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CHI - OAK

$49 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 6/4. 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
Mon 6/3
Mon 6/10

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 43,693,958 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
10:52 pm - 11:12 amORD-OAK
14h 20m1 stop
12:02 pm - 9:55 pmOAK-ORD
7h 53m1 stop
$124Spirit Airlines
Find Deal
Tue, May 14 - Wed, May 29
10:52 pm - 11:12 amORD-OAK
14h 20m1 stop
11:22 am - 6:00 amOAK-ORD
16h 38m1 stop
$129Spirit Airlines
Find Deal
Tue, May 21 - Tue, May 28
10:52 pm - 12:25 pmORD-OAK
15h 33m2 stops
8:10 pm - 5:49 amOAK-ORD
7h 39m1 stop
$136Spirit Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
10:57 pm - 8:52 amORD-OAK
11h 55m1 stop
11:22 am - 6:00 amOAK-ORD
16h 38m1 stop
$138Spirit Airlines
Find Deal
Tue, May 21 - Tue, May 28
10:57 pm - 8:52 amORD-OAK
11h 55m1 stop
5:30 am - 9:55 pmOAK-ORD
14h 25m1 stop
$139Spirit Airlines
Find Deal
Tue, May 28 - Tue, Jun 4
1:13 pm - 9:40 pmORD-OAK
10h 27m1 stop
1:15 pm - 9:17 pmOAK-ORD
6h 02m1 stop
$142Spirit Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
8:00 pm - 11:55 pmORD-OAK
29h 55m3 stops
5:30 am - 4:56 pmOAK-ORD
9h 26m1 stop
Fri, May 17 - Wed, May 22
7:20 pm - 11:15 pmORD-OAK
5h 55m1 stop
12:48 pm - 9:42 pmOAK-ORD
6h 54m1 stop
$296Delta
Find Deal
Sat, Jun 29 - Wed, Jul 17
2:15 pm - 11:51 pmMDW-OAK
11h 36m2 stops
5:00 pm - 8:48 amOAK-MDW
13h 48m2 stops
$323Delta
Find Deal
Fri, May 31 - Fri, Jun 7
1:24 pm - 11:55 pmMDW-OAK
12h 31m2 stops
10:55 pm - 12:44 pmOAK-MDW
11h 49m2 stops
$413Delta
Find Deal
Sun, Jun 16 - Mon, Jul 8

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 January, where tickets cost $187 on average. On the other hand, the most expensive months are June and November, where the average cost of tickets is $445 and $445 respectively.

How far in advance should I book a flight from Chicago to Oakland, California?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Oakland, California, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Oakland, California, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 38 days before departure.

Which airlines provide the cheapest flights from Chicago to Oakland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Spirit Airlines ($49) and Sun Country Air ($98). The cheapest round-trip tickets were found on Spirit Airlines ($124) and Delta ($296).

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

Each day, there are between 1 and 4 nonstop flights that take off from Chicago and land in Oakland, California, with an average flight time of 4h 34m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 16 flights. The most frequent day of departure is Tuesday, when 25% of all weekly flights depart. The fewest flights depart on a Saturday.

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

April

High season

March

Cheapest flight

$49
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 5% 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 $49 for a one-way ticket and $124 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 $402 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 $246 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 9128 reviews
8.6Crew
7.9Comfort
7.3Food
7.3Entertainment
8.2Boarding
Airline reviews

My baggage was in another flight, anit was delayed for one hour.

4.0 OkayAnonymous, May 2024SEA - LAX
Read more about Alaska Airlines reviews

My baggage was in another flight, anit was delayed for one hour.

They canceled the flight 30 minutes prior to departure without any heads up.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Up on arrival, due to twisted ankle, I wasn’t able to walk. Requested for a wheelchair. They immediately asked for it. After 10 minutes wait a young man named Carlos picked me up at the gate, got my baggage and took me to the pick up area. It was a great service. Thanks Alaska Air line

Staff great. Tight seating. Pretzels and drink same as any other airline.

We had a very scary attempted landing in Palm Springs and were redirected to Ontario. It was a stressful flight.

Every thing means , crew, service, timing, boarding is very good.

My boarding pass birthdate was printed incorrectly causing me to spend an extra hour in a check-in and then again TSA line and to miss a chance to have dinner pre-flight. My window seat was given away and was replaced with a middle seat. I would have liked an opportunity to charge my phone and take advantage of movies but many of the departure gate chargers weren’t operational and I don’t know of an in-flight charging option, The flight left 45 late after trouble with unruly passengers, and I was glad staff removed them.

Horrible. I likely will have to spend several thousand dollars to rebook my international flights, due to their delays, plus a hotel in SF. I can’t wait to never fly them again!

Pleasant flight, now wifi, but did get pushed to the exit row gracefully cause I am a tall man. Was a pleasant thank you.

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

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Crew was not friendly when I went to request a seat change.

Really impressive staff at airport and on plane, especially given how busy it was

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.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

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.

They charged me 212.00 for a heavy check in bag at the gate. The pricing and process was so confusing - as if it was designed to purposefully gouge customers who need to board plane. That experience combined with the outrageous price charged will prevent me from ever flying Spirit again. And I’ll be sure to tell the story to anyone who cares to hear.

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.

Seats could use more padding. Kind of hard on the tush.

Amazed that Spirit can even get planes in the air, would never use again.

The flight was really great I was surprised with Spirit.

Spirit canceled the flight 20 hours before it was scheduled to take off. They didn’t send a clear message and had no alternative flight for a week. What a terrible airline! Never use them.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

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.

The check in at the airport was awful. Told I need to pay for a bag. The item was taken at screening. I went back to get my $ back and they gave me a coupon with a QR code that doesn’t work. Worst costumer service ever!!!!!

4 hour delay because they used our aircraft to fly a different segment (per the captain)

Lost baggage on my connecting flight. 24 hours later, still no update on my bags.

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.
6/4Tue
2 stopsSpirit Airlines
15h 33mORD-OAK
$49
5/29Wed
1 stopSpirit Airlines
14h 04mORD-OAK
$54
5/26Sun
1 stopSun Country Air
16h 14mORD-OAK
$98
5/17Fri
2 stops
29h 55mORD-OAK
$108
6/1Sat
1 stopDelta
7h 27mORD-OAK
$118
8/6Tue
1 stopDelta
7h 50mMDW-OAK
$124
5/26Sun
2 stops
16h 29mORD-OAK
$125
6/9Sun
1 stopSun Country Air
22h 09mORD-OAK
$128
5/17Fri
1 stopAlaska Airlines
14h 40mORD-OAK
$256
6/5Wed
2 stopsAlaska Airlines
12h 46mORD-OAK
$262

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.
5/8Wed
multi-stopSpirit Airlines
8h 08mORD-OAK
5/14Tue
multi-stopSpirit Airlines
7h 01mOAK-ORD
$292
5/8Wed
multi-stopSpirit Airlines
14h 15mORD-OAK
5/15Wed
multi-stopSpirit Airlines
22h 10mOAK-ORD
$317
5/8Wed
multi-stopSpirit Airlines
8h 08mORD-OAK
5/11Sat
multi-stopSpirit Airlines
14h 35mOAK-ORD
$325
5/8Wed
multi-stopSpirit Airlines
8h 08mORD-OAK
5/11Sat
multi-stopSpirit Airlines
12h 48mOAK-ORD
$333
5/6Mon
multi-stopSpirit Airlines
6h 23mORD-OAK
6/17Mon
multi-stopSpirit Airlines
7h 15mOAK-ORD
$341
5/6Mon
multi-stopSpirit Airlines
6h 23mORD-OAK
6/17Mon
multi-stopSpirit Airlines
16h 11mOAK-ORD
$348
5/7Tue
multi-stopDelta
11h 36mMDW-OAK
5/11Sat
multi-stopDelta
9h 05mOAK-MDW
$423
5/5Sun
multi-stop
15h 04mORD-OAK
5/8Wed
multi-stop
9h 26mOAK-ORD
$677
5/7Tue
multi-stopDelta
11h 36mMDW-OAK
5/11Sat
multi-stopDelta
9h 05mOAK-MDW
$716
5/5Sun
multi-stopDelta
12h 40mMDW-OAK
5/12Sun
multi-stopDelta
9h 16mOAK-MDW
$926

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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
Flights5h 55m
Trains$4760h 00m