
Round-trip from | $208 (Kiwi.com) |
|---|---|
One-way from | $118 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $567 |
Good one-way deal | $292 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/19
10:46 am-11:45 pm
1 stop10h 59m
San Juan Luis Munoz Marin Intl
sex 1/23
3:55 pm-10:22 pm
1 stop8h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/12
11:21 am-11:45 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
sex 1/16
2:15 pm-10:07 pm
1 stop9h 52m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 1/20
6:00 am-2:31 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
sex 1/23
3:55 pm-10:22 pm
1 stop8h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/26
9:50 am-11:10 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
ter 2/3
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 2/2
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
sex 2/6
7:00 am-6:30 pm
1 stop13h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 2/3
10:48 am-8:58 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
qui 2/5
7:30 am-11:59 am
1 stop6h 29m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
qui 2/19
6:10 am-9:50 pm
1 stop13h 40m
San Juan Luis Munoz Marin Intl
ter 2/24
9:05 am-2:45 pm
1 stop7h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 2/9
1:35 pm-12:05 am
2 stops8h 30m
San Juan Luis Munoz Marin Intl
qua 2/18
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 1/13
8:30 am-5:05 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
qua 1/21
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
qua 2/11
8:25 am-5:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
qua 2/18
9:05 am-6:35 pm
1 stop11h 30m
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $128). Flying from Chicago Midway Airport to Puerto Rico 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.
Unlike at noon, when flights are generally more expensive, you can save up to 55% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Chicago Midway Airport to Puerto Rico 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 22% of weekly flights between Chicago and Puerto Rico 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 22% of flights being delayed.
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
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$379 | Average$495 | FlexibilityNo cancel fee | On-time63% |