Skip to main content
Beginning of main content

Cheap Flights from Oakland to Chicago $274.75

Search over 282,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Guarantee
No Expedia cancellation fee to change or cancel almost any hotel reservation.

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 : From Oakland to Chicago, which day is going to have the most flight times?
Answer : When you're flying from OAK to MDW, the day with the most flight times is Wednesday, with 49 different options. The day with the least number of options is Saturday with 31 different times.

Question : If you're booking OAK to MDW, how many different options of departure times do you have on a daily basis?
Answer : On average, you can expect nine different choices of flight times when you book. The average route has 31 different flight times per day, so expect fewer choices than you're used to.

Question : Is there a preferred airline for getting to Chicago Midway International Airport (MDW) on time?
Answer : NetJets Aviation holds the best record for flights from OAK to MDW with a 100% on-time rate. Hopefully they keep that perfect record alive.

Question : Is there an alternative to Metropolitan Oakland International Airport (OAK) for getting you to Chicago?
Answer : Luckily for you, there is another airport nearby. San Francisco International Airport (SFO) is 12 miles away, and over the next few months, flights are 17% cheaper than those from Metropolitan Oakland International Airport.

Question : How long does it take to get from OAK to MDW?
Answer : If you're able to take the fastest direct flight (which is offered by Southwest Airlines), you can leave OAK at 1:50 PM PST and get to MDW at 7:45 PM CST (3 hours and 55 minutes). Remember, there is a time change of two-hours.

Question : Is price more important than specific travel days for you?
Answer : In December, Wednesday is your lowest-cost day to fly. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.