Popular in | March |
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Cheapest in | September |
Round-trip from | $244 |
One-way from | $66 |
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 40% on the flight price compared to flying in the afternoon, which is usually more expensive.
Fly from
Fly to
Budget
$130 - $172
Route
Depart
Return
Price
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Fri 6/21
1 stop9h 19m
San Juan Luis Munoz Marin Intl
Tue 6/25
1 stop10h 02m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/22
1 stop16h 58m
San Juan Luis Munoz Marin Intl
Tue 6/25
1 stop11h 50m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Sun 6/23
1 stop11h 42m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 6/25
1 stop6h 32m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
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 stop10h 23m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 7/31
1 stop16h 41m
San Juan Luis Munoz Marin Intl
Wed 8/7
1 stop16h 23m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/26
1 stop17h 41m
San Juan Luis Munoz Marin Intl
Tue 7/2
1 stop10h 02m
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 stop8h 18m
Chicago MidwaySan Juan Luis Munoz Marin Intl
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/2
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Tue 7/9
1 stop22h 21m
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).
Boarding
Comfort
Crew
Overall
Entertainment
Food
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.
Boarding
Comfort
Crew
Overall
Entertainment
Food
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.
Boarding
Comfort
Crew
Overall
Entertainment
Food
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 |
---|---|---|---|---|
Cheapest$119 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$168 | Average$268 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$361 | Average$754 | FlexibilityNo cancel fee | On-timeN/A |
Sunday | 2daily flights |
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Monday | 1daily flight |
Tuesday | 1daily flight |
Wednesday | 1daily flight |
Thursday | 1daily flight |
Friday | 1daily flight |
Saturday | 1daily flight |