
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $193 (CheapOair) |
One-way from | $104 (Trip.com) |
Popular in | June |
Cheapest in | May |
Average price | $359 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 1/29
8:35 am-8:55 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Sat 1/31
8:40 am-4:05 pm
1 stop9h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 2/18
6:00 am-5:27 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Wed 2/25
3:55 pm-10:31 pm
1 stop8h 36m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/13
9:00 am-8:00 pm
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Thu 4/16
3:45 pm-11:40 pm
1 stop8h 55m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 3/4
9:50 am-11:10 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Wed 3/11
5:15 am-12:55 pm
2 stops8h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 2/25
9:50 am-8:55 pm
2 stops9h 05m
San Juan Luis Munoz Marin Intl
Wed 3/4
6:10 am-11:35 am
1 stop7h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/22
1:25 pm-9:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Thu 4/23
5:35 am-12:05 pm
1 stop7h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 2/18
6:50 am-7:05 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Wed 2/25
5:40 am-1:10 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 3/2
1:15 pm-12:40 am
2 stops9h 25m
San Juan Luis Munoz Marin Intl
Tue 3/3
5:40 am-1:10 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 2/26
10:49 am-11:58 pm
1 stop11h 09m
San Juan Luis Munoz Marin Intl
Tue 3/3
6:15 am-11:59 am
1 stop7h 44m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 3/1
2:45 pm-1:05 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Tue 3/10
8:20 pm-9:15 am
1 stop13h 55m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 25 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago Midway Airport 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport (average of $137). Flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport in May 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 Luis Munoz Marin Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
About 29% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 96 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 Tuesday 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 29% of flights being delayed.
Atlanta (ATL) – chosen by Cheapflights users on 80% of 1-stop itineraries from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport on Cheapflights.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $382.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 59m.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 1h 49m.
Entertainment
Comfort
Food
Boarding
Overall
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Food
Boarding
Overall
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Food
Boarding
Overall
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Food
Boarding
Overall
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$298 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$235 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$196 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$379 | Average$492 | FlexibilityNo cancel fee | On-time63% |