Direct flights from San Jose Cabo to Chicago
All flights from SJD to MDW non-stop. There are direct flights from Los Cabos International, Mexico to Chicago Midway International (MDW), Illinois, USA once a week with Southwest Airlines. The flight distance is 1815 miles and the trip usually takes about 4 hours and 5 minutes.
Airlines with non-stop routes:

Southwest Airlines
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
The timetable & schedule information was updated at 2025-05-15
San Jose Cabo to Chicago flight departures
Select a date to see all scheduled flight departures between SJD to MDW.
SJD - MDW information
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Distance1815 miles (2920 km)
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Flight time4 hours and 5 minutes
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Airlines
Southwest
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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Southwest AircraftBoeing 737 Passenger
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Departure TerminalTerminal 2 (Southwest)
Direct flights from San Jose Cabo to USA

From San Jose Cabo to New York
JFK John F Kennedy International

From San Jose Cabo to New York
EWR Newark Liberty International

From San Jose Cabo to Baltimore
BWI Baltimore Washington International

From San Jose Cabo to Detroit
DTW Detroit Metropolitan Airport

From San Jose Cabo to Seattle
SEA Seattle Tacoma International

From San Jose Cabo to Portland
PDX Portland International

From San Jose Cabo to Charlotte
CLT Charlotte Douglas International

From San Jose Cabo to Chicago
ORD Chicago O Hare International

From San Jose Cabo to Minneapolis
MSP Minneapolis St Paul International

From San Jose Cabo to Atlanta
ATL Hartsfield–Jackson Atlanta International Airport