Southwest® flights from Chicago-Midway to Mexico

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Popular flight deals and low fares from Chicago-Midway

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Chicago-Midway (MDW)to

Cancun (CUN)
Depart: 12/07/2026
From
$242
Seen: 11 hrs ago
One-way
Basic

Chicago-Midway (MDW)to

Los Cabos (SJD)
Depart: 12/06/2026
From
$288
Seen: 21 hrs ago
One-way
Basic

Chicago-Midway (MDW)to

Puerto Vallarta (PVR)
Depart: 12/11/2026
From
$303
Seen: 12 minutes 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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Shop more flights from Chicago-Midway
From
To
Fare Type
Dates
Price
Chicago-Midway (MDW)Cancun (CUN)One-way
/
Basic		Depart: 04/05/2027

From

$237

Seen: 21 hrs ago

Chicago-Midway (MDW)Los Cabos (SJD)One-way
/
Basic		Depart: 02/08/2027

From

$288

Seen: 6 hrs ago

Chicago-Midway (MDW)Puerto Vallarta (PVR)One-way
/
Basic		Depart: 02/18/2027

From

$303

Seen: 15 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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