
Round-trip from | $211 (CheapOair) |
|---|---|
One-way from | $122 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $387 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
10:46 am-11:44 pm
1 stop10h 58m
San Juan Luis Munoz Marin Intl
Wed 1/28
7:30 am-12:01 pm
1 stop6h 31m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 1/23
10:53 am-11:44 pm
1 stop10h 51m
San Juan Luis Munoz Marin Intl
Tue 1/27
3:55 pm-10:26 pm
1 stop8h 31m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 1/20
10:53 am-11:44 pm
1 stop10h 51m
San Juan Luis Munoz Marin Intl
Fri 1/23
7:30 am-12:01 pm
1 stop6h 31m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
12:48 pm-11:44 pm
1 stop8h 56m
San Juan Luis Munoz Marin Intl
Wed 2/4
3:55 pm-10:26 pm
1 stop8h 31m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 2/9
1:35 pm-12:05 am
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Thu 2/12
6:30 am-1:20 pm
2 stops8h 50m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 2/3
9:50 am-11:10 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Tue 2/10
6:10 am-11:35 am
1 stop7h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 2/3
10:53 am-8:57 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Sat 2/14
6:15 am-3:23 pm
1 stop11h 08m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Sat 1/31
5:30 am-12:10 pm
1 stop8h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 1/20
2:20 pm-12:35 am
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Fri 1/23
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/14
9:50 am-8:55 pm
2 stops9h 05m
San Juan Luis Munoz Marin Intl
Wed 1/21
6:10 am-11:35 am
1 stop7h 25m
The best time to book flights from Chicago Midway Airport to San Juan is 51 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $127). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $298). 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 Midway Airport to San Juan in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago Midway Airport to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$327 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$299 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$325 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$380 | Average$503 | FlexibilityNo cancel fee | On-time63% |