Direct flights from Chicago to Oakland (MDW → OAK)

Distance 2,961 km (1,840 mi)
Est. duration 3h 29m
MDW
Chicago
Chicago Midway International, USA
OAK
Oakland
Metropolitan Oakland International, USA
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Live fares · MDW → OAK

Available flights

Southwest AirlinesNon-stop
from$350
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Frequently asked questions

How far is the flight from Chicago to Oakland? The flight distance from MDW to OAK is approximately 2,961 km (1,840 miles).
How long is the flight from MDW to OAK? The estimated flight time from Chicago to Oakland is approximately 3h 29m.
What airlines fly from MDW to OAK? Airlines operating direct flights from Chicago to Oakland include: WN.

Cheapest fares Chicago → Oakland

Chicago MDW
Oakland OAK
May from $184 June — July — August — September — October —

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for Chicago → Oakland.

Cheap flights from Chicago to Oakland Cheapest month to fly to Oakland Flights from USA Flights to USA Visa-free with USA passport All airports in USA WN routes & destinations All routes by this carrier

Try a nearby airport to Chicago

Flights to Oakland (OAK) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.

ORD → OAK 25 km from MDW Chicago → Oakland USA · 282 destinations SBN → OAK 119 km from MDW South Bend → Oakland USA · 22 destinations RFD → OAK 121 km from MDW Rockford → Oakland USA · 8 destinations MKE → OAK 130 km from MDW Milwaukee → Oakland USA · 34 destinations BMI → OAK 175 km from MDW Bloomington → Oakland USA · 6 destinations

Or try a nearby airport to Oakland

Flights from Chicago (MDW) to other airports within 350 km of Oakland.

MDW → SFO 19 km from OAK Chicago → San Francisco USA · 147 destinations MDW → SJC 46 km from OAK Chicago → San Jose USA · 39 destinations MDW → STS 103 km from OAK Chicago → Santa Rosa USA · 13 destinations MDW → SMF 122 km from OAK Chicago → Sacramento USA · 50 destinations MDW → MRY 129 km from OAK Chicago → Monterey USA · 9 destinations

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →

Other flights from Oakland (OAK)

Albuquerque (ABQ) Austin (AUS) Bellingham (BLI) Boise (BOI) Burbank (BUR) Crescent City (CEC) Dallas (DAL) Denver (DEN) All 34 destinations →