2 stops17h 55m
Southwest
Sat 7/1811:50 am
LIR
- MDW
2 stops10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$682
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:10 am
MDW
- LIR
1 stop7h 00m
Southwest
Fri 7/102:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 6/23![Southwest logo]()
$683
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/226:05 am
MDW
- LIR
1 stop6h 55m
Delta
Wed 9/231:25 pm
LIR
- MDW
2 stops18h 42m
Delta
Deal found 6/27![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/207:01 pm
MDW
- LIR
2 stops17h 59m
Delta
Thu 9/241:25 pm
LIR
- MDW
1 stop8h 20m
Delta
Deal found 6/27![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/216:42 pm
MDW
- SJO
2 stops18h 07m
Delta
Sat 8/291:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/26![Delta logo]()
$696
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 12/85:15 am
MDW
- SJO
1 stop8h 00m
Southwest
Sun 1/101:50 pm
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 6/27![Southwest logo]()
$783
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 9/226:05 am
MDW
- SJO
1 stop6h 49m
Delta
Wed 10/71:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/25![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/176:05 am
MDW
- SJO
1 stop6h 44m
Delta
Sun 9/61:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/27![Delta logo]()
$720
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/2711:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Mon 8/38:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 6/27![Southwest logo]()
$876
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:30 am
MDW
- SJO
2 stops12h 45m
Delta
Sat 12/127:00 am
SJO
- MDW
2 stops11h 37m
Delta
Deal found 6/25![Delta logo]()
$725
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/235:00 am
MDW
- LIR
2 stops9h 10m
Southwest
Thu 7/302:10 pm
LIR
- MDW
2 stops9h 55m
Southwest
Deal found 6/25![Southwest logo]()
$884
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/236:05 am
MDW
- SJO
1 stop6h 44m
Delta
Wed 8/261:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/26![Delta logo]()
$800
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/166:05 am
MDW
- LIR
1 stop6h 55m
Delta
Wed 8/191:25 pm
LIR
- MDW
1 stop8h 11m
Delta
Deal found 6/25![Delta logo]()
$890
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 12/89:30 am
MDW
- SJO
2 stops12h 45m
Delta
Sun 1/107:05 am
SJO
- MDW
2 stops11h 32m
Delta
Deal found 6/27![Delta logo]()
$908
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 9/166:05 am
MDW
- LIR
1 stop6h 55m
Delta
Sun 9/201:25 pm
LIR
- MDW
1 stop8h 20m
Delta
Deal found 6/26![Delta logo]()
$1,003
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/106:05 am
MDW
- LIR
1 stop6h 55m
Delta
Sat 8/221:25 pm
LIR
- MDW
1 stop8h 11m
Delta
Deal found 6/25![Delta logo]()
$1,003
Last-minute flights from Midway to Costa RicaDiscover last-minute flight deals from Midway to Costa Rica. Data last updated June 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Costa Rica. Data last updated June 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 6/278:30 pm
MDW
- SJO
2 stops23h 10m
Southwest
Wed 7/11:40 pm
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 6/27![Southwest logo]()
$605
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 6/285:05 am
MDW
- SJO
1 stop7h 30m
Southwest
Tue 6/308:45 am
SJO
- MDW
2 stops12h 50m
Southwest
Deal found 6/26![Southwest logo]()
$615
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/211:35 am
MDW
- SJO
1 stop9h 05m
Southwest
Thu 7/91:40 pm
SJO
- MDW
2 stops10h 25m
Southwest
Deal found 6/27![Southwest logo]()
$681
This Frontier deal was found by Cheapflights users on 6/24. 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.
Wed 7/84:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Thu 8/139:35 am
SJO
- MDW
2 stops11h 28m
Frontier
Deal found 6/24![Frontier logo]()
$667
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/115:05 am
MDW
- LIR
1 stop6h 45m
Southwest
Wed 7/222:10 pm
LIR
- MDW
1 stop8h 45m
Southwest
Deal found 6/26![Southwest logo]()
$604
This Southwest deal was found by Cheapflights users on 6/24. 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 7/115:05 am
MDW
- SJO
1 stop6h 55m
Southwest
Sat 7/188:45 am
SJO
- MDW
1 stop14h 00m
Southwest
Deal found 6/24![Southwest logo]()
$617
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/115:05 am
MDW
- LIR
1 stop6h 45m
Southwest
Wed 7/152:10 pm
LIR
- MDW
1 stop8h 45m
Southwest
Deal found 6/25![Southwest logo]()
$637
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/115:05 am
MDW
- LIR
1 stop6h 45m
Southwest
Sat 7/1811:50 am
LIR
- MDW
1 stop10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$677
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/125:05 am
MDW
- LIR
1 stop7h 30m
Southwest
Thu 7/162:10 pm
LIR
- MDW
1 stop7h 55m
Southwest
Deal found 6/25![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/125:05 am
MDW
- LIR
1 stop7h 30m
Southwest
Wed 7/152:10 pm
LIR
- MDW
1 stop8h 45m
Southwest
Deal found 6/25![Southwest logo]()
$678
This Frontier deal was found by Cheapflights users on 6/24. 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.
Wed 7/224:45 pm
MDW
- SJO
2 stops16h 35m
Frontier
Sun 7/269:35 am
SJO
- MDW
2 stops11h 28m
Frontier
Deal found 6/24![Frontier logo]()
$682
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/2711:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Tue 7/288:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Deal found 6/27![Southwest logo]()
$677
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 June 28, 2026.
Search for one-way flight options from Midway to Costa Rica. Find affordable one-way fares based on user searches. Data last updated June 28, 2026.
This Southwest deal was found by Cheapflights users on 6/24. 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.
Mon 9/75:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 6/24![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 6/23. 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 8/710:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 6/23![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 9/86:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/25![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 6/24. 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 9/159:00 am
MDW
- SJO
2 stops10h 40m
Southwest
Deal found 6/24![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/23. 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.
Wed 7/2912:00 pm
MDW
- SJO
1 stop8h 40m
Southwest
Deal found 6/23![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/24. 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.
Tue 9/1512:03 pm
MDW
- SJO
3 stops23h 35m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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.
Tue 10/136:40 am
MDW
- SJO
2 stops33h 31m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/310:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Deal found 6/25![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/27:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 6/27![Southwest logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 8/811:06 am
MDW
- SJO
2 stops22h 14m
Frontier
Deal found 6/24![Frontier logo]()
$288
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/106:42 pm
MDW
- LIR
2 stops18h 18m
Delta
Deal found 6/26![Delta logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:05 am
MDW
- LIR
3 stops55h 25m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$432
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 June 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $487 (Southwest) |
One-way from | $138 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $584 |
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 June 28, 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
Thu 10/22
6:45 am-12:35 pm
1 stop6h 50m
San José Juan Santamaria Intl
Mon 10/26
1:30 pm-12:45 am
2 stops10h 15m
$508
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 9/21
9:20 am-6:40 pm
2 stops10h 20m
San José Juan Santamaria Intl
Sun 9/27
9:00 am-10:25 pm
2 stops12h 25m
$516
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Sat 7/11
5:05 am-10:50 am
1 stop6h 45m
Liberia
Wed 7/22
2:10 pm-11:55 pm
1 stop8h 45m
$604
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 8/31
6:05 am-11:49 am
1 stop6h 44m
San José Juan Santamaria Intl
Mon 9/7
1:14 pm-10:36 pm
1 stop8h 22m
$611
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 10/28
6:00 am-11:58 am
1 stop6h 58m
San José Juan Santamaria Intl
Thu 11/5
2:23 pm-10:10 pm
1 stop7h 47m
$616
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Thu 8/27
6:05 am-12:00 pm
1 stop6h 55m
Liberia
Thu 9/3
1:25 pm-10:36 pm
1 stop8h 11m
$670
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Thu 9/17
1:19 pm-12:00 pm
2 stops23h 41m
Liberia
Wed 9/23
1:25 pm-9:07 am
2 stops18h 42m
$675
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Sat 7/11
8:10 pm-1:05 pm
2 stops17h 55m
Liberia
Sat 7/18
11:50 am-11:15 pm
2 stops10h 25m
$682
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Tue 7/7
7:10 am-1:10 pm
1 stop7h 00m
Liberia
Fri 7/10
2:10 pm-11:05 pm
1 stop7h 55m
$683
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Tue 9/22
6:05 am-12:00 pm
1 stop6h 55m
Liberia
Wed 9/23
1:25 pm-9:07 am
2 stops18h 42m
$689
Showing 1-10 of 33 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-LIR
MDW-SJO
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-LIR
MDW-SJO
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 June 28, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
Complete your trip to Costa Rica by adding a car rental and/or hotel reservation to your travel itinerary.
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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 June 28, 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 June 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$547 | FlexibilityNo cancel fee | On-time63% |