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Delta flights from Chicago to Oakland, California
Our best Delta deals on Chicago to Oakland, California flight tickets
Spirit Airlines flights from Chicago to Oakland, California
Our best Spirit Airlines deals on Chicago to Oakland, California flight tickets
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How to get the cheapest flight ticket from Chicago to Oakland, California
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Oakland, California?
The month of July is, on average, the cheapest month to fly to Oakland, California from Chicago, with most prices found around $247. If you aren’t able to travel to Oakland, California during the month of July, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $300.
What is the cheapest day to depart on your flight to Oakland, California?
According to our data, Monday is the cheapest day to fly to Oakland, California from Chicago. The lowest ticket price found for a Monday departure recently was $382. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Oakland, California for around $541.
What is the cheapest time of day to depart on your flight to Oakland, California?
At noon is the cheapest time of day to fly from Chicago to Oakland, California when you can find flight prices for as low as $337. Flying to Oakland, California at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $546.
What is the cheapest Chicago to Oakland flight route?
Fly from Chicago Midway to Oakland for the best Chicago - Oakland flight prices
What cabin class options are available on Chicago to Oakland flights?
There are 1 cabin classes available to choose from on Chicago to Oakland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Oakland, California flights?
You could potentially save up to 24% on your flight if you consider stops on a Chicago to Oakland, California flight.
What is the cheapest airline that flies from Chicago to Oakland?
Southwest, Spirit Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to Oakland
What airlines fly to Oakland, California?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Oakland, California from Chicago according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Oakland, California. Keep in mind that there are 9 different airlines that fly to Oakland, California on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Oakland, California on average per day?
1 flights are operational daily from Chicago to Oakland, California as of July 2025. The most popular departure time for this route is 2:00PM, with 62% of flights per day taking off in the afternoon.
How many flights depart from Chicago to Oakland, California on average per week?
As of July 2025, 10 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Chicago to Oakland, California
Cheap Chicago to Oakland, California (CHI to OAK) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Oakland, California
Best Price Found | $53 |
|---|---|
Fastest flight time | 4h 30m |
Direct flights | Every day |
Airports in Oakland, California | 1 airport |
How far is Chicago to Oakland by plane?
Oakland is 1845.3 mi away from Chicago. By plane, this route typically takes 4h 30m.
When did momondo last update prices for flights from Chicago to Oakland Airport?
Prices for flights from Chicago to Oakland Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Oakland Airport?
As of July 2025, there are 3 operators available to choose from for flights from Chicago to Oakland Airport.
How old do you have to be to fly from Chicago to Oakland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Oakland Airport.
What documentation or ID do you need to fly to Oakland Airport?
The travel and health documents required for your trip to Oakland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oakland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Oakland, California?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Oakland, California is Boeing 737 MAX 8, representing 37.88% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 9.09%, Boeing 737-900 Passenger/BBJ3 (winglets) at 9.09%, and Airbus A321neo at 4.55%.
What is the most popular airline from Chicago to Oakland, California?
momondo data reveals that the most frequently booked airline on the route from Chicago to Oakland, California is Southwest, representing 65% of all bookings. The subsequent popular airlines are Spirit Airlines at 17%, Delta at 7%, and Alaska Airlines at 5%.
Best airlines flying from Chicago to Oakland, California
Compare and see reviews for airlines that fly from Chicago to Oakland, California with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $127 | Free Cancellation | Rating 6.3 8,059 reviews | |||
| PriceFrom $238 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $246 | Free Cancellation | Rating 8.0 4,252 reviews |
Southwest Flights From Chicago to Oakland, California
Southwest flies from Chicago to Oakland, California around 10 times per week, with 4,253 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Oakland, California in the last 72 hours was $246 (round-trip), much lower than the average airfare cost of $382 for Southwest flights on this route.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Oakland?
Finding the right flight to Oakland from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Oakland quick and easy, saving you time and money.
Can I find flights from Chicago to Oakland with flexible booking policies on momondo?
momondo does allow users to show only those flights to Oakland from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Oakland?
Once you have performed a search for Chicago to Oakland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Chicago to Oakland right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Oakland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Oakland and let you know when they change.