
Round-trip from | $199 (Priceline) |
|---|---|
One-way from | $117 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $590 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 2/28
8:00 am-2:53 am
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Sat 3/7
12:07 pm-11:32 pm
1 stop13h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 2/6
1:00 pm-3:26 pm
1 stop24h 26m
San Juan Luis Munoz Marin Intl
Sat 2/14
8:02 pm-2:26 pm
1 stop20h 24m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/25
3:15 pm-12:40 am
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-11:35 am
1 stop7h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 2/19
6:15 am-12:39 pm
1 stop28h 24m
San Juan Luis Munoz Marin Intl
Sun 2/22
3:53 am-8:32 pm
1 stop18h 39m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
9:45 am-9:30 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 2/26
5:30 am-1:30 pm
2 stops10h 00m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 12/15
7:10 am-9:30 pm
1 stop12h 20m
San Juan Luis Munoz Marin Intl
Wed 12/17
8:55 am-4:35 pm
1 stop9h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
1:50 pm-12:35 am
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 1/20
5:00 am-2:55 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 1/26
9:05 am-6:35 pm
1 stop11h 30m
The best time to book flights from Chicago Midway Airport to San Juan is 29 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 $131). 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.
About 23% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 97 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 23% of flights being delayed.
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$271 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$325 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$381 | Average$496 | FlexibilityNo cancel fee | On-time63% |