CHI - OAK

$119 Find Cheap Flights from Chicago to Oakland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Oakland departing on 1/20. 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 Oakland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, 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 Chicago to Oakland, 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
$251
Overall average: $301
Alaska Airlines
Tue 2/10Wed 2/18
ORD - OAK • 1 stop
Cheapest non-stop
$265
Southwest
Thu 1/29Tue 2/3
MDW - OAK • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Chicago Midway offers shorter security lines than ORD.
From OAK, Uber or Lyft are convenient transport options.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Alaska Airlines
Cheapest • from $251 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-OAK
Cheapest
MDW-OAK
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 37% price drop
March
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 Oakland!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Oakland (CHI-OAK)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Oakland 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 Chicago to Oakland

Tue, Feb 10 - Wed, Feb 18
Alaska Airlines Logo
8:00 am - 4:23 pm
ORD
-
OAK
10h 23m1 stop
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m1 stop
$251Alaska Airlines
Sat, Jan 17 - Tue, Feb 3
Delta Logo
5:20 pm - 9:38 pm
ORD
-
OAK
6h 18m1 stop
Delta Logo
12:33 pm - 9:52 pm
OAK
-
ORD
7h 19m1 stop
$252Delta
Wed, Feb 18 - Sat, Feb 21
Alaska Airlines Logo
3:54 pm - 10:49 pm
ORD
-
OAK
8h 55m1 stop
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m1 stop
$255Alaska Airlines
Sat, Jan 17 - Sat, Jan 24
Delta Logo
5:20 pm - 9:38 pm
ORD
-
OAK
6h 18m1 stop
Delta Logo
12:33 pm - 9:52 pm
OAK
-
ORD
7h 19m1 stop
$256Delta
Sat, Jan 17 - Wed, Feb 4
Delta Logo
5:20 pm - 9:38 pm
ORD
-
OAK
6h 18m1 stop
Delta Logo
5:55 am - 5:55 pm
OAK
-
ORD
10h 00m2 stops
$257Delta
Tue, Jan 20 - Fri, Jan 30
Alaska Airlines Logo
2:06 pm - 9:46 am
ORD
-
OAK
21h 40m1 stop
Alaska Airlines Logo
8:10 am - 11:50 pm
OAK
-
ORD
13h 40m1 stop
$259Alaska Airlines
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
11:10 am - 2:05 pm
MDW
-
OAK
4h 55mnonstop
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
$265Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
11:10 am - 2:05 pm
MDW
-
OAK
4h 55mnonstop
Southwest Logo
5:40 am - 11:40 am
OAK
-
MDW
4h 00mnonstop
$273Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
11:10 am - 2:05 pm
MDW
-
OAK
4h 55mnonstop
Southwest Logo
12:10 pm - 9:15 pm
OAK
-
MDW
7h 05m1 stop
$275Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
8:10 am - 2:55 pm
MDW
-
OAK
8h 45m2 stops
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
$280Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Oakland flights

Get data-powered insights and trends into flights from Chicago to Oakland to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Oakland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Oakland costs $326 on the route between Chicago Midway Airport (MDW) and Oakland (OAK). It is also the most popular route.

What is the cheapest month to fly from Chicago to Oakland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Oakland, 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 Chicago to Oakland is September, where tickets cost $252 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $711 and $562 respectively.

Can I save money by flying with a layover from Chicago to Oakland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $391, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Chicago to Oakland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

MDW offers a user-friendly experience with shorter security lines than ORD, making it ideal for domestic flights.

OAK

For transport from OAK, Uber or Lyft are recommended, but BART is a cheaper option during rush hour.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on OAK

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Good to know

Low seasonNovember
Cheapest flight$119
Best time to beat the crowds but there is an average 78% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago O'Hare Airport to Oakland

When to book flights from Chicago to Oakland

Are your dates flexible? Find out the best times to travel from Chicago to Oakland 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 flights from Chicago to Oakland

  • Are there lounges in O'Hare International Airport (ORD) where passengers can await their departures?

    There are various lounge facilities within the different terminals at the airport. The main lounge in Terminal 1 is the United Club by United airlines which has four lounges: near Gates C16, C18, B18, and B6. The other is the Delta Sky Club in Terminal 2, where United Club also has a place on the grid. There are also multiple other lounge facilities in Terminal 3, mainly occupied by American Airlines. Additionally, the Admiral Club lounges are located between Gates H6 and K6, Gate L1, and near Gate G8. Terminal 5 has some lounges in it.

  • Are there any hotels near Oakland International Airport (OAK)?

    The SpringHill Suites by Marriott Oakland Airport is among the most convenient hotels where you can book a room in the case of late arrival at the airport. It is located 1.7 miles away and has facilities such as an indoor spa.

  • Are there Pet Relief Areas in O'Hare International Airport (ORD)?

    There are several Pet Relief Areas in O'Hare International Airport (ORD). An area inside Terminal 1's lower level is accessible by taking the elevator to the lower level and proceeding to the Baggage Claim, exit through Door 1A, and you will have the area on your left. Terminal 2's location is accessible by taking the elevator to the lower level, exiting through Door 2E, and the site will also be on your left. Terminal 3 is located inside the Main Hall of the airport next to the Lotto booth found near Gate K1.

  • What flights are available from O’Hare International Airport (ORD) to Oakland International Airport (OAK)?

    There are both direct and connecting flights between the destinations. Spirit Airlines is the only airline that offers direct flights between the destinations. However, they also have flights with a layover at Harry Reid International Airport (LAS). Delta Airlines also makes flights with a layover at Salt Lake City International Airport (SLC).

  • What is the cheapest flight from Chicago to Oakland?

    In the last 3 days, the lowest price for a flight from Chicago to Oakland was $119 for a one-way ticket and $251 for a round-trip.

  • Do I need a passport to fly between Chicago and Oakland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago to Oakland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Oakland (Oakland). The cheapest flights are generally found on the Chicago O'Hare Airport to Oakland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Oakland?

    American Airlines, Hawaiian Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to Oakland flight route.

  • Which aircraft models fly most regularly from Chicago to Oakland?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to Oakland flight route.

  • On which days can I fly direct from Chicago to Oakland?

    There are nonstop flights from Chicago to Oakland on a daily basis.

  • Which is the best airline for flights from Chicago to Oakland, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and Delta. With an average price for the route of $387 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $359 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to Oakland?

    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 Chicago to Oakland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Oakland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Oakland from Chicago 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 Chicago to Oakland?

    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 Oakland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Oakland?

    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 Oakland from Chicago 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 Chicago to Oakland

  • Looking for a cheap flight? 25% of our users found flights on this route for $181 or less one-way and $627 or less round-trip.
  • Two international airports serve the city of Chicago. Although the O'Hare International Airport (ORD) is the central hub for flights around the city, the Midway International Airport (MDW) is closer to downtown Chicago of the two airports. They are located 18 miles and 12.5 miles away from the city center.
  • The BART train is the best way to get from the Oakland International Airport (OAK) to downtown Oakland. It costs around $6 for a ticket, and you can catch it at the station located at the Coliseum. It will take you 10min to complete the journey.
  • Travelers to Oakland can rely on three airports for their transportation needs: Norman Y. Mineta International Airport, Oakland International Airport (OAK), and Reid Hillview Airport. The former Oakland International (OAK) is the most convenient option for traveling to the city since it's 6 miles distance from the center of Oakland.
  • The most convenient way to move from downtown to O'Hare International Airport (ORD) is via the Blue Line, which only takes 45min to complete the journey and around $5 as a fare.
  • On the curbside of Terminal 2, you will find wheelchairs in the Oakland International Airport (OAK). If you have mobility challenges, it would be better to use the services offered in Terminal 2. It would also be better to contact your airlines before traveling for arranged assistance.

Prefer to fly direct from Chicago to Oakland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Oakland.
Find which airlines fly direct from Chicago to Oakland Airport, which days they fly and book direct flights.

Direct departures

Chicago to Oakland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Oakland to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 4 airlines serving from Chicago to Oakland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oakland. 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 Chicago to Oakland? 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 4250 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

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.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

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.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

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

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Connecting flight is on time and boarding was a breeze!

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

Food was surprisingly good but the WiFi was not great

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

The plane was freezing and everyone had on their winter coats. I pulled out my sweaters out of my carryon to cover myself and put on an extra pair of socks. They offered NO FREE drinks or snacks on a 6 hour flight. The seats don’t have plugs or charges or any form of entertainment- so I just played my one downloaded game on my phone because I couldn’t sleep because I was too cold. Miserable flight though we landed safely.

Always comes in handy when I want a quick weekend getaway.

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

No Tumberlence smooth flight. Try to change the menu on Snacks.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Everything you need to know for your flight from Chicago to Oakland

Information on your arrival and departure airports