$133 Cheap flights from Oakland Intl. to Midway Intl. (OAK to MDW)

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Oakland Intl. to Midway Intl.

Amazing OAK to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $266 round trip and $133 one way. Prices and availability subject to change. Additional terms may apply.

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Swissotel - Chicago
Aloft Chicago Downtown River North
Virgin Hotels Chicago
Hilton Chicago
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Traveling From
Oakland Intl.
Traveling To
Midway Intl.
Shortest Flight Time
8 hours 5 mins
Earliest Departure Time
5:10AM CST
Latest Departure Time
8:50AM CST
Lowest Flight Price
$266

Route Info

Flight path for flights from Metropolitan Oakland International Airport to Chicago Midway International Airport.


Distance:
1,850.00 miles


Discover our best flights from Oakland OAK to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Oakland OAK to Chicago MDW at the right price  

Airfares to Chicago MDW from Oakland OAK currently cost between $266 and $395. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Oakland OAK to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Oakland OAK to Chicago MDW on Travelocity starting at $133. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Oakland OAK quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from OAK to take around 8 hour(s) 5 min(s).  

 

Find our cheapest airfares for flights from Oakland OAK to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from OAK. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Oakland OAK to Chicago MDW today 

If you’re flexible about when you travel, February is usually the cheapest month to fly from Oakland OAK to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Oakland OAK 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from OAK have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Oakland OAK with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.