Direct flights from San Jose Cabo to Chicago

Airlines Schedules

SJD - MDW route map All flights from SJD to MDW non-stop. There are direct flights from Los Cabos International (SJD), Mexico to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 7 weekly departures are currently scheduled on this route. Departure times range from 11:50 to 13:35 depending on the schedule period. The flight distance is 1815 miles (2920 km). Flight time is about 4 hours and 10 minutes.

SJD
Los Cabos

San Jose Cabo , Mexico

MDW
Chicago Midway

Chicago , USA

SJD

Los Cabos

San Jose Cabo , Mexico

Chicago Midway
USA

Chicago , USA

MDW

Flight time 4h 10min

Updated Aug 24, 2026

CHANGE DIRECTION

Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 11:50 and 13:35 • From Terminal 2

Sun

Mon

Tue

Wed

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Sat

From Mar 2027

Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS

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Flight schedule from San Jose Cabo to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

Flight

Mon

Mar 8

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Mar 9

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Mar 10

Thu

Mar 11

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Mar 12

Sat

Mar 13

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Mar 14

WN3637

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13:35

12:50

12:20

The timetable & schedule information was updated at 2026-08-24

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San Jose Cabo to Chicago scheduled departures

Select a date to see every published non-stop departure between SJD and MDW.

Select date to show departures:

Thursday

Thu

Sep 24

0 flights(0)

Friday

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Sep 25

0 flights(0)

Saturday

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Sep 26

0 flights(0)

Sunday

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Sep 27

0 flights(0)

Monday

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Sep 28

0 flights(0)

Tuesday

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Sep 29

0 flights(0)

Wednesday

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Sep 30

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Flight

No flights found.

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Route map from San Jose Cabo, SJD to Chicago, MDW. The distance is 1815 miles or 2920 km.

San Jose Cabo - Chicago direct flight map

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SJD - MDW route facts

Distance

1815 miles (2920 km)
Flight time

4 hours and 10 minutes
Airline

Southwest
Airline alliances

Low-cost carrier
Cabins

Economy
Departure terminals

Terminal 2
Aircraft

Boeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from SJD to MDW with 7 weekly departures.

Scheduled flight time from SJD to MDW is 4 hours and 10 minutes. The route covers 1815 miles (2920 km).

7 weekly departures are currently scheduled on this route, with published departure times ranging from 11:50 to 13:35 depending on the schedule period.

Departure terminal: Terminal 2.

Economy are currently scheduled on non-stop flights for this route.