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
$106 - $344
Route
Depart
Return
Price
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop20h 09m
San Juan Luis Munoz Marin Intl
Wed 9/11
1 stop22h 07m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Wed 9/11
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Wed 9/11
1 stop15h 16m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Wed 9/11
Nonstop4h 59m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/10
1 stop20h 09m
San Juan Luis Munoz Marin Intl
Wed 9/11
2 stops25h 20m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 9/30
1 stop12h 49m
San Juan Luis Munoz Marin Intl
Mon 10/7
1 stop11h 21m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/9
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Tue 7/16
1 stop24h 26m
Chicago O'Hare IntlAguadilla Borinquen
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Sat 10/12
1 stop8h 24m
Aguadilla Borinquen
Sat 11/2
1 stop8h 34m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/20
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop8h 27m
No data available for this route at this time. Please check back soon.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Entertainment
Overall
Crew
Comfort
Boarding
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$90 | Average$262 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$129 | Average$310 | FlexibilityNo cancel fee | On-time65% |
Delta | Cheapest$135 | Average$555 | FlexibilityNo cancel fee | On-timeN/A |
United Airlines | Cheapest$152 | Average$490 | FlexibilityNo cancel fee | On-time69% |
JetBlue | Cheapest$172 | Average$445 | FlexibilityNo cancel fee | On-time62% |
Alaska Airlines | Cheapest$301 | Average$479 | FlexibilityNo cancel fee | On-time75% |
American Airlines | Cheapest$315 | Average$486 | FlexibilityNo cancel fee | On-time71% |
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 |