Stay in Chicago
Booking.com
Hotels, apartments and guesthouses — many with free cancellation.
Find a stay on Booking.com (partner link)Oakland to Chicago
Oakland San Francisco Bay Airport (OAK) to Chicago Midway International Airport (MDW)
The essentials
Straight-line distance2,961 km1,840 miles · great-circle
Estimated flight time3h 42mAt 800 km/h cruise. Scheduled times run longer.
Direct flights? Yes 2 airlines in our data
Time difference +2 hours Chicago is 2 hours ahead of Oakland (UTC−7 → UTC−5)
Airlines listed on OAK → MDW
- FL AirTran Airways
- WN Southwest Airlines
Route map
Weather: Oakland vs Chicago
Oakland OAK
Chicago MDW
Money: USD ↔ USD
Both ends use the same currency (USD). Open the converter for other pairs.
Partner Compare OAK → MDW flights
Compare flights on KAYAK
See current fares and schedules for OAK → MDW across airlines and booking sites. Search OAK to MDW on KAYAK.
Data on arrival
Airalo
Land in United States with mobile data already set up.
Get an eSIM on Airalo (partner link)