Round-trip from | $180 (eDestinos) |
---|---|
One-way from | $81 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $430 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/23
8:04 am-1:45 pm
Nonstop4h 41m
San Juan Luis Munoz Marin Intl
Wed 4/30
6:35 am-10:58 am
Nonstop5h 23m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 4/17
8:10 am-8:19 pm
1 stop11h 09m
San Juan Luis Munoz Marin Intl
Thu 4/24
6:35 am-10:58 am
Nonstop5h 23m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 4/7
9:50 am-6:28 pm
1 stop7h 38m
San Juan Luis Munoz Marin Intl
Tue 4/8
2:55 am-10:40 am
1 stop8h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/25
6:15 am-3:22 pm
1 stop8h 07m
San Juan Luis Munoz Marin Intl
Fri 5/2
6:00 am-5:28 pm
1 stop12h 28m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 4/26
1:26 pm-10:02 pm
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Tue 4/29
3:28 am-12:13 pm
1 stop9h 45m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/22
1:50 pm-11:48 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Sat 4/26
7:15 am-4:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:04 am-2:19 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
3:34 pm-10:22 pm
1 stop7h 48m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:35 am-6:50 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
1:00 pm-5:20 pm
Nonstop5h 20m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/15
7:00 pm-8:26 am
1 stop12h 26m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/8
6:00 am-4:05 pm
1 stop9h 05m
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan (average of $254). Flying from Chicago to San Juan in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 29% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to PR1 are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
In terms of precipitation, rainfall in San Juan ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan when rainfall is around 2.2 in.
If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$124 | Average$269 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$144 | Average$274 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$235 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$267 | Average$526 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$293 | Average$400 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$332 | Average$515 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$342 | Average$482 | FlexibilityNo cancel fee | On-time63% |