OAK - ORD

$99 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 5/13. 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
$197
Overall average: $381
Alaska Airlines
Tue 5/19Wed 5/20
OAK - ORD • 1 stop
Cheapest one-way
$99
Typical prices: $138-$213
Alaska Airlines
Wed 5/13
OAK - ORD • 1 stop
Top airlines
Alaska Airlines
Cheapest • from $197 (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 • 39% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, May 19 - Wed, May 20
Alaska Airlines Logo
7:00 am - 6:46 pm
OAK
-
ORD
9h 46m
1 stop
Alaska Airlines Logo
9:00 am - 2:32 pm
ORD
-
OAK
7h 32m
1 stop
$197Alaska Airlines
Sat, Feb 28 - Sat, Mar 7
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m
1 stop
Alaska Airlines Logo
5:29 pm - 11:54 pm
ORD
-
OAK
8h 25m
1 stop
$217Alaska Airlines
Tue, Apr 14 - Sat, Apr 18
Southwest Logo
3:00 pm - 11:55 pm
OAK
-
ORD
6h 55m
1 stop
Southwest Logo
4:15 pm - 9:00 pm
ORD
-
OAK
6h 45m
1 stop
$218Southwest
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
6:41 am - 7:03 pm
OAK
-
ORD
10h 22m
1 stop
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$223Alaska Airlines
Tue, Apr 21 - Tue, Apr 28
Alaska Airlines Logo
6:40 pm - 6:40 am
OAK
-
ORD
10h 00m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$230Alaska Airlines
Wed, May 13 - Sat, May 16
Alaska Airlines Logo
10:29 am - 6:46 pm
OAK
-
ORD
6h 17m
1 stop
Alaska Airlines Logo
9:00 am - 11:37 pm
ORD
-
OAK
16h 37m
1 stop
$233Alaska Airlines
Sat, Feb 28 - Mon, Mar 2
Delta Logo
12:40 pm - 9:52 pm
OAK
-
ORD
7h 12m
1 stop
Delta Logo
6:45 pm - 11:51 pm
ORD
-
OAK
7h 06m
1 stop
$237Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
5:55 am - 6:01 pm
OAK
-
ORD
10h 06m
2 stops
Delta Logo
7:10 pm - 11:46 pm
ORD
-
OAK
6h 36m
1 stop
$242Delta
Mon, Apr 27 - Fri, May 1
Alaska Airlines Logo
3:18 pm - 11:43 pm
OAK
-
ORD
6h 25m
1 stop
Alaska Airlines Logo
3:52 pm - 6:15 pm
ORD
-
OAK
28h 23m
1 stop
$243Alaska Airlines
Thu, Mar 5 - Tue, Mar 10
Delta Logo
5:55 am - 6:01 pm
OAK
-
ORD
10h 06m
2 stops
Delta Logo
1:57 pm - 11:46 pm
ORD
-
OAK
11h 49m
2 stops
$247Delta
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.

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 $238 (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 seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 40% drop 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 $99 for a one-way ticket and $197 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 $385 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 $532 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 11839 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.1Food
7.0Entertainment
Airline reviews

The room for legs is adequate for a 6’ tall man and the flight was comfortable. The cabin is clean and the crew is very friendly and pleasant.

10.0 ExcellentPhilip, Feb 2026
SAN - TPA
Read more Alaska Airlines reviews

The room for legs is adequate for a 6’ tall man and the flight was comfortable. The cabin is clean and the crew is very friendly and pleasant.

The he whole flight was very smooth on every aspects.

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

My TSA pre check was left Off my boarding pass which was a large inconvenience.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

Overall it was fine, however one of my two checked bags did not arrive and I was told it was left in Palm Springs. I don't understand how one of the two bags made it through fine but the other got lost .

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

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

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

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

Information on your arrival and departure airports