Popular in | March |
---|---|
Cheapest in | September |
Round-trip from | $245 |
One-way from | $96 |
Flights from Chicago Midway Airport to San Juan are found to be more expensive on Wednesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San Juan.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 57 days in advance, which can save you up to 25% on flights from Chicago Midway Airport to San Juan compared to booking the week you need them. Waiting 57 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $258. For sooner than that we have options available in the next 3 days from $283.
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 San Juan. Flights to San Juan from Chicago Midway Airport in October are about $319 on average during October, but can be found for as low as $90.
It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 39% on the flight price compared to flying in the afternoon, which is usually more expensive.
Fly from
Fly to
Budget
$227 - $344
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/9
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Tue 7/16
1 stop24h 26m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/9
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Sat 7/13
1 stop12h 30m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/22
1 stop13h 08m
San Juan Luis Munoz Marin Intl
Wed 6/26
1 stop12h 16m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 7/10
1 stop16h 41m
San Juan Luis Munoz Marin Intl
Wed 7/17
1 stop10h 00m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/4
1 stop11h 36m
San Juan Luis Munoz Marin Intl
Thu 7/11
1 stop17h 19m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/29
1 stop23h 51m
San Juan Luis Munoz Marin Intl
Wed 7/3
2 stops13h 18m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/4
2 stops15h 26m
San Juan Luis Munoz Marin Intl
Wed 7/10
1 stop7h 17m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/12
1 stop17h 41m
San Juan Luis Munoz Marin Intl
Tue 6/18
2 stops11h 20m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/20
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Sat 8/24
1 stop8h 27m
SJU Temperature | 77 - 82.4 °F |
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If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Food
Boarding
Entertainment
Overall
Comfort
Crew
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$120 | Average$254 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$167 | Average$267 | FlexibilityNo cancel fee | On-time65% |
Delta | Cheapest$361 | Average$754 | FlexibilityNo cancel fee | On-timeN/A |
Sunday | 2daily flights |
---|---|
Monday | 1daily flight |
Tuesday | 1daily flight |
Wednesday | 1daily flight |
Thursday | 1daily flight |
Friday | 1daily flight |
Saturday | 1daily flight |