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
$115 - $359
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Wed 8/28
Nonstop5h 13m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 9/24
1 stop14h 36m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Tue 8/27
2 stops17h 27m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/26
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Wed 8/28
Nonstop5h 13m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/20
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Tue 8/27
1 stop20h 57m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/27
1 stop13h 11m
San Juan Luis Munoz Marin Intl
Tue 8/27
3 stops20h 35m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 9/16
1 stop10h 47m
San Juan Luis Munoz Marin Intl
Thu 10/3
1 stop13h 08m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/5
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Tue 8/13
1 stop10h 08m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/26
1 stop8h 32m
San Juan Luis Munoz Marin Intl
Wed 8/28
1 stop9h 50m
No data available for this route at this time. Please check back soon.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Overall
Entertainment
Boarding
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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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