Did you mean Flights from Chicago to Oakland?
Oakland
United StatesOAK
Metropolitan Oakland International Airport
Chicago
United StatesMDW
Chicago Midway International Airport
Metropolitan Oakland International Airport (OAK) serves Oakland; Chicago Midway International Airport (MDW) serves Chicago.
The airports are 1,840 miles apart by great-circle distance.
Roame's current schedule feed shows nonstop service from OAK to MDW.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Published schedule dates span Oct 1, 2026 – Jun 2, 2027.
These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.
Metropolitan Oakland International Airport (OAK) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.
OAK and MDW are approximately 1,840 miles apart by great-circle distance.
Yes. Roame's current schedule feed shows nonstop service from OAK to MDW.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8) and 7S7.
A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.
The award price preview is temporarily unavailable. This does not mean the route is sold out. Use the search controls to check other dates and routes.