Southwest Airlines
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Mexico
Los Cabos International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from San José del Cabo to Chicago. The full flight schedule below gives an overview of all non-stop flights from SJD to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from San José del Cabo SJD 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 SJD MDW flight schedule.
Flights from SJD to MDW are operated once a week. Departure times vary between 11:15 - 13:20. The earliest flight departs at 11:15, the last flight departs at 13:20. 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 José del Cabo to Chicago takes 3 hours and 55 minutes. The flight distance between San José del Cabo and Chicago is 1,804 miles (or 2,903 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There is 1 flight per week flying from San José del Cabo to Chicago (as of April 2026).
3 hours and 55 minutes is the average flight time from San José del Cabo to Chicago.
The distance from San José del Cabo to Chicago is 1,804 miles (2,903 kilometers).
Southwest Airlines is the only airline flying nonstop from San José del Cabo to Chicago.
There are no alliances flying direct from San José del Cabo to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from San José del Cabo to Chicago:
The earliest flight departs at 11:15 from San José del Cabo and arrives at 17:10 at Chicago.
The latest flight departs at 13:20 from San José del Cabo and arrives at 19:15 at Chicago.
1,804 miles (2,903 km) · 3h 55m
11:15
17:10
Southwest Airlines
WN 3637
Southwest Airlines
Boeing 757
Y
W
J
F
11:35
17:35
Southwest Airlines
WN 3637
Southwest Airlines
Boeing 757
Y
W
J
F
11:55
17:55
Southwest Airlines
WN 3637
Southwest Airlines
Boeing 757
Y
W
J
F
13:20
19:15
Southwest Airlines
WN 3637
Southwest Airlines
Boeing 757
Y
W
J
F
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