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 Illinois to Puerto Rico within the next two weeks, with the cheapest ticket starting at $258.
Our data shows that October tends to be the cheapest month to fly to Puerto Rico from Illinois. Users have commonly found prices around $318 for the month, but tickets can be as low as $90. Due to multiple factors, prepare for potentially higher prices in March.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Puerto Rico as you normally would.
Fly from
Fly to
Budget
$137 - $263
Route
Depart
Return
Price
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
Tue 5/21
1 stop12h 38m
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 stop6h 28m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/19
1 stop12h 07m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop16h 05m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/19
1 stop12h 07m
San Juan Luis Munoz Marin Intl
Wed 5/22
1 stop10h 08m
Lambert-St LouisSan Juan Luis Munoz Marin Intl
STL - SJU
STLSJU
Lambert-St Louis
Tue 6/4
1 stop24h 07m
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop22h 22m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 6/1
1 stop16h 51m
San Juan Luis Munoz Marin Intl
Sat 6/8
1 stop8h 21m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/18
1 stop7h 13m
San Juan Luis Munoz Marin Intl
Sun 5/26
Nonstop5h 10m
Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/8
1 stop10h 45m
San Juan Luis Munoz Marin Intl
Fri 5/10
1 stop7h 04m
No data available for this route at this time. Please check back soon.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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.
Overall
Crew
Comfort
Food
Entertainment
Boarding
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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