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Chicago to Puerto Rico flight

Flying From Chicago to Puerto Rico: What You Need to Know

Cheapest one-way flight price £71
Cheapest return ticket price £144
Off-season travel month April
Peak season for travel June
Popular airline Frontier Airlines
Cheapest month July

Compare multiple airlines at once to find the best flight deals from Chicago to Puerto Rico.

Airlines Flying From Chicago to Puerto Rico
Spirit Airlines logo Spirit Airlines

<h1>Search Flights From Chicago to Puerto Rico</h1>

Easily compare flights from Chicago to Puerto Rico and find the cheapest tickets available!

Find the Cheapest Flights to Puerto Rico From Chicago

Looking for cheap flights from Chicago to Puerto Rico? Check out prices for the next 90 days, starting at just £82 for a one-way ticket and £145 for a round trip.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

FAQs: Flights From Chicago to Puerto Rico

  • When is it the cheapest time to fly from Chicago to Puerto Rico?

    According to our flights calendar over the next 90 days, it seems the cheapest date is on 2025-04-10 for one-way flights.

  • How long does it take to fly to Puerto Rico from Chicago?

    Based on our flight data, the average flight time from Chicago to Puerto Rico is approximately 4 hours 53 minutes based on our most popular routes from Chicago to San Juan. The time may also vary depending on your destination.

  • What is the cheapest airline that flies to Puerto Rico from Chicago?

    The cheapest airline flying to Puerto Rico from Chicago is Frontier Airlines serving route from Chicago to San Juan.

  • Where can I fly to Puerto Rico from Chicago?

    There are direct flights from Chicago to Puerto Rico. San Juan, Aguadilla, and Ponce are all popular destinations in Puerto Rico.

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