$113 Find Cheap Flights from San Juan to Chicago Midway Airport - Compare and Save

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

• Earliest: departs at 1:30 pm and lands at 6:31 pm
• Latest: departs at 3:30 pm and lands at 8:31 pm.

The flight takes about 5h 01m.

Two cabin classes are available on flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport:

• Economy Class
• First Class

A nonstop flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport takes 5h 01m, 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport range from $291 to $464, with an average of $342 over the past 12 months. Anything below $291 counts as a good deal.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 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 Delta. Other aircraft seen on the route include Boeing 737-800 variants.

One-way fares from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $116, which is 52% below the typical average for this route.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

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

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

• Atlanta Hartsfield-Jackson (ATL) - 48% of one-stop connections
• Orlando (MCO) - 38% of one-stop connections
• Baltimore/Washington (BWI) - 7% of one-stop connections
• Tampa (TPA) - 5% of one-stop connections

Yes. Flexible dates can save you up to 33% on flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport. Thursday is the cheapest departure day at $316 round-trip on average, while Wednesday is the most expensive at $466, a difference of $150.

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 San Juan Luis Munoz Marin Intl Airport and Chicago Midway Airport.

Flying via Tampa (TPA) gives the shortest average 1-stop total travel time at 7h 14m, compared with 7h 45m via Atlanta Hartsfield-Jackson (ATL) and 7h 45m via Fort Lauderdale (FLL).

Chicago Midway Airport is 1 hour behind San Juan Luis Munoz Marin Intl Airport (Central Time vs Atlantic Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

• 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.