Search and compare flights from Chicago Midway to Puerto Rico

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Flights from Chicago Midway (MDW) to Puerto Rico

8 flights from 3 partners listed by most popular

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  • $246RTincl. taxesGo to website
    Chicago (MDW) to San Juan (SJU)
    Flying with AirTran Airways
    Depart Oct 08 10
    Return Oct 11 10
  • $408RTincl. taxesGo to website
    Chicago (MDW) to San Juan (SJU)
    Flying with Delta Airlines

    Other dates available
    Depart Mar 30 10
    Return Apr 06 10
  • $246RTincl. taxesGo to website
    Chicago (MDW) to San Juan (SJU)
    Depart Apr 07 10
    Return Apr 15 10
    Show me 5 flights from Hotwire(list view)
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Cheap flights from Chicago Midway to Puerto Rico

Puerto Rico Travel Guide

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There’s so much to see and do when your flight to Puerto Rico lands, it’s hard to know where to start....

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