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Direct flights from San Juan to Chicago

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San Juan

Puerto Rico

Puerto Rico

SJU

Luis Muñoz Marín International Airport

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Chicago

United States

United States

MDW

Midway International Airport

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Flight schedule
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Click to show full flight schedule

Distance
2,059 miles  ·  (3,314 km)
Flight time
5 hours and 20 minutes
Airlines
  • Southwest Airlines
Alliances
  • OneWorld
  • SkyTeam
  • Star Alliance
Classes
  • Economy
  • Premium Economy
  • Business Class
  • First Class
Aircrafts
  • Boeing 737-700 (winglets)

San Juan to Chicago Flight Schedule

Scan through all non-stop flights from San Juan to Chicago. The full flight schedule below gives an overview of all non-stop flights from SJU to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.

First SJU-MDW flights start in November

Note: for airline-specific flight schedules, please scroll further down.

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Airlines flying from San Juan to Chicago

Airline-specific flight schedules from San Juan to Chicago

Currently, there is only one airline operating non-stop flights from San Juan SJU to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.

Click an airline below to view their SJU MDW flight schedule.

Southwest Airlines
Southwest Airlines flight schedulefrom San Juan to Chicago

Southwest Airlines flights start in November
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San Juan to Chicago Flights

Flights from SJU to MDW are operated twice a week. Departure times vary between 14:55 - 16:40. The earliest flight departs at 14:55, the last flight departs at 16:40. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.

On this non-stop route, you can fly in Economy only.

The fastest direct flight from San Juan to Chicago takes 5 hours and 20 minutes. The flight distance between San Juan and Chicago is 2,059 miles (or 3,314 km).

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Frequently asked questions - FAQ

How many airports are there in Chicago?

There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (formerly Orchard Depot Fi (ORD).

How many flights per week are there from SJU to MDW?

There are 2 flights per week flying from San Juan to Chicago (as of October 2020).

How long does it take to fly from San Juan to Chicago?

5 hours and 20 minutes is the average flight time from San Juan to Chicago.

How far is Chicago from San Juan?

The distance from San Juan to Chicago is 2,059 miles (3,314 kilometers).

What airlines fly nonstop from SJU airport to MDW airport?

Southwest Airlines is the only airline flying nonstop from San Juan to Chicago.

What alliances have direct flights from San Juan to Chicago?

There are no alliances flying direct from San Juan to Chicago at the moment.

What classes are available from San Juan to Chicago?

You can fly non-stop in Economy only.

What aircraft types fly from San Juan to Chicago?

Aircraft types that fly from San Juan to Chicago:

  • Boeing 737-700 (winglets)

What is the earliest flight departing from San Juan to Chicago?

The earliest flight departs at 14:55 from San Juan and arrives at 18:15 at Chicago.

What is the latest flight available from San Juan to Chicago?

The latest flight departs at 16:40 from San Juan and arrives at 20:00 at Chicago.

Non-stop flights from SJU to MDW

2,059 miles (3,314 km)  ·  5h 20m

Round trip
1 passenger
Economy
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Return schedule
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  • Depart
  • Arrive
  • Airline
  • Flight no
  • Aircraft
  • Classes
  • 15:10

  • 18:30

  • Southwest Airlines

    Southwest Airlines

  • WN 3898

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

  • 16:15

  • 19:35

  • Southwest Airlines

    Southwest Airlines

  • WN 1780

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

  • 16:40

  • 20:00

  • Southwest Airlines

    Southwest Airlines

  • WN 3449

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

  • 16:40

  • 20:00

  • Southwest Airlines

    Southwest Airlines

  • WN 1038

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

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