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: 10/26/2026
From
$235
Seen: 14 hrs ago
One-way
Basic

Chicago-Midway (MDW)to

Liberia, Costa Rica (LIR)
Depart: 10/24/2026
From
$318
Seen: 16 hrs ago
One-way
Basic
*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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From
To
Fare Type
Dates
Price
Chicago-Midway (MDW)San Jose, Costa Rica (SJO)One-way
/
Basic		Depart: 01/24/2027

From

$188

Seen: 4 hrs ago

Chicago-Midway (MDW)Liberia, Costa Rica (LIR)One-way
/
Basic		Depart: 01/24/2027

From

$234

Seen: 20 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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