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CHI - OAK

$69 Find cheap flights from Chicago to Oakland, California

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 6/11. 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
0 bags
Sat 6/29
Sat 7/6

Search 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland.
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
10:58 pm - 7:41 amORD-OAK
10h 43m1 stop
5:15 am - 9:17 pmOAK-ORD
14h 02m1 stop
$153Spirit Airlines
Find Deal
Tue, Jun 11 - Fri, Jun 14
10:58 pm - 7:41 amORD-OAK
10h 43m1 stop
9:29 pm - 6:36 amOAK-ORD
7h 07m1 stop
$161Spirit Airlines
Find Deal
Tue, Jun 11 - Tue, Jun 18
1:28 pm - 9:00 pmORD-OAK
9h 32m1 stop
11:59 pm - 6:19 pmOAK-ORD
16h 20m1 stop
Wed, Jul 17 - Sun, Jul 21
8:20 pm - 10:49 pmORD-OAK
28h 29m3 stops
5:15 am - 9:17 pmOAK-ORD
14h 02m1 stop
Tue, Jun 11 - Thu, Jun 13
1:24 pm - 11:51 pmMDW-OAK
12h 27m2 stops
10:52 pm - 2:09 pmOAK-MDW
13h 17m2 stops
$407Delta
Find Deal
Wed, Jul 24 - Mon, Jul 29
2:49 pm - 11:51 pmMDW-OAK
11h 02m2 stops
10:52 pm - 9:36 amOAK-MDW
8h 44m1 stop
$461Delta
Find Deal
Wed, Jul 24 - Mon, Jul 29
6:00 am - 9:30 pmMDW-OAK
17h 30m2 stops
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$636Frontier
Find Deal
Thu, Aug 29 - Mon, Sep 2
8:45 pm - 3:59 pmMDW-OAK
21h 14m1 stop
11:59 pm - 8:47 amOAK-MDW
30h 48m1 stop
$667Frontier
Find Deal
Sat, Nov 23 - Sat, Nov 30
10:41 pm - 12:14 pmMDW-OAK
15h 33m1 stop
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$910Volaris
Find Deal
Thu, Jun 27 - Mon, Jul 1
8:50 pm - 8:26 pmMDW-OAK
25h 36m2 stops
11:30 pm - 12:51 pmOAK-MDW
11h 21m1 stop
$964Volaris
Find Deal
Wed, Jun 26 - Sun, Jun 30

Flights from Chicago to Oakland - Travel Insights & Trends

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, California flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Oakland, California.
Our data shows that the cheapest route for a one-way flight from Chicago to Oakland, California cost $138 and was between Chicago Midway Airport and Oakland, California. On average, the best prices are found if you fly this route.

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

The average price of all flights from Chicago to Oakland, California clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Oakland on a Wednesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Tuesdays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Oakland, California, 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, California is February, where tickets cost $154 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $439 and $362 respectively.

How many flights are there between Chicago and Oakland, California per day?

Each day, there are between 2 and 3 nonstop flights that take off from Chicago and land in Oakland, California, with an average flight time of 4h 27m. The most common departure time is 5:00 am and most flights take off in the evening. Each week, there are 20 flights. The most frequent day of departure is Saturday, when 15% of all weekly flights depart. The fewest flights depart on a Sunday.

Which cabin class options are there for flights between Chicago and Oakland, California?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Chicago to Oakland?

Early birds can take the earliest flight from Chicago at 5:35 am and will be landing in Oakland, California at 8:00 am.

What’s the latest departure time from Chicago to Oakland?

If you prefer to fly at night, the latest flight from Chicago to Oakland, California jets off at 10:40 pm and lands at 1:10 am.

Good to know

Low season

February

High season

May

Cheapest flight

$69
Best time to beat the crowds with an average 47% drop in price.
Most popular time to fly with an average 12% increase in price.
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, California?

    In the last 3 days, the lowest price for a flight from Chicago to Oakland, California was $69 for a one-way ticket and $153 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 aircraft models fly most regularly from Chicago to Oakland?

    We unfortunately don’t have that data for this specific 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, Delta or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Delta and Alaska Airlines. With an average price for the route of $420 and an overall rating of 8.0, Delta is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $243 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.

See more FAQs

Top tips for finding a cheap flight from Chicago to Oakland

  • 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.
See more tips

Prefer to fly non-stop from Chicago to Oakland?

Find which airlines fly direct from Chicago to Oakland, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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 9192 reviews
8.6Crew
8.2Boarding
7.3Entertainment
7.9Comfort
7.3Food
Airline reviews

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

10.0 ExcellentMark, May 2024ORD - ANC
Read more about Alaska Airlines reviews

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

The one stewardess was rude about helping me put my bag in overhead….she said “ Is it heavy ?” (I am 73 yrs old)

The flight was about an hour late, and there was notable turbulence for a good part of it. But of course, that was not Alaska Air’s fault, and I think the crew did a good job of keeping it safe. Service suffered a little as a result (I wish I had been offered the option of purchasing food). Overall, it was ok, because we landed safe and sound. Thanks!

Flight was delayed 2 hours. Other than that, it was a good flight.

The flight was late getting in, so many were stressed. The snacks for a LONG flight was not enough.

The whole experience went very well except the rest rooms were a disaster

Sat on tarmac for 30 minutes despite staring at three empty gates, one of which we eventually pulled into

Everything was great. Flight was on time with no issues. It was a short connecting flight so ww didn't have food offered. The gate we got off at was very close to our connecting flight gate so that was very easy.

Pilot warned us it was going to be bumpy, which I usually like when it is, but it wasn't, so I spent most of the flight unnecessarily wondering when it was going to get rough. Just can't win sometimes. Ha!

Flight was changed twice. Original flight was scheduled at 5:30pm. Weeks before flight, flight was changed to 7:00pm. On the date of flight, flight was delayed and departed at 9:00pm. This caused many problems and significantly affected our schedule at our destination.

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

Bag drop off was slow and annoying. Only 2 agents at the entire delta desk, and no one directing traffic for what line to be in, many confused people slowed down the process. Boarding was fine. Seats in Delta comfort plus were fine. Snacks were great! Definitely a bonus. The entertainment system was awful — old, slow, not responsive, and completely unable to play games due to some kind of error. But on the other hand, thank you to Delta for the free WiFi. That made it better.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

They stuck us with multiple extra fees. I will never fly spirit again

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

Minimalist interiors are great for legroom but terrible for comfort.

Seats are extremely cramped. There was't any type of complementary snacks and there was zero entertainment provided beyond purchaseable wifi.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

See my previous comment which is mostly about our flight from Phoenix to SFO

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Book cheap flights from Chicago to Oakland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Oakland found on KAYAK in the last 72 hours.
6/11Tue
1 stopSpirit Airlines
10h 43mORD-OAK
$69
8/28Wed
1 stopSpirit Airlines
10h 27mORD-OAK
$82
7/18Thu
1 stopSun Country Air
12h 07mORD-OAK
$96
7/4Thu
1 stopDelta
9h 14mORD-OAK
$118
7/8Mon
1 stopSun Country Air
11h 24mORD-OAK
$135
6/21Fri
1 stopDelta
6h 35mORD-OAK
$169
7/4Thu
2 stopsAlaska Airlines
11h 30mORD-OAK
$207
6/25Tue
1 stopAlaska Airlines
28h 33mORD-OAK
$217
6/24Mon
2 stopsFrontier
17h 30mMDW-OAK
$564
6/20Thu
2 stopsFrontier
15h 50mMDW-OAK
$565

Search by stops

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Last minute flights from Chicago to Oakland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Oakland that are departing in the next 10 days.
6/4Tue
multi-stopSpirit Airlines
27h 06mORD-OAK
6/11Tue
multi-stopSpirit Airlines
28h 52mOAK-ORD
$192
6/4Tue
multi-stopSpirit Airlines
15h 33mORD-OAK
6/11Tue
multi-stopSpirit Airlines
16h 58mOAK-ORD
$200
6/4Tue
multi-stop
29h 38mORD-OAK
6/11Tue
multi-stop
30h 31mOAK-ORD
$269
6/3Mon
multi-stop
18h 57mORD-OAK
6/6Thu
multi-stop
14h 02mOAK-ORD
$340
5/31Fri
multi-stopAlaska Airlines
29h 00mORD-OAK
6/3Mon
multi-stopAlaska Airlines
7h 18mOAK-ORD
$684
5/31Fri
multi-stopAlaska Airlines
11h 05mORD-OAK
6/3Mon
multi-stopAlaska Airlines
7h 18mOAK-ORD
$805
6/1Sat
multi-stopFrontier
16h 10mMDW-OAK
6/4Tue
multi-stopFrontier
13h 13mOAK-MDW
$893
5/31Fri
multi-stopFrontier
17h 30mMDW-OAK
6/12Wed
multi-stopFrontier
21h 48mOAK-MDW
$921
6/3Mon
multi-stopDelta
11h 36mMDW-OAK
6/5Wed
multi-stopDelta
9h 16mOAK-MDW
$1,034
6/2Sun
multi-stopDelta
8h 04mMDW-OAK
6/4Tue
multi-stopDelta
13h 05mOAK-MDW
$1,044

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Flights to Oakland

Destination:

Oakland (OAK)United States

Return flight deals:

Oakland - Chicago

Cabin classes:

Compare transportation modes for Chicago to Oakland

Average priceAverage duration
Flights9h 32m
Trains$5120h 00m