OAK - ORD

$156 Find Cheap Flights from Oakland to Chicago O'Hare Airport - Compare and Save

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 9/30. 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
$352
Typical prices: $234-$388
Alaska Airlines, Frontier
Tue 7/21Mon 9/21
OAK - ORD • 1 stop
Cheapest one-way
$156
Typical prices: $155-$232
Frontier
Wed 9/30
OAK - ORD • 1 stop
Top airlines
Cheapest • from $355 (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 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 • 46% 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

Tue, Jul 21 - Mon, Sep 21
Multiple Airlines Logo
5:35 pm - 5:00 am
OAK
-
ORD
9h 25m
1 stop
Multiple Airlines Logo
6:50 am - 7:44 pm
ORD
-
OAK
14h 54m
1 stop
$352Multiple Airlines
Thu, Jul 9 - Mon, Jul 13
Alaska Airlines Logo
6:49 am - 6:57 pm
OAK
-
ORD
10h 08m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$355Alaska Airlines
Wed, Sep 16 - Mon, Sep 21
Multiple Airlines Logo
3:13 pm - 1:22 pm
OAK
-
ORD
20h 09m
1 stop
Multiple Airlines Logo
6:50 am - 7:44 pm
ORD
-
OAK
14h 54m
1 stop
$358Multiple Airlines
Sat, Sep 5 - Wed, Sep 9
Delta Logo
12:33 pm - 9:30 pm
OAK
-
ORD
6h 57m
1 stop
Delta Logo
2:00 pm - 11:59 pm
ORD
-
OAK
11h 59m
2 stops
$360Delta
Fri, Jul 10 - Sat, Jul 18
Alaska Airlines Logo
7:13 pm - 5:00 am
OAK
-
ORD
7h 47m
1 stop
Alaska Airlines Logo
5:59 pm - 10:41 pm
ORD
-
OAK
6h 42m
1 stop
$364Alaska Airlines
Wed, Sep 2 - Thu, Sep 10
Alaska Airlines Logo
3:13 pm - 7:21 pm
OAK
-
ORD
26h 08m
1 stop
Alaska Airlines Logo
7:20 am - 2:33 pm
ORD
-
OAK
9h 13m
1 stop
$365Alaska Airlines
Sat, Oct 24 - Thu, Oct 29
Delta Logo
5:05 pm - 10:07 am
OAK
-
ORD
15h 02m
2 stops
Delta Logo
7:05 am - 4:32 pm
ORD
-
OAK
11h 27m
2 stops
$366Delta
Fri, Aug 21 - Sun, Aug 23
Multiple Airlines Logo
1:29 pm - 11:59 pm
OAK
-
ORD
8h 30m
1 stop
Multiple Airlines Logo
8:11 pm - 7:42 pm
ORD
-
OAK
25h 31m
1 stop
$367Multiple Airlines
Tue, Oct 6 - Tue, Oct 13
Multiple Airlines Logo
7:00 am - 11:59 pm
OAK
-
ORD
14h 59m
2 stops
Multiple Airlines Logo
6:50 am - 11:18 am
ORD
-
OAK
6h 28m
1 stop
$368Multiple Airlines
Tue, Sep 22 - Fri, Sep 25
Delta Logo
12:29 pm - 9:47 pm
OAK
-
ORD
7h 18m
1 stop
Delta Logo
5:10 pm - 11:59 pm
ORD
-
OAK
8h 49m
2 stops
$369Delta
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 July.

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 $226 (return) on average. On the other hand, the most expensive months are October and March, where the average cost of round-trip tickets is $562 and $534 respectively.

Good to know

Low seasonMarch
Cheapest flight$156
Best time to beat the crowds but there is an average 27% increase in price.
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 5 days, the lowest price for a flight from Oakland to Chicago O'Hare Intl Airport was $156 for a one-way ticket and $352 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 $384 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 3 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 12538 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.0Food
7.0Entertainment
Airline reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

2.0 MediocreJane, Jun 2026
SMF - SEA
Read more Alaska Airlines reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

Never had so many staff members be rude and disrespectful. I had a staff member sarcastically call me “girly” after making me wait 20 minutes to be seen by her. I was able to print my luggage tag and she told me I was too late to check luggage I said the system obviously disagrees. And you had me wait way too long while you asked every single passenger ahead of me about their Disney vacations. She wasted so much time to then say “girly your bag won’t make it on the plane” I’m not her girly I’m a full grown adult. She needs to learn a hell of a lot of respect

My flight was several times rescheduled and then finally canceled.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Flying into PAE was so easy because it’s baggage claim is quick and accesible. I had a car rental and the counter is inside the baggage claim area, very convenient.

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

The first flight was fine, great crew, but the plane was delayed 45 minutes to go to Seattle because of they were missing a ramp. That would make sense if the plane was actually at the gate. Not if we’re still waiting for a plane. After we landed we waited 30-45 minutes on the tarmac just to get off the plane. Alaska made me miss my connecting flight, wasting my time, and my money. I should honestly be reimbursed, but hey, when does the airline ever actually take accountability? Never.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Short trip, was nice to have a drink on the short flight still.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

Was fine, delayed and feels like southwest is always late

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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!

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

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.

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

Information on your arrival and departure airports