CHI - OAK

$63 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 10/1. 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

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
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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, Sep 23 - Wed, Sep 24
Spirit Airlines Logo
11:15 am - 11:32 pmORD-OAK
14h 17m1 stop
Spirit Airlines Logo
6:30 am - 6:51 pmOAK-ORD
10h 21m1 stop
$143Spirit Airlines
Find Deal
Tue, Sep 23 - Wed, Sep 24
Spirit Airlines Logo
11:15 am - 11:32 pmORD-OAK
14h 17m1 stop
Spirit Airlines Logo
10:56 am - 9:32 pmOAK-ORD
8h 36m2 stops
$148Spirit Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
Spirit Airlines Logo
11:15 am - 11:32 pmORD-OAK
14h 17m1 stop
Spirit Airlines Logo
8:44 am - 2:27 pmOAK-ORD
27h 43m1 stop
$151Spirit Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
Spirit Airlines Logo
11:15 am - 11:32 pmORD-OAK
14h 17m1 stop
Spirit Airlines Logo
6:00 am - 2:27 pmOAK-ORD
6h 27m1 stop
$159Spirit Airlines
Find Deal
Tue, Sep 30 - Wed, Oct 1
Spirit Airlines Logo
11:15 am - 11:32 pmORD-OAK
14h 17m1 stop
Spirit Airlines Logo
6:30 am - 9:32 pmOAK-ORD
13h 02m1 stop
$166Spirit Airlines
Find Deal
Mon, Sep 15 - Tue, Sep 23
 Logo
9:54 pm - 11:32 pmORD-OAK
27h 38m1 stop
 Logo
6:30 am - 6:51 pmOAK-ORD
10h 21m1 stop
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
10:50 pm - 1:30 amMDW-OAK
4h 40mnonstop
Southwest Logo
5:40 am - 2:25 pmOAK-MDW
6h 45m1 stop
$235Southwest
Find Deal
Tue, Sep 30 - Tue, Oct 7
Southwest Logo
12:50 pm - 6:25 pmMDW-OAK
7h 35m1 stop
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
$257Southwest
Find Deal
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
10:50 pm - 1:30 amMDW-OAK
4h 40mnonstop
Southwest Logo
6:40 am - 12:45 pmOAK-MDW
4h 05mnonstop
$258Southwest
Find Deal
Mon, Nov 24 - Fri, Nov 28
Southwest Logo
7:45 am - 10:25 amMDW-OAK
4h 40mnonstop
Southwest Logo
5:25 am - 11:30 amOAK-MDW
4h 05mnonstop
$261Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Spirit Airlines
Cheapest • from $143 (round-trip)
Alaska Airlines
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 • 28% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$143
Overall average: $265
Spirit Airlines
Tue 9/23Wed 9/24
ORD - OAK • 1 stop
Cheapest non-stop
$258
Southwest
Sat 11/22Thu 11/27
MDW - OAK • Non-stop
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We hope you love your trip to Oakland!
Expert advice

Expert advice for your flight from Chicago to Oakland

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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.

Read more about MDWby Stefanie Waldek
OAK

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

Read more about OAKby Gabriel Leigh
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
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 $253 on the route between Chicago Midway Airport (MDW) and Oakland (OAK). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Oakland?

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

If your flying dates are flexible, you should consider flying to Oakland on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Oakland. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

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 $253 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $446 and $399 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $444 on average.

Good to know

Low seasonApril
Cheapest flight$63
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 28% 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 $63 for a one-way ticket and $143 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 Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and Alaska Airlines. With an average price for the route of $377 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 $393 and an overall rating of 8.0.

  • 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 $234 or less one-way and $589 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
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
7.8Comfort
7.1Food
7.0Entertainment
8.5Crew
Airline reviews

Seattle airport is a mess. New bag tag system has potential, but you need more signage to guide passengers through the process as to where to go next. Told to go in one direction and then met with a very rude agent when we did. He blamed his attitude on all the folks flying over labor day that were paying his salary. Gate area for D3 is a mess compared to the North terminal. Overall Alaska is number 1 in my book.

10.0 ExcellentAnonymous, Aug 2025SEA - SAN
Read more Alaska Airlines reviews

Seattle airport is a mess. New bag tag system has potential, but you need more signage to guide passengers through the process as to where to go next. Told to go in one direction and then met with a very rude agent when we did. He blamed his attitude on all the folks flying over labor day that were paying his salary. Gate area for D3 is a mess compared to the North terminal. Overall Alaska is number 1 in my book.

This time it is good, no delay and right on time

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was a good experience! Thank you:) No sparkling mineral water… 🥲

On time, WiFi worked, reasonable legroom, helpful staff. Unfortunately there was no water for handwashing in the rear lavatory.

The airline staff was great! The best safety review ive ever had!

No food but only snack was provided during the 6-hour flight from EWR to LAX. I was so hungry during the trip.

Miss bigger screens for movies Staff was friendly Seats comfortable Bathroom line long

Agent boarding us in San Diego lectured me on showing up on time for the flight, and said that if I had been three minutes later, he would have denied myself and my wife boarding. Our trusted traveler numbers were not in the system, even though I entered them when I bought the tickets. Our food orders were not in the system, even though I entered them prior to the flight. My wife requires a wheelchair, and that was delayed on both flights.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

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

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

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.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Very good. Nothing more or less than expected. No complaints.

My experience with the spirit as a first time it was OK, but the seats need a little cushion, the problem I had the most impacted me was when checking in the scales were so off and wrong. It will tell that you would have more weight, which was not true. The scale was say that it had Thirty Eight Pounds, when get in the labels when we send the luggage into the band. It says that it was overweight. I really really dislike that because the scales are not accurate. If I use Spirit and I have that issue again. That will be my last time flying with the spirit, even though I like so much to service the planes, and everything else

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.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

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

Information on your arrival and departure airports

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