Chicago (MDW) to Oakland (OAK) flights
One airline flies nonstop from Chicago (MDW) to Oakland (OAK): Southwest Airlines. The two airports are 1,840 miles (2,961 km) apart. There are also 22 ways to fly it with one stop, through Salt Lake City, Denver and Las Vegas and more.
Airlines flying nonstop from MDW to OAK
- Southwest AirlinesNot in an allianceWho books it
MDW to OAK with one stop
22 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 Las Vegas (LAS)Southwest Airlines the whole way
- Via Boise (BOI)Southwest Airlines the whole way
- Via Albuquerque (ABQ)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
- 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 Spokane (GEG)Southwest Airlines the whole way
- Via Dallas (DAL)Southwest Airlines the whole way
- Via Portland (PDX)Southwest Airlines the whole way
MDW to OAK: common questions
Which airlines fly nonstop from MDW to OAK?
Southwest Airlines flies nonstop from Chicago (MDW) to Oakland (OAK).
How far is Chicago from Oakland by plane?
Chicago (MDW) and Oakland (OAK) are 1,840 miles (2,961 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MDW to OAK 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 OAK with taxes and fees.
Where can I connect between Chicago and Oakland?
The most direct connections are through Salt Lake City (SLC), Denver (DEN), Las Vegas (LAS), Boise (BOI) and Albuquerque (ABQ). On 22 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.