Oakland (OAK) to Chicago (MDW) flights
One airline flies nonstop from Oakland (OAK) to Chicago (MDW): 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 OAK to MDW
- Southwest AirlinesNot in an allianceWho books it
OAK to MDW 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
OAK to MDW: common questions
Which airlines fly nonstop from OAK to MDW?
Southwest Airlines flies nonstop from Oakland (OAK) to Chicago (MDW).
How far is Oakland from Chicago by plane?
Oakland (OAK) and Chicago (MDW) 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 OAK 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 OAK to MDW with taxes and fees.
Where can I connect between Oakland and Chicago?
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.