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Cheap flights from Oakland (OAK) to Chicago (ORD)
Prices were available within the past 7 days and start at $42 for one-way flights and $85 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Travel information
Travel information
Origin airport | Oakland Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | Alaska Airlines, Delta, Spirit Airlines |
Roundtrip price | $85 |
Distance | 1831 mi |
Book with confidence
Book with confidence
Oakland to Chicago Flights
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 October. 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 2024. You can also book with separate airlines for your outbound and return journeys, from $42 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.
Frequently asked questions
Frequently asked questions
Frequently asked questions
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Top Routes from Oakland
- Oakland to San Diego (OAK - SAN)
- Oakland to Mexico City (OAK - MEX)
- Oakland to Newark Liberty Intl. Airport (OAK - EWR)
- Oakland to Los Angeles (OAK - LAX)
- Oakland to Honolulu (OAK - HNL)
- Oakland to Orange County (OAK - SNA)
- Oakland to New York (OAK - LGA)
- Oakland to Lihue (OAK - LIH)
- Oakland to Seattle (OAK - SEA)
- Oakland to Guadalajara (OAK - GDL)
- Oakland to Kahului (OAK - OGG)
- Oakland to New York (OAK - JFK)
Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
- Phoenix to Chicago (PHX - ORD)
- Los Angeles to Chicago (LAX - ORD)
- Miami to Chicago (MIA - ORD)
- Tampa to Chicago (TPA - ORD)
- New York to Chicago (LGA - ORD)
- Boston to Chicago (BOS - ORD)
- Fort Lauderdale to Chicago (FLL - ORD)
- Minneapolis to Chicago (MSP - ORD)
- Denver to Chicago (DEN - ORD)
- New York to Chicago (JFK - ORD)
- Seattle to Chicago (SEA - ORD)
Top Routes from Oakland
- Alaska Airlines Oakland to San Diego
- Volaris Oakland to Mexico City
- Spirit Airlines Oakland to Newark Liberty Intl. Airport
- Alaska Airlines Oakland to Honolulu
- Alaska Airlines Oakland to Orange County
- Spirit Airlines Oakland to New York
- Alaska Airlines Oakland to Lihue
- Alaska Airlines Oakland to Seattle
- Volaris Oakland to Guadalajara
- Alaska Airlines Oakland to Kahului
Top Routes to Chicago
- Frontier Airlines Phoenix to Chicago
- Alaska Airlines Los Angeles to Chicago
- American Airlines Miami to Chicago
- JetBlue Airways Tampa to Chicago
- Spirit Airlines New York to Chicago
- JetBlue Airways Boston to Chicago
- JetBlue Airways Fort Lauderdale to Chicago
- Delta Minneapolis to Chicago
- Frontier Airlines Denver to Chicago
- JetBlue Airways New York to Chicago
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Main Airports for Flights
- San Francisco Intl. Airport (SFO)
- San Carlos Airport (SQL)
- Buchanan Field Airport (CCR)
- Norman Y. Mineta San Jose Intl. Airport (SJC)
- Stockton Municipal Airport (SCK)
- Watsonville Municipal Airport (WVI)
- Sonoma County Airport (STS)
- Modesto City - County Airport (MOD)
- Sacramento Intl. Airport (SMF)
- Salinas Municipal Airport (SNS)