OAK - ORD

$101 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 5/9. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$201
Typical prices: $421-$306
Delta
Mon 6/1Thu 6/4
OAK - ORD • 1 stop
Cheapest one-way
$101
Typical prices: $156-$264
Delta
Sat 5/9
OAK - ORD • 1 stop
Top airlines
Cheapest • from $201 (round-trip)
Best reviews • 8.0 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 $280 (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

Mon, Jun 1 - Thu, Jun 4
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$201Delta
Mon, Jun 1 - Thu, Jun 4
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$211Delta
Thu, May 28 - Thu, Jun 4
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$216Delta
Thu, May 28 - Wed, Jun 3
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
5:41 pm - 11:57 pm
ORD
-
OAK
8h 16m
2 stops
$221Delta
Tue, May 5 - Tue, May 12
Alaska Airlines Logo
10:57 am - 1:13 pm
OAK
-
ORD
24h 16m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$257Alaska Airlines
Sat, Apr 25 - Thu, Apr 30
Delta Logo
12:34 pm - 9:18 pm
OAK
-
ORD
6h 44m
1 stop
Delta Logo
7:10 pm - 11:54 pm
ORD
-
OAK
6h 44m
1 stop
$261Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
5:57 pm - 11:54 pm
ORD
-
OAK
7h 57m
2 stops
$262Delta
Sun, May 24 - Thu, Jun 4
Delta Logo
6:00 am - 4:29 pm
OAK
-
ORD
8h 29m
2 stops
Delta Logo
7:45 pm - 11:57 pm
ORD
-
OAK
6h 12m
1 stop
$266Delta
Tue, May 5 - Tue, May 12
Southwest Logo
6:10 am - 6:50 pm
OAK
-
ORD
10h 40m
2 stops
Southwest Logo
7:45 am - 3:30 pm
ORD
-
OAK
9h 45m
2 stops
$267Southwest
Sat, May 2 - Tue, May 5
Southwest Logo
12:55 pm - 10:20 pm
OAK
-
ORD
7h 25m
1 stop
Southwest Logo
7:45 am - 1:30 pm
ORD
-
OAK
7h 45m
1 stop
$271Southwest
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 June.

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$101
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 $101 for a one-way ticket and $201 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 $373 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 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.
8.0
SouthwestOverall score based on 4338 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

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.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Crew were bad Didn’t help with luggage When asked for a glass of wine, I was told that they will serve later , which they didn’t to Me and didn’t serve anyone else in First class . Didn’t offer any snacks , Chips or Nuts to anyone . Flight was not crowded either. Worst Service/ or No Service !

A solidly good experience, but would’ve appreciated more communication with regards to travel delays.

Alaska is consistently the best in all categories. Excellent airlines and employees

My daughter has anxiety and became nauseous after boarding the plane and before take off. She went to the plane bathroom and ended up having to vomit, and your staff promptly removed us from the flight. We explained that it was due to my daughter’s anxiety, and that the condition would not continue in the air, but they removed us anyway. We have flown many many times before on many different airlines and my daughter’s anxiety has resulted in nausea and sickness before takeoff, and every airline has been accommodating and professional. This is was our first time flying with your airline, and also the first time we have ever been removed from a flight. This was the worst service we have ever experienced. This was a special surprise trip we gifted to my daughter for graduating college. I had also paid to upgrade the family to first class and sit all together which we had never done before and can’t afford on a normal basis. Our removal from the flight was not only extremely embarrassing, but devastating for my daughter. My daughter and I were removed from the plane and a call was made by your staff to medical personnel, a few questions were asked of my daughter, and then she was magically cleared. All of this took mere minutes. Why this could not have been performed while we were on the plane, or why this could not have been performed off the plane and then us allowed to reboard is beyond me. My wife and youngest daughter continued on the original flight alone and were very upset and crying due to the situation, yet the staff did nothing to console or assist them. My wife states that upon arrival in Portland and as they were exiting the plane, one of the stewardesses involved said “byyyyeeeee” to them sarcastically and laughed. Myself and my oldest daughter had to wait 4 hours for an alternate flight and were sat in regular seats because our first class seat purchase could not be honored. My wife wasn’t allowed to pick up our rental car and had to wait 4 hours with our luggage until I arrived. The delay prevented us from being able to carry out planned events and ruined the first day of our trip. Upon explaining all of this to your customer service, we received no sympathy, assistance, or compensation other than your staff submitting a request for a reimbursement of my and my daughters first class upgrade cost. When checking in early for our flight back home, the luggage cost for myself and my eldest daughter was no longer discounted as it was for my wife and youngest daughter. Customer service once again could not assist me over the phone and rectify what should have been a minor adjustment. Instead they stated I would have to wait until we physically checked bags in at the airport and then ask staff to adjust the luggage cost. With everything else we had experienced, I was not going to leave that to chance and instead paid full price for the luggage ahead of time. Or experience with Alaska Airlines was a complete disaster and I am baffled at the lack of empathy and assistance from your staff. I’m not sure of what else to say other than the fact that unless we are compensated by Alaska Airlines in some form to offset the horrendous service we received, we will be relaying our experience to family and friends and on social media, and doing all we can to urge everyone to avoid utilizing your services.

All airlines should board planes back to front, instead of catering to higher priced tickets. The boarding groups are inefficient and delay takeoff time

I got an email 3 hours before the flight letting me know it got canceled

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

No issues and clear sailing. What a preferred to have sat in one of empty seats other than my assigned seat that would be my only complaint if it was to complain.

A TV Screen and movies would have been a great addition. The Alaska Terminal at JFK is TOO BIG!!! You need to go up and down 3 escalators to get to your gate and to baggage claim -- and all this while you are carrying your backpack, other bags, etc. I don't know what they were thinking. You can easily miss a flight if you don't add in at least 30 minuites to get to a gate.

Luggage was severely damaged. Flight was late for several hours

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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

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.

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.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

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

Information on your arrival and departure airports