OAK - ORD

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

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to O'Hare Intl departing on 6/2. 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 Chicago O'Hare Intl Airport

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

Cheapest round-trip
$311
Typical prices: $425-$287
Delta
Wed 5/27Mon 6/1
OAK - ORD • 1 stop
Cheapest one-way
$129
Typical prices: $114-$222
Delta
Tue 6/2
OAK - ORD • 1 stop
Top airlines
Cheapest • from $311 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Oakland and O'Hare Intl. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $236 (round-trip)
Shortest trip • 6h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 41% 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 O'Hare Intl!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to O'Hare Intl 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 Oakland to O'Hare Intl

Wed, May 27 - Mon, Jun 1
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
3:47 pm - 11:57 pm
ORD
-
OAK
10h 10m
2 stops
$311Delta
Sat, May 30 - Tue, Jun 2
Alaska Airlines Logo
2:58 pm - 11:55 pm
OAK
-
ORD
6h 57m
1 stop
Alaska Airlines Logo
9:00 am - 2:14 pm
ORD
-
OAK
7h 14m
1 stop
$313Alaska Airlines
Fri, May 29 - Tue, Jun 9
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:37 pm - 11:54 pm
ORD
-
OAK
6h 17m
1 stop
$315Delta
Wed, May 27 - Mon, Jun 1
Southwest Logo
1:50 pm - 10:55 pm
OAK
-
ORD
7h 05m
1 stop
Southwest Logo
4:50 pm - 11:55 pm
ORD
-
OAK
9h 05m
1 stop
$316Southwest
Tue, Jun 2 - Tue, Jun 9
Delta Logo
6:00 am - 8:14 pm
OAK
-
ORD
12h 14m
2 stops
Delta Logo
2:07 pm - 11:54 pm
ORD
-
OAK
11h 47m
2 stops
$318Delta
Thu, May 28 - Tue, Jun 2
Southwest Logo
12:10 pm - 10:55 pm
OAK
-
ORD
8h 45m
2 stops
Southwest Logo
4:50 pm - 10:35 pm
ORD
-
OAK
7h 45m
1 stop
$320Southwest
Thu, May 28 - Tue, Jun 2
Southwest Logo
12:10 pm - 10:55 pm
OAK
-
ORD
8h 45m
2 stops
Southwest Logo
10:30 am - 6:15 pm
ORD
-
OAK
9h 45m
2 stops
$325Southwest
Fri, Jun 5 - Mon, Jun 8
Alaska Airlines Logo
6:02 am - 6:50 pm
OAK
-
ORD
10h 48m
1 stop
Alaska Airlines Logo
7:59 pm - 9:45 am
ORD
-
OAK
15h 46m
1 stop
$329Alaska Airlines
Thu, May 28 - Mon, Jun 1
Southwest Logo
8:25 am - 6:35 pm
OAK
-
ORD
8h 10m
2 stops
Southwest Logo
7:20 pm - 12:05 am
ORD
-
OAK
6h 45m
1 stop
$334Southwest
Wed, Jun 17 - Wed, Jun 24
Alaska Airlines Logo
10:37 am - 11:36 pm
OAK
-
ORD
10h 59m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$335Alaska Airlines
Booking Insights

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

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Chicago O'Hare Intl Airport, 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 Oakland to Chicago O'Hare Intl Airport is July, where tickets cost $232 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $527 and $514 respectively.

Good to know

Low seasonMarch
Cheapest flight$129
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Oakland to Chicago O'Hare Airport

When to book flights from Oakland to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Oakland to O'Hare Intl 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 Oakland to Chicago O'Hare Airport flights

  • Can I rent a car at ORD?

    Alamo, Avis, Budget, Dollar, Enterprise, Hertz, and SIXT are some of the top car rentals that serve ORD. Although none have counters at the airport, they offer their own round-the-clock shuttle service that pick up their passengers at outside of baggage claim on the Arrivals lower level.

  • Where can I receive emergency assistance at ORD?

    If you require emergency housing or transport assistance, you should head to one of Traveler’s Aid’s offices. Traveler’s Aid is a non-profit organization catering to distressed or stranded passengers. At ORD, it has offices in Terminals 1, 2, 3, and 5.

  • Can I breastfeed my baby at OAK?

    You can comfortably breastfeed your baby at OAK, as it features free-standing Mamava suites throughout the airport. Each lactation pod has a fold-down table, a collapsible table, a power outlet, and two benches.

  • Where can I spot art at OAK?

    If you’re an art enthusiast, while waiting for your flight to ORD at OAK, you should visit the baggage claim of Terminal 2 and the airside of Terminal 3. At either, you’ll get to see several pieces of artwork made by local artists.

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

    In the last 3 days, the lowest price for a flight from Oakland to Chicago O'Hare Intl Airport was $129 for a one-way ticket and $311 for a round-trip.

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

    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 Oakland to Chicago O'Hare Airport?

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

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

    Star Alliance, and oneworld are the airline alliances operating flights between Oakland and Chicago O'Hare Airport, with Star Alliance being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Oakland to Chicago are Southwest and Alaska Airlines. With an average price for the route of $377 and an overall rating of 7.9, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $522 and an overall rating of 7.9.

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

    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 Oakland to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Oakland 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 Oakland to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Oakland with another airline. Booking your flights between Oakland and ORD 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 Oakland to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Oakland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Oakland to Chicago O'Hare Intl Airport

  • When traveling to Chicago O’Hare International Airport (ORD) from OAK, we suggest arriving at the airport about 2 hours before your scheduled departure time. This will allow you to check your luggage, pass through security checkpoints, find your gate, and maybe even grab a bite to eat before you take off.
  • While waiting for your flight to ORD, you can relax at OAK’s Escape Lounge. Situated between gates 8 and 8A in Terminal 1, this lounge features premium food, snacks, a television, printers, copiers, and a flight information monitor. Daily, it operates from 4:30 am to 9 pm.
  • ORD is the main international airport serving Illinois’ most populous city, Chicago. It is situated approximately 17 miles northwest of the Loop business district. As of today, this airport serves as a hub for United and American Airlines. Additionally, it serves as a focus city for Spirit Airlines and Polar Air Cargo.
  • If you’d like to stay at a hotel within ORD’s grounds, you’re in luck, as this airport is home to an on-site hotel, the Hilton Chicago O’Hare Airport Hotel. This hotel is located opposite Terminal 2 and connected to ORD’s domestic terminals through an underground walkway.
  • There are various means of public transportation that you can rely on to travel from ORD to your preferred destination in Chicago. If the destination you’re headed to is near one of the commuter train stations in Chicago, you should board a Metra train. On the other hand, if the destination you intend to get to is a bit distant from the stations, it’s in your best interest to board a taxi. You’ll have to head to the airport’s Metra station across from the Multi-Modal Facility to access a Metra train, while to access a taxi, you'll have to get to the curb front on the lower level of your terminal.

Reviews of the top 4 airlines serving from Oakland to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Chicago. 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 Oakland to O'Hare Intl? 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
Alaska AirlinesOverall score based on 12331 reviews
7.8Comfort
8.1Boarding
7.0Food
8.5Crew
7.0Entertainment
Airline reviews

I had to cancel my trip due to medical reasons. I have been unable to cancel online through either Kayak or Alaska Airlines.. I am trying to get my insured trip reimbursed by XCover. They are requiring a notice of cancellation or not using to get my refund. Please help me get that information. I have been unable to get this information from either Kayak or Alaska Airlines.

2.0 MediocreDave, May 2026
PSP - SEA
Read more Alaska Airlines reviews

I had to cancel my trip due to medical reasons. I have been unable to cancel online through either Kayak or Alaska Airlines.. I am trying to get my insured trip reimbursed by XCover. They are requiring a notice of cancellation or not using to get my refund. Please help me get that information. I have been unable to get this information from either Kayak or Alaska Airlines.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

Agent could not provide me a boarding pass for the second leg of my flights - yet with a partner airline. Not understood.

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

No headphones provided. No gf food. Only 1 beverage cart run sAN to HNL. Rarely saw crew members

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

Shut down without prior notice End up with spending lots of extra $$$

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

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

Information on your arrival and departure airports