Direct flights from Oakland to Chicago (OAK → MDW)

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

Available flights

Southwest AirlinesNon-stop
from$201
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Frequently asked questions

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

Cheapest fares Oakland → Chicago

Oakland OAK
Chicago MDW
May from $275 June from $174 July from $183 August — September — October —

Related guides for this route

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

Cheap flights from Oakland to Chicago Cheapest month to fly to Chicago 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 Oakland

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

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

Or try a nearby airport to Chicago

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

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

Other flights from Chicago (MDW)

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