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CHI - OAK

$55 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 5/7. 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 5/27
Mon 6/3

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 44,335,567 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
4:05 pm - 10:55 pmORD-OAK
8h 50m1 stop
11:22 am - 6:00 amOAK-ORD
16h 38m1 stop
$115Spirit Airlines
Find Deal
Sat, May 11 - Tue, May 14
1:13 pm - 9:40 pmORD-OAK
10h 27m1 stop
11:22 am - 6:00 amOAK-ORD
16h 38m1 stop
$138Spirit Airlines
Find Deal
Wed, May 8 - Tue, May 14
10:57 pm - 8:52 amORD-OAK
11h 55m1 stop
12:02 pm - 9:55 pmOAK-ORD
7h 53m1 stop
$139Spirit Airlines
Find Deal
Tue, May 14 - Wed, May 22
10:57 pm - 6:52 amORD-OAK
9h 55m1 stop
11:59 pm - 7:06 pmOAK-ORD
17h 07m1 stop
Thu, May 30 - Thu, Jun 6
8:30 am - 10:44 pmORD-OAK
16h 14m1 stop
11:59 pm - 11:38 amOAK-ORD
9h 39m1 stop
$201Sun Country Air
Find Deal
Sun, May 26 - Thu, May 30
8:30 am - 10:44 pmORD-OAK
16h 14m1 stop
12:02 pm - 6:00 amOAK-ORD
15h 58m2 stops
Sun, May 26 - Wed, May 29
8:05 pm - 10:53 pmORD-OAK
28h 48m1 stop
11:59 pm - 7:16 pmOAK-ORD
17h 17m1 stop
$275Sun Country Air
Find Deal
Wed, Jun 12 - Thu, Jun 20
6:59 pm - 11:55 pmORD-OAK
6h 56m1 stop
10:45 pm - 8:22 amOAK-ORD
7h 37m1 stop
$278Delta
Find Deal
Fri, Sep 27 - Mon, Sep 30
1:05 pm - 9:35 pmMDW-OAK
10h 30m1 stop
10:45 pm - 12:31 pmOAK-MDW
11h 46m2 stops
$283Delta
Find Deal
Fri, Sep 27 - Mon, Sep 30
8:00 am - 11:00 amORD-OAK
29h 00m1 stop
6:00 am - 4:54 pmOAK-ORD
8h 54m1 stop
$291Alaska Airlines
Find Deal
Fri, May 31 - Mon, Jun 3

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 Monday, and avoid Sundays 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 ($55) and Sun Country Air ($111). The cheapest round-trip tickets were found on Spirit Airlines ($115) and Sun Country Air ($201).

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

Each day, there are between 1 and 2 nonstop flights that take off from Chicago and land in Oakland, California, with an average flight time of 4h 36m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 12 flights. The most frequent day of departure is Friday, when 17% 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 6:30 am and will be landing in Oakland, California at 9:10 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 9:35 pm and lands at 12:05 am.

Good to know

Low season

April

High season

March

Cheapest flight

$55
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 $55 for a one-way ticket and $115 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 $403 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 9115 reviews
7.9comfort
7.3entertainment
8.6crew
7.3food
8.2boarding
Airline reviews

I was seated at the back of the plane and the flight attendants were fantastic. I did not get food so can’t say. Thought the movie selection was lean.

10.0 ExcellentAnonymous, Apr 2024BOS - SAN
Read more about Alaska Airlines reviews

I was seated at the back of the plane and the flight attendants were fantastic. I did not get food so can’t say. Thought the movie selection was lean.

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

The messaging about the change in flight destination and options for getting to SFO was poor. There should have been frequent updates. When I spoke to the boarding agent moment before we were supposed to board, he was flippant and offered no help before the announcement was made that transportation would be arranged. It was as poor of an experience that I've ever had.

My plane ride down landed 20 min late. Boarding at SFO was strange too. The people at the terminal were nice—but, boarding lacked direction, and was confusing . Coming back was worse—the plane was hours behind—and I barely caught the last Bart train back to San Francisco (3 min more and I would have been in trouble). It was a very stressful trip, and it didn’t need to be.

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

The absolute coldest flight I’ve ever been on, even with a sweater and zip up sweatshirt. Was miserable the entire flight.

the departure got delayed due to SJC situation, but it was a quite good waiting thanks to Alaska airline teams.

The flight attendant in the back of the plane was barely understood as she rushed through instructions to the point of being intelligible. She had a bored demeanor in her delivery.

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

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.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

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.

It was my wife traveling so she ends up not traveling because they didn’t help her at the counter they blame it to the check in system at the airport and they told her if you want to travel in the other flight you have to pay $99 dollars and she will have to go to Las Vegas and then to Los Angeles almost 12 hours flight or to travel another day and we asked for a refund they said no refund and we called customer service and they didn’t help know she will travel the end of this week.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

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.
5/7Tue
2 stopsSpirit Airlines
14h 28mORD-OAK
$55
5/21Tue
1 stopSpirit Airlines
14h 20mORD-OAK
$61
5/26Sun
1 stopSun Country Air
16h 14mORD-OAK
$111
5/30Thu
1 stopDelta
6h 21mORD-OAK
$118
8/17Sat
1 stopDelta
9h 30mMDW-OAK
$118
7/5Fri
2 stops
26h 15mORD-OAK
$158
5/27Mon
3 stops
27h 40mORD-OAK
$177
6/8Sat
2 stopsAlaska Airlines
17h 59mORD-OAK
$184
7/7Sun
1 stopSun Country Air
22h 49mORD-OAK
$208
5/17Fri
2 stopsAlaska Airlines
17h 59mORD-OAK
$223

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.
4/30Tue
multi-stopSpirit Airlines
12h 04mORD-OAK
5/8Wed
multi-stopSpirit Airlines
14h 25mOAK-ORD
$269
5/2Thu
multi-stopSpirit Airlines
20h 55mORD-OAK
5/11Sat
multi-stopSpirit Airlines
13h 28mOAK-ORD
$309
5/2Thu
multi-stopSpirit Airlines
20h 55mORD-OAK
5/11Sat
multi-stopSpirit Airlines
14h 35mOAK-ORD
$311
5/1Wed
multi-stop
10h 49mORD-OAK
5/2Thu
multi-stop
18h 49mOAK-ORD
$447
5/1Wed
multi-stop
15h 39mORD-OAK
5/2Thu
multi-stop
18h 49mOAK-ORD
$450
4/27Sat
multi-stopDelta
11h 39mMDW-OAK
4/29Mon
multi-stopDelta
13h 10mOAK-MDW
$570
4/27Sat
multi-stopDelta
12h 09mMDW-OAK
5/1Wed
multi-stopDelta
13h 14mOAK-MDW
$709
4/30Tue
multi-stopAlaska Airlines
29h 22mORD-OAK
5/8Wed
multi-stopAlaska Airlines
17h 50mOAK-ORD
$734
4/27Sat
multi-stopVolaris
15h 38mMDW-OAK
5/1Wed
multi-stopVolaris
16h 15mOAK-MDW
$1,087
4/27Sat
multi-stopVolaris
25h 51mMDW-OAK
4/29Mon
multi-stopVolaris
13h 08mOAK-MDW
$1,513

Search by stops

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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
Flights6h 56m
Trains$3450h 00m