$124 Find Cheap Flights from Chicago Midway Airport to San Juan - Compare and Save

These are the earliest and latest flight times available from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport:

• Earliest: departs at 7:45 am and lands at 12:27 pm
• Latest: departs at 8:55 am and lands at 1:37 pm.

The flight takes about 4h 42m.

Only Economy Class is available on flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport.

A nonstop flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport takes 4h 42m, covering 2,057 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Round-trip flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport range from $303 to $500, with an average of $384 over the past 12 months. Anything below $303 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 11% above the $384 route average. Book 24 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $324 round-trip via Tampa (TPA), compared to $799 for nonstop.

Southwest is the only airline operating Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights. 75% of its flights are on time.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$45 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Airbus A321neo family is used most often on this route, operated mainly by Frontier and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

JetBlue is the only airline on the Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport are currently lower than usual. Average one-way flight prices are about $183, which is 12% below the typical average for this route.

San Juan Luis Munoz Marin Intl Airport (SJU) hosts 5 major car rental companies, with daily rates averaging $41 for economy cars. Top options include:

• Routes Car & Truck Rentals
• U-Save
• Hertz
• Payless
• Europcar

Flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport usually depart from Chicago Midway (MDW) and arrive at San Juan Luis Munoz Marin Intl (SJU).

Morning flights have the fewest delays on this route.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport route, 25% of flights were delayed in the past 3 months, with delays averaging 2h 03m.

One-stop flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport most commonly connect through:

• Orlando (MCO) - 47% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 45% of one-stop connections
• Tampa (TPA) - 3% of one-stop connections
• Baltimore/Washington (BWI) - 2% of one-stop connections

Yes. Flexible dates can save you up to 35% on flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport. Wednesday is the cheapest departure day at $352 round-trip on average, while Saturday is the most expensive at $541, a difference of $189.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only Southwest operates flights between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport.

Flying via Tampa (TPA) gives the shortest average 1-stop total travel time at 6h 53m, compared with 7h 13m via Baltimore/Washington (BWI) and 7h 25m via Lambert-St Louis (STL).

San Juan Luis Munoz Marin Intl Airport is 2 hours ahead of Chicago Midway Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in San Juan Luis Munoz Marin Intl Airport are Viejo San Juan, Puerto Rico Convention Center and Condado Beach. These are among the most viewed places in San Juan Luis Munoz Marin Intl Airport on KAYAK.

Among airlines operating Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• JetBlue: a cabin bag in Economy Class class
• Southwest: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.