Find a great deal and save up to 25% 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 $258.
Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to Puerto Rico. Flights to Puerto Rico from Chicago Midway Airport in October are about $319 on average during October, but can be found for as low as $90.
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
$195 - $373
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/8
1 stop16h 37m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop9h 24m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/5
1 stop17h 41m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop8h 32m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/8
1 stop16h 37m
San Juan Luis Munoz Marin Intl
Wed 6/12
2 stops22h 41m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/13
1 stop11h 32m
San Juan Luis Munoz Marin Intl
Thu 6/20
1 stop20h 01m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 6/11
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop7h 23m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/6
1 stop16h 33m
San Juan Luis Munoz Marin Intl
Sat 6/8
1 stop16h 34m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 6/11
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Thu 6/13
2 stops11h 26m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/8
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Wed 8/14
1 stop8h 16m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/6
1 stop10h 39m
San Juan Luis Munoz Marin Intl
Wed 8/14
1 stop9h 50m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Boarding
Food
Comfort
Crew
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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