OAK - ORD

$119 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 3/1. 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 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
$258
Typical prices: $171-$363
Alaska Airlines
Fri 2/6Tue 2/10
OAK - ORD • 1 stop
Cheapest one-way
$119
Typical prices: $170-$196
Hawaiian Airlines
Sun 3/1
OAK - ORD • 1 stop
Top airlines
Alaska Airlines
Cheapest • from $258 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 42% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Fri, Feb 6 - Tue, Feb 10
Alaska Airlines Logo
5:17 pm - 2:38 pmOAK-ORD
19h 21m1 stop
Alaska Airlines Logo
8:00 am - 4:23 pmORD-OAK
10h 23m1 stop
$258Alaska Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
Delta Logo
12:30 pm - 9:21 pmOAK-ORD
6h 51m1 stop
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
$259Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:35 pm - 5:04 amOAK-ORD
8h 29m1 stop
Alaska Airlines Logo
7:45 am - 5:43 pmORD-OAK
11h 58m1 stop
$260Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:30 am - 5:04 amOAK-ORD
20h 34m1 stop
Alaska Airlines Logo
6:50 pm - 11:38 pmORD-OAK
30h 48m1 stop
$262Alaska Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
Delta Logo
5:55 am - 4:57 pmOAK-ORD
9h 02m2 stops
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
$264Delta
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Tue, Dec 16 - Thu, Dec 25
Alaska Airlines Logo
2:31 pm - 11:59 pmOAK-ORD
7h 28m1 stop
Alaska Airlines Logo
8:00 am - 2:07 pmORD-OAK
8h 07m1 stop
$268Alaska Airlines
Find Deal
Fri, Feb 6 - Mon, Feb 9
Southwest Logo
5:10 am - 1:30 pmOAK-ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 10:45 pmORD-OAK
10h 30m2 stops
$294Southwest
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Fri, Feb 6 - Mon, Feb 9
Southwest Logo
8:55 pm - 1:30 pmOAK-ORD
14h 35m2 stops
Southwest Logo
2:15 pm - 10:45 pmORD-OAK
10h 30m2 stops
$305Southwest
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Sun, Feb 15 - Thu, Feb 19
Southwest Logo
5:10 am - 1:30 pmOAK-ORD
6h 20m1 stop
Southwest Logo
7:15 am - 4:45 pmORD-OAK
11h 30m2 stops
$324Southwest
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Thu, Jan 8 - Tue, Jan 13
Southwest Logo
5:25 am - 1:30 pmOAK-ORD
6h 05m1 stop
Southwest Logo
4:25 pm - 9:45 pmORD-OAK
7h 20m1 stop
$329Southwest
Find Deal
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 February.

What’s the cheapest day of the week to fly from Oakland to Chicago O'Hare Airport?

The average price of all round-trip flights from Oakland to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

For Oakland to Chicago O'Hare Airport, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago O'Hare Airport back to Oakland, the best deals are generally found on Wednesday, with Friday being the most expensive.

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 February, where tickets cost $216 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $508 and $462 respectively.

Good to know

Low seasonJanuary
Cheapest flight$119
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 2% 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 $119 for a one-way ticket and $258 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Oakland and Chicago O'Hare Airport, with oneworld 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 $389 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $356 and an overall rating of 8.0.

  • 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.
8.0
Alaska AirlinesOverall score based on 11241 reviews
7.1Food
8.5Crew
7.8Comfort
7.0Entertainment
8.1Boarding
Airline reviews

If they actually let me fly. I was rerouted to United and there was no Alaska airlines reps at all. Then the lady who worked the delta counter told me to go away and figure things out myself. Horrible experience.

2.0 MediocreAnonymous, Nov 2025SBA - PDX
Read more Alaska Airlines reviews

If they actually let me fly. I was rerouted to United and there was no Alaska airlines reps at all. Then the lady who worked the delta counter told me to go away and figure things out myself. Horrible experience.

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Sitting on the ground for 2 hours waiting for a gate wasn't fun.

It was a great experience, friendly staff and good snacks

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

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

Information on your arrival and departure airports