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1. www.kayak.com › flight-routes › Chicago-CHI$75 Cheap Flights from Chicago to Puerto Rico | KAYAK

   www.kayak.com › flight-routes › Chicago-CHI

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   Find flights to Puerto Rico from $75. Fly from Chicago on Spirit Airlines, Frontier and more. Search for Puerto Rico flights on KAYAK now to find the best deal.

2. www.skyscanner.com › routes › chiaCheap flights from Chicago to Puerto Rico - Skyscanner

   www.skyscanner.com › routes › chia

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   Compare cheap Chicago to Puerto Rico flight deals from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys. Flight tickets to Puerto Rico start from $58 one-way.

3. www.skyscanner.com › routes › ordCheap flights from Chicago O'Hare International to Puerto Rico -...

   www.skyscanner.com › routes › ord

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   Compare cheap Chicago O'Hare International to Puerto Rico flight deals from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys. Flight tickets to Puerto Rico start from $62 one-way.

4. www.momondo.com › flights › chicago$39 Cheap Flights from Chicago to Puerto Rico in 2024 - momondo

   www.momondo.com › flights › chicago

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   The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $124. The fastest flight from Chicago to Puerto Rico takes 4h 40m. Direct flights go from Chicago to Puerto Rico every day.

5. www.skyscanner.net › routes › chiCheap flights from Chicago to Puerto Rico from £108 - Skyscanner

   www.skyscanner.net › routes › chi

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   Looking for a cheap flight from Chicago to Puerto Rico? Compare prices for every major airline, find the best time to fly, then book with no added fees.

6. www.skyscanner.com.au › routes › chiCheap Flights from Chicago to Puerto Rico from $208 | Skyscanner

   www.skyscanner.com.au › routes › chi

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   Compare cheap Chicago to Puerto Rico flight deals from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Puerto Rico start from $99 one-way.

7. www.united.com › en-us › flights-from-chicago-to-puerto-ricoCheap Flights from Chicago to Puerto Rico | United Airlines

   www.united.com › en-us › flights-from-chicago-to-puerto-rico

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   Find United Airlines best fares from Chicago to Puerto Rico. Book a Chicago to Puerto Rico flight and enjoy our premium cabins with speedy Wi-Fi.