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CHI - OAK

$77 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 9/10. 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
Fri 7/12
Fri 7/19

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 44,148,666 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
1:14 pm - 9:57 pmORD-OAK
10h 43m1 stop
5:20 am - 6:03 pmOAK-ORD
10h 43m1 stop
$161Spirit Airlines
Find Deal
Wed, Aug 21 - Wed, Sep 11
10:01 pm - 10:23 amORD-OAK
14h 22m1 stop
10:05 pm - 6:36 amOAK-ORD
6h 31m1 stop
$170Spirit Airlines
Find Deal
Tue, Jul 9 - Tue, Jul 16
6:55 pm - 7:51 pmORD-OAK
26h 56m2 stops
5:15 am - 2:43 pmOAK-ORD
7h 28m1 stop
Tue, Jul 9 - Tue, Jul 16
6:30 pm - 11:24 amORD-OAK
18h 54m2 stops
9:21 pm - 6:36 amOAK-ORD
7h 15m1 stop
Thu, Jul 4 - Mon, Jul 8
8:05 pm - 5:27 pmORD-OAK
23h 22m1 stop
5:45 pm - 7:59 pmOAK-ORD
24h 14m1 stop
$239Sun Country Air
Find Deal
Wed, Jul 24 - Sun, Jul 28
5:00 pm - 4:47 pmORD-OAK
25h 47m1 stop
11:59 pm - 6:19 pmOAK-ORD
16h 20m1 stop
$249Sun Country Air
Find Deal
Wed, Jul 10 - Sun, Jul 21
3:47 pm - 9:41 pmMDW-OAK
7h 54m1 stop
6:00 am - 6:38 pmOAK-MDW
10h 38m2 stops
$302Delta
Find Deal
Thu, Aug 15 - Mon, Aug 19
2:49 pm - 11:51 pmMDW-OAK
11h 02m2 stops
10:52 pm - 12:42 pmOAK-MDW
11h 50m2 stops
$307Delta
Find Deal
Fri, Aug 2 - Mon, Aug 5
6:00 am - 9:30 pmMDW-OAK
17h 30m2 stops
11:30 pm - 12:51 pmOAK-MDW
11h 21m1 stop
$614Frontier
Find Deal
Wed, Oct 2 - Sun, Oct 6
5:55 am - 9:30 pmMDW-OAK
17h 35m2 stops
11:59 pm - 7:28 pmOAK-MDW
17h 29m2 stops
$874Frontier
Find Deal
Wed, Jun 26 - Wed, Jun 26

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 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.
Our data shows that the cheapest route for a one-way flight from Chicago to Oakland cost $138 and was between Chicago Midway Airport and Oakland. 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 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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for 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 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 $356 respectively.

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 ($77) and Sun Country Air ($98). The cheapest round-trip tickets were found on Spirit Airlines ($161) and Sun Country Air ($239).

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

Each day, there are between 2 and 6 nonstop flights that take off from Chicago and land in Oakland, with an average flight time of 4h 28m. The most common departure time is 5:00 am and most flights take off in the afternoon. Each week, there are 29 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

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

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 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 jets off at 10:40 pm and lands at 1:10 am.

Good to know

Low season

February

High season

May

Cheapest flight

$77
Best time to beat the crowds with an average 46% drop in price.
Most popular time to fly with an average 13% 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?

    In the last 3 days, the lowest price for a flight from Chicago to Oakland was $77 for a one-way ticket and $161 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 $437 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 9269 reviews
7.3Entertainment
7.9Comfort
7.3Food
8.2Boarding
8.6Crew
Airline reviews

It was an okay experience overall. But, I’m quite tall and sitting in those seats was horrific and so uncomfortable. The flight attendants were quite rude when enforcing the procedures for take off and landing.

6.0 GoodAnonymous, Jun 2024EWR - LAX
Read more about Alaska Airlines reviews

It was an okay experience overall. But, I’m quite tall and sitting in those seats was horrific and so uncomfortable. The flight attendants were quite rude when enforcing the procedures for take off and landing.

It was cancelled due to crew. I missed a special family graduation due to this

I had never flown Alaska Airlines before. I’ll definitely use them again. Seats were comfortable and roomier than expected.

Seats lack shoulder and elbow room. The lady next to me was short and slightly heavy with knee problems, she kept jabbing me with her elbow while playing her game on her phone for 2 hours, the duration of the whole flight. It was frustrating and annoying! I was in the middle seat, there was no space to adjust to avoid her arm jabbing me.

I like the big picture of the Eskimo on the tail of the plane.

Being seated next to the engine was awful! I was nauseous the entire trip from pre-take-off, flying to landing. The engine vibration was very strong!

The crew was the best I’ve had the experience of flying with. A misbehaving child was making things difficult for me with bopping my tray table, taking my snack, and continually tapping or bumping me. The crew quietly and respectfully moved me to another seat, and thanked me for my patience. They couldn’t have been more kind. Their professionalism really stood out to me and I am more than happy to leave a great review for them!

I would have appreciated notification that our flight was moved to another gate LAST MINUTE so that we would not have missed it. We got no such notice and had to spend another night to catch an available flight in the morning, which was huge inconvenience. We will never fly Alaska again.

Flight was delayed 2 hours. It was too cold inside the cabin. My seat mate had no jacket so she was shivering the entire flight. The stewardess says there’s no available blanket.

The airline was way too cold. We were freezing, I don’t know if that is normal. Overall it was pretty good flight. Always flown Alaska Airlines and I am not changing.

It was very cold because the air conditioner was on high power, and my son got sick.

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

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.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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.

Poor response to delay, getting on plane, off plane and back on again

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was good and clean but delayed over an hour on the return flight.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

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

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

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

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.
9/10Tue
1 stopSpirit Airlines
9h 26mORD-OAK
$77
6/25Tue
1 stopSpirit Airlines
15h 11mORD-OAK
$85
7/18Thu
1 stopSun Country Air
12h 07mORD-OAK
$98
7/9Tue
2 stops
28h 05mORD-OAK
$101
7/8Mon
2 stops
28h 37mORD-OAK
$114
7/4Thu
1 stopDelta
9h 09mORD-OAK
$118
7/10Wed
1 stopDelta
7h 44mMDW-OAK
$118
6/19Wed
1 stopSun Country Air
28h 48mORD-OAK
$208
7/23Tue
2 stopsAlaska Airlines
19h 20mORD-OAK
$267
7/6Sat
1 stopAlaska Airlines
26h 12mORD-OAK
$282

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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.
6/17Mon
multi-stopSpirit Airlines
24h 57mORD-OAK
6/18Tue
multi-stopSpirit Airlines
22h 18mOAK-ORD
$283
6/17Mon
multi-stopSpirit Airlines
12h 14mORD-OAK
6/19Wed
multi-stopSpirit Airlines
7h 02mOAK-ORD
$289
6/17Mon
multi-stopSpirit Airlines
23h 49mORD-OAK
6/18Tue
multi-stopSpirit Airlines
22h 18mOAK-ORD
$293
6/17Mon
multi-stopSpirit Airlines
23h 49mORD-OAK
6/19Wed
multi-stopSpirit Airlines
7h 02mOAK-ORD
$303
6/17Mon
multi-stopSpirit Airlines
24h 57mORD-OAK
6/19Wed
multi-stopSpirit Airlines
16h 35mOAK-ORD
$308
6/16Sun
multi-stop
29h 47mORD-OAK
7/16Tue
multi-stop
10h 14mOAK-ORD
$336
6/16Sun
multi-stop
29h 47mORD-OAK
7/16Tue
multi-stop
15h 23mOAK-ORD
$357
6/13Thu
multi-stopDelta
6h 17mORD-OAK
6/16Sun
multi-stopDelta
10h 55mOAK-ORD
$655
6/13Thu
multi-stopDelta
13h 33mORD-OAK
6/16Sun
multi-stopDelta
10h 55mOAK-ORD
$660
6/16Sun
multi-stopFrontier
15h 04mORD-OAK
6/18Tue
multi-stopFrontier
24h 09mOAK-ORD
$1,014

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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 17m
Trains$5190h 00m