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Cheap Flights from Oakland to Chicago $306.8

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Cheapest Flights from Oakland to Chicago (OAK to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Oakland to Chicago (OAK to MDW)

Question : How long are most people's visits to Chicago when they fly in from Oakland?
Answer : Of course you're not most people, but if you were, you'd stay roughly three days.

Question : Are prices changing frequently for this route?
Answer : Prices are fluctuating much more for this route than most. However, the sooner you book, the better price you tend to get.

Question : Is price more important than specific travel days for you?
Answer : The best day to fly on a budget this month is Tuesday. Flexibility is paramount when booking travel plans in order to keep costs down.

Question : In the next four weeks, what day should you book your trip?
Answer : As of January 16th, the cheapest day to fly from Oakland to Chicago is January 27th. Tickets have been sold for 23% below the average price for this route.

Question : How long will the flight typically take from Metropolitan Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)?
Answer : The average flight duration between OAK and MDW is 4 hours and 7 minutes.

Question : Have you considered flying out of an airport besides Metropolitan Oakland International Airport (OAK)?
Answer : Try searching for flights from San Francisco International Airport (SFO) as well. Over the next two months, flights from SFO to MDW are being booked 12% cheaper than flights from OAK to MDW. Being only 12 miles away, it's easily accessible for most.

Question : Which airline has been the most dependable in getting passengers to their destination on schedule?
Answer : The current leader is Southwest Airlines with an 87% on-time rate. Stick to Southwest Airlines and you won't spend more time in airports than you have to. If they are delayed for some reason though, the average delay time is less than 10 minutes.