OAK - ORD

$129 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 8/4. 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

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Everything you should know

Cheapest round-trip
$257
Typical prices: $292-$512
Alaska Airlines
Tue 8/11Tue 8/18
OAK - ORD • 1 stop
Cheapest one-way
$129
Typical prices: $98-$193
Alaska Airlines
Tue 8/4
OAK - ORD • 1 stop
Top airlines
Cheapest • from $257 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Oakland and O'Hare Intl. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $233 (round-trip)
Shortest trip • 6h 08m (one-way)
Insights
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Insights
When to travel
Cheapest • 46% price drop
Most popular
Good to know
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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, Aug 11 - Tue, Aug 18
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:20 am - 2:10 pm
ORD
-
OAK
9h 50m
1 stop
$257Alaska Airlines
Tue, Aug 11 - Mon, Aug 17
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$261Alaska Airlines
Sat, Oct 17 - Mon, Oct 26
Delta Logo
12:31 pm - 10:00 pm
OAK
-
ORD
7h 29m
1 stop
Delta Logo
7:30 pm - 11:56 pm
ORD
-
OAK
6h 26m
1 stop
$265Delta
Thu, Aug 13 - Thu, Aug 20
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:01 am - 11:06 am
ORD
-
OAK
7h 05m
1 stop
$269Alaska Airlines
Sat, Oct 17 - Sat, Oct 24
Delta Logo
12:31 pm - 10:00 pm
OAK
-
ORD
7h 29m
1 stop
Delta Logo
5:30 am - 4:23 pm
ORD
-
OAK
12h 53m
2 stops
$270Delta
Mon, Aug 10 - Wed, Aug 19
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:01 am - 11:06 am
ORD
-
OAK
7h 05m
1 stop
$273Alaska Airlines
Wed, Sep 2 - Wed, Sep 9
Multiple Airlines Logo
12:13 pm - 7:02 pm
OAK
-
ORD
28h 49m
1 stop
Multiple Airlines Logo
7:20 am - 2:33 pm
ORD
-
OAK
9h 13m
1 stop
$279Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Frontier Logo
8:39 pm - 5:42 am
OAK
-
ORD
7h 03m
1 stop
Frontier Logo
6:50 am - 11:18 am
ORD
-
OAK
6h 28m
1 stop
$281Frontier
Wed, Sep 2 - Wed, Sep 9
Multiple Airlines Logo
12:13 pm - 7:02 pm
OAK
-
ORD
28h 49m
1 stop
Multiple Airlines Logo
2:18 pm - 9:28 pm
ORD
-
OAK
9h 10m
1 stop
$288Multiple Airlines
Mon, Aug 10 - Thu, Aug 20
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:01 am - 11:06 am
ORD
-
OAK
7h 05m
1 stop
$289Alaska 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 August.

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$129
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 $129 for a one-way ticket and $257 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 $383 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 12607 reviews
7.0Entertainment
7.8Comfort
8.5Crew
7.1Food
8.1Boarding
Airline reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

4.0 OkayDave, Jun 2026
FSD - ORD
Read more Alaska Airlines reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

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.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

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.

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.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

There was no coffee on the flight. I was very surprised. I know it is a small thing, but they seemed to have run out of other drinks.

If Alaska Air is going to partner with other airlines, then it has to make the transition to the connecting flight better, especially if Alaska Air is the one that is running late. When I realized our 30 minutes of lateness due to weather was going to make getting to my connecting flight home more difficult ,I would have expected more from the crew than blank stares and "sorry". My son and I had 20 minutes to get from Gate E to the end of Gate K in the Chicago airport. My 50+ year-old body had to sprint and yell to get through the throngs and have any chance of arriving to the gate on time. In addition, the seats I had chosen when I purchased the connecting flight were changed so that my son and I placed in the last rows next to the bathrooms and were separated. There needs to be better communication between the airlines if one is going to be late. The thought of not making it home on time (we still had an 1.5 hour drive to get there) was stressful and unnecessary.

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.

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.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Wifi didn’t work, no service, seats are hard as rocks

Southwest Airlines is behind the times with a woefully inefficient service animal policy that leads to major inconsistency and stress for passengers and crew alike. Despite so many attempts to share feedback and request better support, they bungled it once again and provoked a panic attack in the process, with no apologies or acknowledgment that their crew was failing to adhere to their own inadequate policies. WiFi didn’t work, flight was delayed by an hour, it was about what I’ve come to expect from Southwest these days.

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

I always know what to expect from Southwest - friendly crew, on time departures. I like getting free baggage. The app works great and the in-flight entertainment passes the time.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

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.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

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

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