ORD - OAK

Flights from Chicago to Oakland from $255 - Compare and Save

This is the cheapest round-trip 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 5/1. 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
$255
Typical prices: $417-$343
Alaska Airlines
Fri 5/1Sun 5/3
ORD - OAK • 1 stop
Cheapest one-way
$128
Typical prices: $126-$249
Alaska Airlines
Tue 5/5
ORD - OAK • 1 stop
Top airlines
Cheapest • from $255 (round-trip)
Best reviews • 8.0 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 • 33% 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

Fri, May 1 - Sun, May 3
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
Alaska Airlines Logo
6:41 am - 1:13 pm
OAK
-
ORD
28h 32m
1 stop
$255Alaska Airlines
Wed, Jun 24 - Tue, Jun 30
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
$257Alaska Airlines
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
Wed, Apr 29 - Wed, May 6
Southwest Logo
11:55 am - 8:20 pm
ORD
-
OAK
10h 25m
2 stops
Southwest Logo
11:10 am - 10:55 pm
OAK
-
ORD
9h 45m
2 stops
$267Southwest
Wed, Apr 29 - Sat, May 2
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
$270Alaska Airlines
Wed, May 6 - Sat, May 9
Southwest Logo
7:45 am - 1:30 pm
ORD
-
OAK
7h 45m
1 stop
Southwest Logo
2:25 pm - 11:25 pm
OAK
-
ORD
7h 00m
1 stop
$271Southwest
Fri, May 1 - Fri, May 8
Alaska Airlines Logo
3:52 pm - 2:38 pm
ORD
-
OAK
24h 46m
1 stop
Alaska Airlines Logo
6:20 am - 4:56 pm
OAK
-
ORD
8h 36m
1 stop
$273Alaska Airlines
Wed, Jun 10 - Tue, Jul 7
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
$274Alaska Airlines
Wed, May 6 - Sat, May 9
Southwest Logo
7:45 am - 3:00 pm
ORD
-
OAK
9h 15m
2 stops
Southwest Logo
5:40 am - 2:20 pm
OAK
-
ORD
6h 40m
1 stop
$276Southwest
Wed, Apr 29 - Sun, May 3
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
Alaska Airlines Logo
6:41 am - 1:13 pm
OAK
-
ORD
28h 32m
1 stop
$279Alaska 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 May.

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$128
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly with an average 33% 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 $128 for a one-way ticket and $255 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 $442 and an overall rating of 8.0, 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.
8.0
SouthwestOverall score based on 4340 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

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

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

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.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The cabin temperature was nice and cool. The wifi was not working.

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Stop changing gates. Stop cancelling flights Stop moving my seat.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

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

Information on your arrival and departure airports