Cheap flights from Chicago to San Juan

Bing travel utilizes over a billion airfares on a daily basis to bring you Price Predictors, and now we're using that data to uncover cheap flights from Chicago to San Juan every day. Note that deals are compiled on yesterday's lowest airfares and can change often.

Featured flight deal from Chicago to San Juan

• Chicago (MDW) to San Juan (SJU)

  $154 less than average low on record

  $370

  Fares rising

  View dates
  See more: Low fares from Chicago to San Juan

Lowest fares from Chicago to San Juan

Use our flexible travel graph to find the lowest airfare from Chicago to San Juan. Currently the cheapest flight you can find in the next 30 days from Chicago to San Juan departs on 02/14/2012 and returns 02/15/2012 with a low fare of $370.

View complete flexible search for MDW to SJU (modify trip length and dates)