Find a great deal and save up to 17% 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 $270.
September is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for September average $370 per person but you can even find prices for as low as $111. The most expensive prices can be found in the month of March. Opting for a September flight can save you 50% 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
$134 - $151
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/9
1 stop11h 59m
San Juan Luis Munoz Marin Intl
Fri 4/12
1 stop12h 51m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/23
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Wed 4/24
1 stop15h 24m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/23
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 5/21
1 stop13h 56m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/23
1 stop12h 07m
San Juan Luis Munoz Marin Intl
Wed 5/8
1 stop13h 56m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/9
1 stop7h 17m
San Juan Luis Munoz Marin Intl
Tue 4/16
1 stop17h 47m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/7
1 stop12h 21m
San Juan Luis Munoz Marin Intl
Tue 5/21
1 stop23h 37m
Chicago O'Hare IntlAguadilla Borinquen
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Mon 4/8
1 stop9h 44m
Aguadilla Borinquen
Tue 4/9
1 stop21h 58m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/16
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 4/23
1 stop23h 54m
Chicago O'Hare IntlAguadilla Borinquen
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 4/17
1 stop16h 20m
Aguadilla Borinquen
Sat 4/27
1 stop23h 14m
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
Boarding
Crew
Food
Overall
Entertainment
Comfort
Reviews
It was a good experience other than a short delay.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
73%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
26%of flight departures | Evening6 pm to midnight |
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