OAK - CHI

$59 Find Cheap Flights from Oakland to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Chicago departing on 5/29. 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.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Chicago, as well as popular online travel agencies
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Cheap Flights from Oakland to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Chicago 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.

Recent round-trip flight deals from Oakland to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Oakland to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
10:36 am - 5:25 amOAK-ORD
16h 49m2 stops
Spirit Airlines Logo
11:50 am - 8:14 pmORD-OAK
10h 24m1 stop
$138Spirit Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
Spirit Airlines Logo
9:09 pm - 10:55 amOAK-ORD
11h 46m1 stop
Spirit Airlines Logo
11:50 am - 8:14 pmORD-OAK
10h 24m1 stop
$139Spirit Airlines
Find Deal
Mon, Jun 2 - Mon, Jun 9
Hawaiian Airlines Logo
12:48 pm - 11:59 pmOAK-ORD
9h 11m1 stop
Hawaiian Airlines Logo
6:00 am - 12:08 pmORD-OAK
8h 08m1 stop
$206Hawaiian Airlines
Find Deal
Wed, May 28 - Sat, May 31
Alaska Airlines Logo
12:48 pm - 10:23 pmOAK-ORD
7h 35m1 stop
Alaska Airlines Logo
6:00 am - 1:36 pmORD-OAK
9h 36m1 stop
$216Alaska Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 10
Southwest Logo
9:15 pm - 5:00 amOAK-MDW
5h 45m1 stop
Southwest Logo
7:50 am - 12:05 pmMDW-OAK
6h 15m1 stop
$227Southwest
Find Deal
Mon, Jun 30 - Sat, Jul 12
Southwest Logo
2:05 pm - 11:40 pmOAK-ORD
7h 35m1 stop
Southwest Logo
12:40 pm - 10:45 pmORD-OAK
12h 05m1 stop
$232Southwest
Find Deal
Mon, Jun 30 - Sat, Jul 12
Hawaiian Airlines Logo
7:00 am - 6:55 pmOAK-ORD
9h 55m1 stop
Hawaiian Airlines Logo
6:00 am - 12:08 pmORD-OAK
8h 08m1 stop
$240Hawaiian Airlines
Find Deal
Tue, May 20 - Sat, May 31
Delta Logo
12:30 pm - 10:08 pmOAK-ORD
7h 38m1 stop
Delta Logo
7:20 pm - 11:55 pmORD-OAK
6h 35m1 stop
$257Delta
Find Deal
Wed, Jul 23 - Wed, Jul 30
Delta Logo
4:58 pm - 7:49 amOAK-ORD
12h 51m2 stops
Delta Logo
7:20 pm - 11:55 pmORD-OAK
6h 35m1 stop
$262Delta
Find Deal
Tue, Jul 22 - Tue, Jul 29
Alaska Airlines Logo
12:49 pm - 10:30 pmOAK-ORD
7h 41m1 stop
Alaska Airlines Logo
6:00 am - 12:09 pmORD-OAK
8h 09m1 stop
$276Alaska Airlines
Find Deal
Tue, Jul 22 - Fri, Aug 15
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KAYAK's insights & trends for Oakland to Chicago flights

Get data-powered insights and trends into flights from Oakland to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Oakland to Chicago flight route?

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

Our data shows that the cheapest route for a return flight from Oakland to Chicago cost $327 and was between Oakland (OAK) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $327.

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

The average price of all round-trip flights from Oakland to Chicago clicked on KAYAK for each day over the last 12 months.

For Oakland to Chicago, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to Oakland, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Chicago, 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 Oakland to Chicago is April, where tickets cost $96 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $393 and $391 respectively.

Can I save money by flying with a layover from Oakland to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $258, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Oakland to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Oakland to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonFebruary
High seasonApril
Cheapest flight$59
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 70% lower on average.
Flight from Oakland to Chicago O'Hare Airport

When to book flights from Oakland to Chicago

Are your dates flexible? Find out the best times to travel from Oakland to Chicago 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 Oakland to Chicago

  • Are there nursing rooms at MDW?

    MDW has a nursing room in Concourse C, next to the yoga room. This room, well-furnished with comfy seats, features a hand washing station and clean utensils. If you're a breastfeeding mother, you can use this nursing room to breastfeed and change your infant privately before continuing your journey.

  • Does OAK have any fun places I can visit?

    While waiting for your flight to Chicago at OAK, you should check out the airport's public art displays in Terminal 2, near the baggage claim area, and in Terminal 1, on the Airside. Additionally, there are a variety of retail shops throughout both terminals you can check out.

  • Which Chicago Airport has an on-site hotel?

    If you'd like to land at a Chicago airport with an on-site hotel, you should book a flight that lands at ORD, as this public transit hub is home to two on-site hotels, Hilton Chicago O'Hare Airport Hotel and Aloft Chicago O'Hare. Hilton Chicago O'Hare Airport Hotel is located opposite Terminal 2. It is connected to all the airport terminals via an underground Walkway. Aloft Chicago O'Hare is located between Terminals 1, 2, and 3. Since both hotels feature great amenities, staying at either would be a move you'll not regret.

  • Does OAK have any lounges?

    Oakland International Airport has a lounge in Terminal 1, on the Airside, near Gates 8 and 8A. This relaxing space, referred to as the Escape lounge, is open to all economy travelers at the airport. If you're one, you can access it if you're open to purchasing a day pass, annual membership, or pay at the door.

  • What is the cheapest flight from Oakland to Chicago?

    In the last 3 days, the lowest price for a flight from Oakland to Chicago was $59 for a one-way ticket and $138 for a round-trip.

  • Do I need a passport to fly between Oakland and Chicago?

    No, a passport isn't needed to fly from Oakland to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Oakland to Chicago?

    Oakland is served by only 1 airport and there are 2 airports in Chicago. You will leave Oakland from Oakland and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Oakland to Chicago?

    American Airlines, JetBlue, Alaska Airlines, Hawaiian Airlines, and Delta offer inflight Wi-Fi service on the Oakland to Chicago flight route.

  • Which aircraft models fly most regularly from Oakland to Chicago?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Oakland to Chicago flight route.

  • On which days can I fly direct from Oakland to Chicago?

    There are nonstop flights from Oakland to Chicago on a daily basis.

  • Which is the best airline for flights from Oakland to Chicago, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Oakland to Chicago are Southwest and Alaska Airlines. With an average price for the route of $398 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $346 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Oakland to Chicago?

    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 Oakland to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Oakland 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 Oakland to Chicago?

    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 Chicago with an airline and back to Oakland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Chicago?

    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 Chicago from Oakland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Oakland to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $208 or less one-way and $387 or less round-trip.
  • In Oakland, you can board your plane to Chicago at Norman Y. Mineta San Jose International Airport (SJC), Oakland International Airport (OAK), or San Francisco International Airport (SFO). Among the three airports, OAK has the smallest crowds. It is also the nearest to Oakland. Given its proximity to Oakland and its small passenger crowds, OAK is the most convenient Oakland airport to fly out to Chicago.
  • You can travel to OAK from downtown Oakland through three public means of transit. They include the subway, bus, and taxi. The means you choose will be determined by how fast you'd like to travel and how much you are willing to spend as fare. If you'd like to travel cheaply, you should travel by subway or bus. However, if you'd like to travel quickly, you should travel by taxi.
  • If you drive to OAK, you can count on easily finding a spot you can leave your car in for the entire duration of your trip, as OAK is home to four on-airport parking options that offer long-term parking services. Premium, Hourly, Daily, and Economy are located in different parts of the airport. Premium is the closest of the four, as it is situated adjacent to the terminals.
  • In Chicago, you can land at either O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). ORD usually has more passenger traffic than MDW. Hence, it normally has long queues. This being the case, to avoid long queues once you land, you should book a flight from Chicago that lands at MDW.
  • Once you land at ORD or MDW, there are several towns you can get to easily, other than Chicago. They include Elmhurst, Aurora, Gurnee, Dundee, New Buffalo, and Lake Geneva.

Prefer to fly direct from Oakland to Chicago?

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

Direct departures

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

Direct returns

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
See more direct flights

Top 5 airlines serving from Oakland to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Chicago. 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 Oakland to Chicago? 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 9968 reviews
7.1Food
8.2Boarding
8.5Crew
7.1Entertainment
7.9Comfort
Airline reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

2.0 MediocreAnonymous, Apr 2025SNA - PDX
Read more Alaska Airlines reviews

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

Check your emails that you sent me. 9 emails were sent telling me that my flight is Delayed. Each one with a different time 7:10, 7:55, 9:31, 9:09, 9:29, 9:44, 10:00, 9:49, and 10:10. That was how my experience went.

It was my first time flying Alaska Airlines and first time flying from Santa Rosa airport. The staff was very professional and friendly. Their instructions were clear and any question was answered satisfactorily. My seat was comfortable and the in-flight beverage service very adequate for the duration of the flight. We arrived ahead of the scheduled landing time and deplaning was simple. I look forward to flying with Alaska again.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

No non-alcoholic drinks available except water and small apple juice cans.

Flight attendant took my carefully folded coat and flung it across the aisle to the bin across the way. Where one of the passengers rescued it for me, because that just wasn’t right!!

First time flying with any airline that has decent seating. Great experience crew was friendly and the pilot was as well.

The flight was delayed by 3 hours and 30 minutes without any explanation.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

Doubt that you care, the flight from OAK to Las Vegas took longer on the runway when we arrived. The flight attendants & pilot announced that they knew a lot of us were getting on a connection to Dallas & that it was waiting for us. Lied. Ended up having to take another layover & it’s added way more time to my flights. The ticketing staff at the gates were extremely rude. I don’t think I ever want to fly Spirit again.

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