Find a great deal and save up to 25% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Puerto Rico within the next two weeks, with the cheapest ticket starting at $258.
October is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for October average $319 per person but you can even find prices for as low as $90. The most expensive prices can be found in the month of March. Opting for a October flight can save you 60% on your journey compared to booking in March
When flying from Chicago to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$140 - $344
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop20h 03m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Mon 8/26
2 stops31h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop17h 37m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop15h 01m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/8
1 stop16h 37m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop9h 24m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/28
Nonstop4h 47m
San Juan Luis Munoz Marin Intl
Mon 9/2
1 stop11h 21m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 11/1
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Tue 11/5
1 stop11h 26m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/20
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop9h 50m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Boarding
Entertainment
Comfort
Crew
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
93%of flight departures | Morning6 am to noon |
6%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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