Find a great deal and save up to 20% 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 $318 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
$128 - $181
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/28
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Tue 6/4
1 stop20h 49m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop7h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/28
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Tue 6/4
Nonstop5h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop11h 28m
San Juan Luis Munoz Marin Intl
Sat 6/1
1 stop9h 00m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/28
1 stop20h 42m
San Juan Luis Munoz Marin Intl
Tue 6/4
2 stops21h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop11h 28m
San Juan Luis Munoz Marin Intl
Wed 5/29
1 stop13h 48m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/21
1 stop11h 28m
San Juan Luis Munoz Marin Intl
Thu 5/30
1 stop11h 48m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/17
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Tue 5/21
1 stop7h 40m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/17
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Haven’t been on a JetBlue flight in years that was on time.
Overall
Boarding
Comfort
Food
Entertainment
Crew
Reviews
Haven’t been on a JetBlue flight in years that was on time.
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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