Find a great deal and save up to 17% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago Midway Airport to Puerto Rico within the next two weeks, with the cheapest ticket starting at $270.
Due to multiple factors, expect to potentially pay more when booking in March. For low rates, September can be a great choice for travel to Puerto Rico. Flights to Puerto Rico from Chicago Midway Airport in September are about $370 on average during September, but can be found for as low as $111.
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.
Fly from
Fly to
Budget
$186 - $207
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 5/4
1 stop12h 29m
San Juan Luis Munoz Marin Intl
Sat 5/11
1 stop8h 50m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/8
1 stop12h 31m
San Juan Luis Munoz Marin Intl
Sat 5/11
1 stop10h 02m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/12
1 stop12h 21m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop7h 31m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/12
1 stop12h 21m
San Juan Luis Munoz Marin Intl
Thu 5/16
1 stop12h 10m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 5/5
1 stop12h 21m
San Juan Luis Munoz Marin Intl
Tue 5/7
1 stop9h 49m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/29
1 stop9h 38m
San Juan Luis Munoz Marin Intl
Wed 5/8
1 stop9h 44m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/8
1 stop12h 31m
San Juan Luis Munoz Marin Intl
Sun 5/12
1 stop20h 28m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/10
1 stop12h 17m
San Juan Luis Munoz Marin Intl
Sun 5/12
1 stop20h 28m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Mon 5/13
1 stop15h 46m
San Juan Luis Munoz Marin Intl
Sun 5/19
1 stop14h 20m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
My flight is always delayed to Las Vegas And the seats always so uncomfortable
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