CHI - OAK

$53 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 8/30. 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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Flights 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, Sep 9 - Sat, Oct 18
Southwest Logo
6:40 am - 11:10 amMDW-OAK
6h 30m1 stop
Southwest Logo
9:05 am - 3:15 pmOAK-MDW
4h 10mnonstop
$119Southwest
Find Deal
Tue, Sep 9 - Sat, Oct 18
Southwest Logo
6:15 am - 1:40 pmORD-OAK
9h 25m1 stop
Southwest Logo
3:05 pm - 11:40 pmOAK-ORD
6h 35m1 stop
$125Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
12:55 pm - 7:35 pmMDW-OAK
8h 40m1 stop
Southwest Logo
5:35 am - 1:45 pmOAK-MDW
6h 10m1 stop
$125Southwest
Find Deal
Wed, Aug 6 - Sat, Aug 9
Spirit Airlines Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
Spirit Airlines Logo
6:00 am - 2:13 pmOAK-ORD
6h 13m1 stop
$128Spirit Airlines
Find Deal
Tue, Sep 9 - Sat, Oct 18
Southwest Logo
6:15 am - 12:40 pmORD-OAK
8h 25m2 stops
Southwest Logo
3:05 pm - 11:40 pmOAK-ORD
6h 35m1 stop
$130Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
3:20 pm - 8:45 pmMDW-OAK
7h 25m2 stops
Southwest Logo
9:45 am - 7:05 pmOAK-MDW
7h 20m1 stop
$130Southwest
Find Deal
Tue, Jul 29 - Tue, Aug 12
Spirit Airlines Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
Spirit Airlines Logo
6:00 am - 2:13 pmOAK-ORD
6h 13m1 stop
$138Spirit Airlines
Find Deal
Thu, Aug 7 - Tue, Aug 12
Alaska Airlines Logo
6:00 am - 12:01 amORD-OAK
20h 01m1 stop
Alaska Airlines Logo
7:00 am - 11:59 pmOAK-ORD
14h 59m1 stop
$182Alaska Airlines
Find Deal
Sat, Aug 9 - Sat, Aug 16
 Logo
3:18 pm - 11:33 pmORD-OAK
10h 15m1 stop
 Logo
8:00 am - 1:07 pmOAK-ORD
27h 07m1 stop
Sat, Aug 23 - Sat, Aug 30
 Logo
2:07 pm - 7:18 pmORD-OAK
7h 11m1 stop
 Logo
6:00 am - 4:50 amOAK-ORD
20h 50m1 stop
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
Useful Info

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.

How much is a round-trip flight from Chicago to Oakland, California?

What is the cheapest Chicago to Oakland flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Oakland.

Our data shows that the cheapest route for a return flight from Chicago to Oakland cost $313 and was between Chicago Midway Airport (MDW) and Oakland (OAK). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $313.

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 July, where tickets cost $247 (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 $382 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.

Good to know

Low seasonApril
High seasonSeptember
Cheapest flight$53
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago Midway 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 $53 for a one-way ticket and $119 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 Midway 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 $373 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 $367 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 $313 or less one-way and $580 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 5 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
7.1Food
7.8Comfort
8.1Boarding
7.1Entertainment
8.5Crew
Airline reviews

10 hour delay. Fuel spill. Crew had to drive to Indianapolis to a get a plane. The longest day of travel ever. Poor service.Little to no communication.

2.0 MediocreMichael, Jul 2025ORD - SEA
Read more Alaska Airlines reviews

10 hour delay. Fuel spill. Crew had to drive to Indianapolis to a get a plane. The longest day of travel ever. Poor service.Little to no communication.

I had a negative experience, the flight delay was very long, I didn't like it

Original flight was canceled, and the automatically booked second flight was immediately delayed. I arrived about 4 hours later than planned with only a $12 meal voucher that didn't fully cover a sandwich at airport prices.

It was very good and comfortable, Crew was also great

Good experience, although it was a little cramped being a tall person. Otherwise everything went smoothly and professionally though

Delay of more than 3 hours I didnt recieve neither a voucher for food Attention disaster

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

The seats in first class are very dated and quite uncomfortable. I don’t need lie-flat seats for a 6 hour flight, but more recline is really necessary.

One of the stewardess, Tre, went above and beyond to ensure my comfort!

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

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.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

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

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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

hahaha we are delayed for one hour plus.. but thx we arrived San Diego safe

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.

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