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: 09/21/2026
From
$198
Seen: 24 minutes ago
One-way
Basic
Chicago (Midway) (MDW)to
Los Cabos (SJD)Depart: 09/13/2026
From
$256
Seen: 4 minutes ago
One-way
Basic
Chicago (Midway) (MDW)to
Puerto Vallarta (PVR)Depart: 09/18/2026
From
$266
Seen: 12 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) | Cancun (CUN) | One-way / Basic | Depart: 11/02/2026 | From $219 Seen: 5 hrs ago |
| Chicago (Midway) (MDW) | Puerto Vallarta (PVR) | One-way / Basic | Depart: 12/12/2026 | From $232 Seen: 8 hrs ago |
| Chicago (Midway) (MDW) | Los Cabos (SJD) | One-way / Basic | Depart: 12/08/2026 | From $249 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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