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Cheap Flights from Oakland to Chicago (OAK-MDW)
Prices were available within the past 7 days and start at $90 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Frequently asked questions
Travel information
Travel information
Origin airport | Oakland Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta, Southwest Airlines |
Roundtrip price | $216 |
Distance | 1840 mi |
Book with confidence
Book with confidence
The cheapest times to fly from Oakland to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Oakland to Chicago are during the month of June. You can find some of the cheapest flights from Oakland to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Oakland to Chicago
Sunday is one of the best days to book for cheap flights from Oakland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Oakland to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Oakland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Oakland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Oakland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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