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
$135 - $316
Route
Depart
Return
Price
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 stop18h 04m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop29h 24m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/15
1 stop9h 38m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop29h 24m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/18
1 stop10h 15m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/20
1 stop12h 21m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/11
1 stop16h 25m
San Juan Luis Munoz Marin Intl
Fri 5/17
Nonstop5h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/30
Nonstop4h 43m
San Juan Luis Munoz Marin Intl
Wed 5/15
2 stops20h 23m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/4
Nonstop4h 43m
San Juan Luis Munoz Marin Intl
Sat 5/11
1 stop8h 01m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/4
2 stops17h 45m
San Juan Luis Munoz Marin Intl
Fri 5/10
1 stop18h 10m
No data available for this route at this time. Please check back soon.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Crew
Overall
Comfort
Boarding
Entertainment
Food
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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