Cheap Flights from Chicago, IL to San Juan from $136

Return flight: San Juan – Chicago
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On Cheapflightsplus.com you will find 1 direct flights from Chicago to San Juan. You can compare airfare deals from 1 airlines and multiple travel sites from $136, book and save on cheap plane tickets and last minute offers. Also check out CHI-SJU flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to San Juan Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $136 (one-way), $233 (round-trip).
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Best Flights from Chicago to San Juan Today

Take a look at the list of non stop flights and flights with layovers from Chicago to San Juan with the lowest price of $136. Take a look at the list of non stop flights from Chicago to San Juan from $136. The fastest direct flight takes 4h 38m. There’re no connecting flights.
Price Departure Arrival Flight Duration Airline Flight
from $136
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09:00
Chicago
O'Hare International
 15:38
San Juan
Luis Munoz Marin Intl
 4h 38m United Airlines
UA1996
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 03, 2025
Full flight schedule will help you in detecting at what time planes fly from Chicago to San Juan. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
09:00 — 15:38
09:00 — 15:38 UA1996 United Airlines
Chicago — San Juan
4h 38m
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from$136
*Departure and arrival times - local. Updated on March 3, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to San Juan depends on and how to choose the most interesting flight option for you.

Distance between Chicago and San Juan is 3314 miles. Time difference between the cities is 2h. Airplanes depart 09:00 to 09:00 from 7 Chicago airports and arrive 09:00 to 09:00 to 2 San Juan airports. Average flight time is 4h 38m.

  • The fastest flight 4h 38m
  • Average flight time 4h 38m
  • The earliest flight 09:00
  • The latest flight 09:00
  • Distance 2060 ml

The cheapest months to travel to San Juan are march (from 136 $), november (from 284 $), january (from 300 $).

The most expensive months are december (from 347 $), february (from 300 $), january (from 300 $).

What is the lowest airfare Chicago to San Juan?

The cheapest plane ticket found by our users is $136. This airfare is for economy class on one-way UA1996 flight by United Airlines for March 4, 2025 which leaves O'Hare International in Chicago at 09:00 am and arrives at San Juan Luis Munoz Marin Intl at 15:38.

Economy class
$136
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Business class
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Popular Airlines on the Route

The flight Chicago — San Juan is served by 1 regular airline . Most of the flights on this route are operated by United Airlines - 1 departures per week at the price of from $ 136 . And the most expensive tickets are offered by United Airlines airline - from $ 136.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA1996 by United Airlines takes 4h 38m and the cheapest is UA1996 by United Airlines for $136.

  • UA - United Airlines
    from $136
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Connecting Flights

There’re no flights with layovers. Try direct flights or departure from nearby cities.

Airports

You can fly from Chicago to San Juan from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $136
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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San Juan airports

  • Isla Grande-SIG
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  • Luis Munoz Marin Intl-SJU
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Airplanes

There are flights to San Juan from Chicago by 1 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

  • Boeing 737-900
    from $136
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Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

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