Direct flights from Chicago to San Jose Cabo

Airlines Schedules

MDW - SJD route map All flights from MDW to SJD non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Los Cabos International (SJD), Mexico with Southwest Airlines. 8 weekly departures are currently scheduled on this route. Departure times range from 08:50 to 10:10 depending on the schedule period. The flight distance is 1815 miles (2920 km). Flight time ranges from 4 hours and 40 minutes to 4 hours and 45 minutes.

MDW
Chicago Midway

Chicago , USA

SJD
Los Cabos

San Jose Cabo , Mexico

MDW

Chicago Midway
USA

Chicago , USA

Los Cabos

San Jose Cabo , Mexico

SJD

Flight time 4h 40min to 4h 45min

Updated Aug 24, 2026

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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 08:50 and 10:10

Sun

Mon

Tue

Wed

Thu

Fri

Sat

From Mar 2027

Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS

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Flight schedule from Chicago to San Jose Cabo 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

Tue

Mar 9

Wed

Mar 10

Thu

Mar 11

Fri

Mar 12

Sat

Mar 13

Sun

Mar 14

WN3636

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10:10

08:50

08:55

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

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Chicago to San Jose Cabo scheduled departures

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

Select date to show departures:

Wednesday

Wed

Sep 23

0 flights(0)

Thursday

Thu

Sep 24

0 flights(0)

Friday

Fri

Sep 25

0 flights(0)

Saturday

Sat

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)

Time

Airline

Flight

No flights found.

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

Chicago - San Jose Cabo direct flight map

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MDW - SJD route facts

Distance

1815 miles (2920 km)
Flight time

4 hours and 40 minutes to 4 hours and 45 minutes
Airline

Southwest
Airline alliances

Low-cost carrier
Cabins

Economy
Arrival terminals

Terminal 2
Aircraft

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

Route FAQ

Southwest Airlines operates non-stop flights from MDW to SJD with 8 weekly departures.

Scheduled flight time from MDW to SJD ranges from 4 hours and 40 minutes to 4 hours and 45 minutes. The route covers 1815 miles (2920 km).

8 weekly departures are currently scheduled on this route, with published departure times ranging from 08:50 to 10:10 depending on the schedule period.

Arrival terminal: Terminal 2.

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