ORD - OAK

$129 Find Cheap Flights from Chicago O'Hare Airport to Oakland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Oakland departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Oakland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$257
Typical prices: $485-$246
Delta
Wed 6/3Wed 6/17
ORD - OAK • 1 stop
Cheapest one-way
$129
Typical prices: $126-$249
Delta
Wed 5/27
ORD - OAK • 1 stop
Top airlines
Cheapest • from $257 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between O'Hare Intl and Oakland. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $334 (round-trip)
Shortest trip • 6h 36m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 34% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Oakland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from O'Hare Intl to Oakland (ORD-OAK)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Oakland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Oakland

Wed, Jun 3 - Wed, Jun 17
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
Delta Logo
12:33 pm - 9:57 pm
OAK
-
ORD
7h 24m
1 stop
$257Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:19 pm - 11:57 pm
ORD
-
OAK
8h 38m
2 stops
Delta Logo
12:33 pm - 9:57 pm
OAK
-
ORD
7h 24m
1 stop
$262Delta
Mon, Jun 1 - Wed, Jun 3
Alaska Airlines Logo
7:49 pm - 9:55 am
ORD
-
OAK
16h 06m
1 stop
Alaska Airlines Logo
6:02 am - 6:50 pm
OAK
-
ORD
10h 48m
1 stop
$271Alaska Airlines
Thu, Jun 4 - Mon, Jun 8
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
Alaska Airlines Logo
2:58 pm - 11:55 pm
OAK
-
ORD
6h 57m
1 stop
$285Alaska Airlines
Sat, May 23 - Sat, May 30
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
Alaska Airlines Logo
2:58 pm - 11:55 pm
OAK
-
ORD
6h 57m
1 stop
$298Alaska Airlines
Wed, May 27 - Tue, Jun 2
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
Alaska Airlines Logo
10:29 am - 6:50 pm
OAK
-
ORD
6h 21m
1 stop
$299Alaska Airlines
Wed, Jun 3 - Wed, Jun 10
Alaska Airlines Logo
2:10 pm - 11:50 pm
ORD
-
OAK
11h 40m
1 stop
Alaska Airlines Logo
8:10 pm - 1:21 pm
OAK
-
ORD
15h 11m
1 stop
$302Alaska Airlines
Wed, Jun 24 - Sat, Jul 4
Delta Logo
7:37 pm - 11:54 pm
ORD
-
OAK
6h 17m
1 stop
Delta Logo
12:33 pm - 9:23 pm
OAK
-
ORD
6h 50m
1 stop
$306Delta
Sat, Jun 6 - Tue, Jun 16
Delta Logo
1:44 pm - 10:34 pm
ORD
-
OAK
10h 50m
2 stops
Delta Logo
12:33 pm - 9:57 pm
OAK
-
ORD
7h 24m
1 stop
$311Delta
Sat, May 23 - Wed, May 27
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
Alaska Airlines Logo
10:29 am - 6:50 pm
OAK
-
ORD
6h 21m
1 stop
$313Alaska Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Oakland flights

Get data-powered insights and trends into flights from O'Hare Intl to Oakland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Oakland, California?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Oakland, California departing in June.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Oakland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Oakland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Oakland is September, where tickets cost $251 (return) on average. On the other hand, the most expensive months are February and August, where the average cost of round-trip tickets is $548 and $503 respectively.

Good to know

Low seasonFebruary
Cheapest flight$129
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago O'Hare Airport to Oakland

When to book flights from O'Hare Intl to Oakland

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Oakland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Oakland flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Oakland?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Oakland was $129 for a one-way ticket and $257 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Oakland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Oakland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Oakland?

    SkyTeam is the only airline alliance operating flights between Chicago O'Hare Airport and Oakland.

  • Which is the best airline for flights from Chicago to Oakland, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and Delta. With an average price for the route of $458 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $355 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Oakland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Oakland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Oakland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Oakland from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Oakland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Oakland with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and OAK can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Oakland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Oakland from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from O'Hare Intl to Oakland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oakland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Oakland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4307 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Very easy to use and convenient, you can perform any action within the same portal

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Everything you need to know for your flight from O'Hare Intl to Oakland

Information on your arrival and departure airports