Cheap flights from Chicago to Oakland
1,840 mi · 45m average nonstop
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Quick answer: Chicago to Oakland at a glance
Cheap flights from Chicago (MDW) to Oakland (OAK) cover 1,840 miles (2,960 km) in about 45m nonstop, with 2 airlines flying direct — a long-haul international route. Search Kayak for today's cheapest live fare. Route difficulty 5/10.
Summary computed from real OpenFlights coordinates — not an estimate. Prices update live on Kayak.
Flying from Chicago to Oakland covers 1,840 miles (2,961 km) in approximately 0 hour 45 minutes. 2 airlines offer direct flights on this long-haul international route. This is a long-haul international route requiring advance planning for connections and layovers.
Nonstop distance 1,840 miles. Direct carriers include FL and WN.
We don't track historical prices for this route yet. Search live fares on Kayak for today's best price across 100+ airlines and booking sites.
Airlines on this route
2 airlines fly Chicago → Oakland. All are direct routes.
| Airline | Route type |
|---|---|
| FL | Direct |
| WN | Direct |
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Chicago to Oakland — quick answers
How far is Chicago from Oakland by plane?
The nonstop flight distance from Chicago (MDW) to Oakland (OAK) is 1,840 miles (2,960 km), calculated as a great-circle line from published OpenFlights airport coordinates. Actual flown distance is slightly longer due to airways and winds.
How long is the flight from Chicago to Oakland?
The average nonstop flight time from MDW to OAK is 45 minutes. Gate-to-gate time is usually 20–35 minutes longer; connecting itineraries add 1–4 hours depending on the layover.
Which airlines fly from Chicago to Oakland?
2 airlines serve this route nonstop: FL, WN. Schedules and amenities differ by carrier — compare live frequencies and fare classes on Kayak before you book.