Southwest® flights from Chicago (Midway) to Costa Rica
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Popular flight deals and low fares from Chicago (Midway)
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Chicago (Midway) (MDW)to
San Jose, Costa Rica (SJO)Depart: 08/31/2026
From
$190
Seen: 15 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Liberia, Costa Rica (LIR)Depart: 08/09/2026
From
$432
Seen: 2 hrs ago
One-way
Choice
*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
Shop more flights from Chicago (Midway)
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From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Chicago (Midway) (MDW) | San Jose, Costa Rica (SJO) | One-way / Basic | Depart: 09/29/2026 | From $190 Seen: 12 hrs ago |
| Chicago (Midway) (MDW) | Liberia, Costa Rica (LIR) | One-way / Basic | Depart: 11/11/2026 | From $233 Seen: 10 hrs ago |
*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
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