Spirit's Big Front Seats offer 11 inches more legroom, ideal for medium-haul comfort.
Use Spirit's Bag-O-Tron tool to compare baggage fees and save money.
Round-trip from | $227 (CheapOair) |
---|---|
One-way from | $115 (eDestinos) |
Popular in | December |
Cheapest in | September |
Average price | $377 |
Good round-trip deal | $280 or less |
Good one-way deal | $150 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/30
8:47 pm-3:07 pm
1 stop17h 20m
San Juan Luis Munoz Marin Intl
Fri 9/5
3:39 am-3:17 pm
1 stop12h 38m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 9/6
6:44 pm-11:04 am
1 stop15h 20m
San Juan Luis Munoz Marin Intl
Sat 9/13
3:19 pm-9:58 pm
1 stop7h 39m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/30
10:51 am-7:18 pm
1 stop7h 27m
San Juan Luis Munoz Marin Intl
Fri 9/5
3:39 am-9:51 am
1 stop7h 12m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/9
12:20 pm-12:27 am
1 stop11h 07m
San Juan Luis Munoz Marin Intl
Mon 8/11
3:34 am-10:14 am
1 stop7h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 9/19
5:05 am-1:50 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Tue 9/23
1:35 pm-10:25 pm
2 stops9h 50m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 9/8
12:55 pm-6:34 pm
Nonstop4h 39m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/23
10:51 am-7:18 pm
1 stop7h 27m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/9
12:20 pm-12:27 am
1 stop11h 07m
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/9
11:13 am-1:58 am
1 stop13h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 9/22
12:50 pm-2:11 pm
3 stops24h 21m
Booking 42 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Juan Luis Munoz Marin Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan Luis Munoz Marin Intl Airport (average of $254). Flying from Chicago to San Juan Luis Munoz Marin Intl Airport in June is currently the most expensive (average of $339). 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 Luis Munoz Marin Intl Airport in the evening. Doing so could potentially save you 32% 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 Luis Munoz Marin Intl Airport 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 SJU are scheduled on a Saturday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
Orlando (MCO) – chosen by Cheapflights users on 35% of 1-stop itineraries from Chicago to San Juan Luis Munoz Marin Intl Airport on Cheapflights.
Philadelphia (PHL) is the most affordable 1-stop option, with an average round-trip price of $168.
Flights via Tampa (TPA) have the shortest average one-way travel time for 1-stop routes: 3h 45m.
Flights via Tampa (TPA) offer the fastest connection on this route, with an average layover time of 1h 00m.
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Gina,Jul 2025
LAS - DEN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Gina,Jul 2025
LAS - DEN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Gina,Jul 2025
LAS - DEN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Gina,Jul 2025
LAS - DEN
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