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Your flight ticket price will generally be cheaper if you fly to.

Find our best return flights from Oakland OAK to Chicago MDW at the right price. Airfares to Chicago MDW from Oakland OAK currently cost betweenandIt’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Oakland (OAK) to Chicago (MDW) Flights from Oakland (OAK) to Chicago (MDW) Book flights from Oakland to Chicago (Midway) with Southwest Airlines . It’s easy to find the Oakland International Airport to Chicago Midway International Airport flight to make your booking and travel a breeze.

Cons: No beverage service.

The total flight duration time from Oakland (OAK) to Chicago (MDW) is typically 9 hours 50 minutes. This is the average non-stop flight time based upon historical flights for this route. During this period travelers can expect to fly about 2, miles, or 3, kilometers.

Prices were available within the past 7 days and starts atfor one-way flights andfor round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals.

Ups and downs.

One way. Roundtrip. Tue, Oct OAK. Oakland. Find flights to Chicago Midway Airport fromFly from Oakland on Allegiant Air, Delta, Volaris and more. Search for Chicago Midway Airport flights on. Apr 28, Delta Flights from Oakland to Chicago (OAK to MDW) starting atAs COVID disrupts travel, a few airlines are offering WAIVING CHANGE FEE for new bookings.