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
$84 - $136
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop10h 24m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop13h 48m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop10h 24m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
2 stops18h 07m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop10h 24m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
2 stops10h 59m
San Juan Luis Munoz Marin Intl
Tue 5/14
1 stop13h 48m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/7
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Wed 5/15
1 stop16h 57m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/15
1 stop11h 28m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop27h 53m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/21
1 stop11h 49m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/14
1 stop11h 39m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop29h 24m
No data available for this route at this time. Please check back soon.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Food
Crew
Boarding
Overall
Entertainment
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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