
Round-trip from | $226 (Frontier) |
|---|---|
One-way from | $120 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Wed 4/29
5:35 am-1:45 pm
1 stop9h 10m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/25
9:20 am-5:35 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 5/2
1:10 pm-5:20 pm
Nonstop5h 10m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/3
2:40 pm-11:35 pm
2 stops7h 55m
San Juan Luis Munoz Marin Intl
Wed 5/20
5:35 am-12:10 pm
1 stop7h 35m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/19
1:25 pm-9:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 5/23
5:15 am-6:15 pm
1 stop14h 00m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 5/26
6:23 am-4:33 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Tue 6/2
1:14 pm-9:09 pm
1 stop8h 55m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/27
12:00 pm-11:25 pm
2 stops10h 25m
San Juan Luis Munoz Marin Intl
Fri 5/15
3:45 pm-12:15 am
1 stop9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/8
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Tue 5/12
5:05 am-3:50 pm
2 stops11h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/18
9:20 am-5:35 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 5/15
10:00 am-6:15 pm
2 stops9h 15m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/1
12:52 pm-8:24 pm
1 stop6h 32m
San Juan Luis Munoz Marin Intl
Tue 5/5
6:15 am-4:26 pm
1 stop11h 11m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 6/15
6:05 am-4:46 pm
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Sun 6/21
6:00 am-12:00 pm
1 stop7h 00m
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $91). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $314). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Puerto Rico as you normally would.
About 31% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 110 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 31% of flights being delayed.
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Crew
Comfort
Entertainment
Food
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$377 | Average$491 | FlexibilityNo cancel fee | On-time63% |