
Round-trip from | $197 (Frontier) |
|---|---|
One-way from | $100 (Super.com) |
Popular in | March |
Cheapest in | February |
Average price | $289 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/8
9:14 am-2:01 am
1 stop15h 47m
San Juan Luis Munoz Marin Intl
Mon 5/11
3:18 pm-10:19 pm
1 stop8h 01m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/9
9:20 am-2:01 am
1 stop15h 41m
San Juan Luis Munoz Marin Intl
Mon 4/13
5:45 am-8:09 pm
1 stop15h 24m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/15
12:52 pm-11:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Tue 4/21
12:55 pm-10:28 pm
1 stop10h 33m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
6:00 am-2:37 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Sun 5/10
3:19 pm-8:04 am
1 stop17h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/15
8:35 pm-8:55 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Wed 5/20
3:45 pm-9:25 pm
1 stop6h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
5:00 am-3:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Wed 5/6
11:25 am-7:45 pm
2 stops9h 20m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/9
12:47 pm-8:18 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Wed 4/15
2:45 pm-10:28 pm
1 stop8h 43m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/10
1:25 pm-11:35 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Thu 5/14
10:00 am-5:45 pm
2 stops8h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/11
8:35 pm-10:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Sun 5/17
9:45 pm-11:50 am
2 stops15h 05m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/2
5:00 am-3:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:45 am-1:55 pm
2 stops9h 10m
The best time to book flights from Chicago Midway Airport to San Juan is 55 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $91). 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.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
About 27% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 100 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 27% of flights being delayed.
Overall
Comfort
Crew
Food
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Comfort
Crew
Food
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Comfort
Crew
Food
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Comfort
Crew
Food
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$290 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$379 | Average$487 | FlexibilityNo cancel fee | On-time63% |