Chicago (MDW) to San Jose Cabo (SJD) flights
One airline flies nonstop from Chicago (MDW) to San Jose Cabo (SJD): Southwest Airlines. The two airports are 1,805 miles (2,905 km) apart. There are also 26 ways to fly it with one stop, through Saint Louis, Dallas and Kansas City and more.
Airlines flying nonstop from MDW to SJD
- Southwest AirlinesNot in an allianceWho books it
MDW to SJD with one stop
26 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Dallas (DFW)Frontier Airlines, then American Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Austin (AUS)Southwest Airlines the whole way
- Via Houston (HOU)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Denver (DEN)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Phoenix (PHX)Southwest Airlines the whole way
- Via Guadalajara (GDL)Volaris the whole way
- Via Leon/Guanajuato (BJX)Volaris the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Las Vegas (LAS)Southwest Airlines the whole way
MDW to SJD: common questions
Which airlines fly nonstop from MDW to SJD?
Southwest Airlines flies nonstop from Chicago (MDW) to San Jose Cabo (SJD).
How far is Chicago from San Jose Cabo by plane?
Chicago (MDW) and San Jose Cabo (SJD) are 1,805 miles (2,905 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MDW to SJD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to SJD with taxes and fees.
Where can I connect between Chicago and San Jose Cabo?
The most direct connections are through Saint Louis (STL), Dallas (DFW), Kansas City (MCI), Austin (AUS) and Houston (HOU). On 17 of them the same airline flies both flights, for example Southwest Airlines through Saint Louis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.