
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $209 (Booking.com) |
One-way from | $109 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $394 |
Good round-trip deal | $686 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/31
8:20 am-2:55 pm
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Tue 2/3
5:40 am-11:15 am
1 stop7h 35m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/31
8:20 am-2:55 pm
Nonstop4h 35m
San Juan Luis Munoz Marin Intl
Wed 2/4
5:40 am-12:30 pm
2 stops8h 50m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/18
9:43 pm-9:54 am
1 stop10h 11m
San Juan Luis Munoz Marin Intl
Thu 1/22
4:11 pm-11:25 pm
1 stop9h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 11/15
2:05 pm-8:45 am
1 stop16h 40m
San Juan Luis Munoz Marin Intl
Sat 11/22
7:10 am-5:15 pm
1 stop12h 05m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 11/18
1:56 pm-9:40 am
2 stops41h 44m
San Juan Luis Munoz Marin Intl
Sun 11/23
5:38 pm-5:15 pm
1 stop25h 37m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/3
8:25 am-5:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 3/7
3:35 pm-6:55 pm
Nonstop5h 20m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 1/30
1:50 pm-12:35 am
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Tue 2/3
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 11/17
9:20 am-11:20 pm
1 stop12h 00m
San Juan Luis Munoz Marin Intl
Fri 11/21
6:40 am-2:10 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 2/9
6:10 am-9:50 pm
1 stop13h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
3:15 pm-12:35 am
1 stop7h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 51 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 $133). Flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport 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 Luis Munoz Marin Intl Airport in the evening. Doing so could potentially save you 38% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport 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.
About 20% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 94 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 20% of flights being delayed.
Atlanta (ATL) – chosen by Cheapflights users on 75% of 1-stop itineraries from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport on Cheapflights.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 7h 00m.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 7h 00m.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 2h 02m.
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Crew
Overall
Food
Entertainment
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$286 | 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% |