San Jose (SJC) to Chicago (MDW) flights
One airline flies nonstop from San Jose (SJC) to Chicago (MDW): Southwest Airlines. The two airports are 1,834 miles (2,951 km) apart. There are also 29 ways to fly it with one stop, through Salt Lake City, Denver and Reno and more.
Airlines flying nonstop from SJC to MDW
- Southwest AirlinesNot in an allianceWho books it
SJC to MDW with one stop
29 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Salt Lake City (SLC)Southwest Airlines the whole way
- Via Denver (DEN)Southwest Airlines the whole way
- Via Reno (RNO)Southwest Airlines the whole way
- Via Las Vegas (LAS)Southwest Airlines the whole way
+1
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Boise (BOI)Southwest Airlines the whole way
- Via Burbank (BUR)Southwest Airlines the whole way
- Via Ontario (ONT)Southwest Airlines the whole way
- Via Palm Springs (PSP)Southwest Airlines the whole way
- Via Los Angeles (LAX)Southwest Airlines the whole way+1
- Via Phoenix (PHX)Southwest Airlines the whole way
- Via Long Beach (LGB)Southwest Airlines the whole way
- Via San Diego (SAN)Southwest Airlines the whole way
- Via Dallas (DFW)American Airlines, then Frontier Airlines
- Via Dallas (DAL)Southwest Airlines the whole way
SJC to MDW: common questions
Which airlines fly nonstop from SJC to MDW?
Southwest Airlines flies nonstop from San Jose (SJC) to Chicago (MDW).
How far is San Jose from Chicago by plane?
San Jose (SJC) and Chicago (MDW) are 1,834 miles (2,951 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does SJC to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for SJC to MDW with taxes and fees.
Where can I connect between San Jose and Chicago?
The most direct connections are through Salt Lake City (SLC), Denver (DEN), Reno (RNO), Las Vegas (LAS) and Minneapolis (MSP). On 27 of them the same airline flies both flights, for example Southwest Airlines through Salt Lake City.
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.