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Cheap OAK to MDW Flights

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

Chicago

$140.58

Cheap OAK to MDW Flights

Question : Which airline has been the most dependable in getting passengers to their destination on time?
Answer : Southwest Airlines leads the way with an 85% on-time rate. Spend as little time in an airport as necessary by flying with Southwest Airlines. Note that if they do have a delay, it usually lasts about 12 minutes.

Question : When flying into Chicago, is Chicago Midway International Airport your cheapest option?
Answer : Chicago Midway International Airport is a great airport, but there is a cheaper option – O'Hare International Airport. It’s just 16 miles away and flights are being booked 42% cheaper over the coming two months.

Question : Over the coming months, which airline is getting their passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Delta Air Lines is the leader in keeping prices down for their passengers over the next three months. Bookings are being made at just $282, which is quite a deal when compared to the high-end bookings of $889.

Question : Do travelers from Oakland typically stay in Chicago for very long?
Answer : The average time spent in Chicago by travelers from Oakland is five days.

Question : What day has the most flight time options?
Answer : With nine total flight time options, Sunday provides the most flexibility from OAK to MDW. However, with only seven flight times, Thursday doesn't offer quite as many options when finding that perfect departure time.

Question : How much should a trip from Oakland (OAK) to Chicago (MDW) cost?
Answer : Ranging from $282 to $889, prices for OAK to MDW change less than most routes in the United States. However, the sooner you book, the better price you tend to get.

Question : Will you do what it takes to get the absolute lowest-cost flight?
Answer : Friday is your cheapest day to fly in the month of January. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Oakland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Oakland to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with OAK to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Oakland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.