Flight Routes from Chicago to San Juan (Puerto Rico)

Compare cheap outbound and return flights from Chicago (CHI) to San Juan (Puerto Rico) (SJU) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€333
Fastest flight
non-stop flights
50x / week
Flight distance
3,318 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL
Most popular airlines
  1. United Airlines
  2. American Airlines
  3. Spirit Airlines
  4. Southwest Airlines

Flight schedule from Chicago (CHI) to San Juan (Puerto Rico) (SJU)

Select a travel date in the flight schedule for the route from Chicago (CHI) to San Juan (Puerto Rico) (SJU) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–SJU · 3 of 3
fromto
dep.arr.
durationstopovers
  1. October 11 – 17, 2026
  2. October 18 – 24, 2026
  3. October 25 – 31, 2026
    1. ORDSJU
      nonstop
      1. Alaska Airlines
    2. ORDSJU
      nonstop
      1. American Airlines
    3. ORDSJU
      nonstop
      1. United Airlines

      Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)

      Favorite airline: American Airlines
      79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.
      American Airlines
      29 %
      Spirit Airlines
      27 %
      United Airlines
      23 %
      Direct flights are the cheapest connection
      On this route, direct flights are $ 2.00 cheaper than flights with a stopover.
      non stop flight
      1 stop
      2 stops
      04h 39min
      13h 20min
      15h 45min
      194 $
      196 $
      451 $
      The favorite connection is non-stop
      Flights from Chicago to San Juan (Puerto Rico) are most often booked as a direct flight.
      Route
      bookings
      Direct flights
      04h 39min, from 194 $
      39 %
      1 stopover Orlando International Airport, FL
      07h 00min, from 221 $
      18 %
      1 stopover Charlotte Douglas International Airport, NC
      13h 01min, from 338 $
      15 %

      Important flight information

      Frequently Asked Questions (FAQ)

      How long is the flight from Chicago to San Juan (Puerto Rico)?
      A nonstop flight from Chicago to San Juan (Puerto Rico) typically takes around 4 hours 48 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 6 hours 16 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
      Are there nonstop flights from Chicago to San Juan (Puerto Rico)?
      Yes, there are nonstop flights from Chicago to San Juan (Puerto Rico), averaging around 4 to 5 flights per day, operated by, among others, United Airlines, American Airlines and Frontier Airlines. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
      Which airlines fly from Chicago to San Juan (Puerto Rico)?
      Direct flights from Chicago to San Juan (Puerto Rico) are operated by, among others, United Airlines, American Airlines and Frontier Airlines. These flights take you to San Juan (Puerto Rico) nonstop, making them especially practical for short trips or weekend getaways. It is still worth comparing departure times and airline policies, as baggage rules and fees can vary.
      On which days are there nonstop flights from Chicago to San Juan (Puerto Rico)?
      Nonstop flights from Chicago to San Juan (Puerto Rico) operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
      How many flights are there per day from Chicago to San Juan (Puerto Rico)?
      On the route from Chicago to San Juan (Puerto Rico), there are on average around 4 to 5 flights per day. The number of flights can vary by day of the week and season. If you are flexible with your dates, it is worth comparing several departure days.
      How many flights per week are there from Chicago to San Juan (Puerto Rico)?
      From Chicago to San Juan (Puerto Rico), there are around 29 to 30 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
      When does the first flight from Chicago to San Juan (Puerto Rico) depart?
      The earliest nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 12:17 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in San Juan (Puerto Rico).
      When does the last flight from Chicago to San Juan (Puerto Rico) depart?
      The last nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 11:53 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.

      Discover more flights around Chicago and San Juan (Puerto Rico)

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
      Destination country Flights to Puerto Rico
      Departure airport - Destination country Chicago-IL, all airports - Puerto Rico
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