CHI - OAK

$110 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 1/24. 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
1 adult, Economy, 0 bags

KAYAK searches 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, 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 Chicago to Oakland, as well as popular online travel agencies
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Oakland

Wed, Dec 10 - Thu, Jan 8
Delta Logo
7:20 am - 11:50 amORD-OAK
6h 30m1 stop
Delta Logo
12:38 pm - 9:52 pmOAK-ORD
7h 14m1 stop
$261Delta
Find Deal
Sat, Dec 13 - Thu, Jan 8
Delta Logo
7:20 am - 11:50 amORD-OAK
6h 30m1 stop
Delta Logo
5:55 am - 5:21 pmOAK-ORD
9h 26m2 stops
$266Delta
Find Deal
Sat, Dec 13 - Thu, Jan 8
Delta Logo
3:00 pm - 10:00 pmORD-OAK
9h 00m2 stops
Delta Logo
5:55 am - 5:21 pmOAK-ORD
9h 26m2 stops
$271Delta
Find Deal
Wed, Jan 14 - Tue, Jan 20
Alaska Airlines Logo
6:06 pm - 8:40 pmORD-OAK
28h 34m1 stop
Alaska Airlines Logo
11:43 am - 11:55 pmOAK-ORD
10h 12m1 stop
$272Alaska Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
Alaska Airlines Logo
5:53 pm - 11:59 pmORD-OAK
8h 06m1 stop
Alaska Airlines Logo
6:30 am - 6:22 amOAK-ORD
21h 52m1 stop
$283Alaska Airlines
Find Deal
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
6:15 pm - 11:15 pmORD-OAK
7h 00m1 stop
Southwest Logo
5:15 am - 2:05 pmOAK-ORD
6h 50m1 stop
$286Southwest
Find Deal
Thu, Jan 15 - Tue, Jan 20
Alaska Airlines Logo
8:00 am - 7:23 pmORD-OAK
13h 23m2 stops
Alaska Airlines Logo
11:43 am - 11:55 pmOAK-ORD
10h 12m1 stop
$288Alaska Airlines
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
2:05 pm - 4:45 pmMDW-OAK
4h 40mnonstop
Southwest Logo
7:55 am - 4:10 pmOAK-MDW
6h 15m1 stop
$308Southwest
Find Deal
Sat, Dec 13 - Tue, Jan 6
Southwest Logo
2:05 pm - 4:45 pmMDW-OAK
4h 40mnonstop
Southwest Logo
11:10 am - 5:15 pmOAK-MDW
4h 05mnonstop
$310Southwest
Find Deal
Tue, Dec 16 - Sat, Jan 10
Southwest Logo
12:05 pm - 6:05 pmMDW-OAK
8h 00m2 stops
Southwest Logo
5:55 am - 12:00 pmOAK-MDW
4h 05mnonstop
$313Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Chicago Midway offers shorter security lines than ORD.
From OAK, Uber or Lyft are convenient transport options.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $261 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-OAK
Cheapest
MDW-OAK
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 31% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$261
Overall average: $445
Delta
Wed 12/10Thu 1/8
ORD - OAK • 1 stop
Cheapest non-stop
$310
Southwest
Sat 12/13Tue 1/6
MDW - OAK • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Oakland!
Booking Insights

KAYAK's insights & trends for Chicago to Oakland flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Oakland costs $301 on the route between Chicago Midway Airport (MDW) and Oakland (OAK). It is also the most popular route.

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

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

If your flying dates are flexible, you should consider flying to Oakland on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Oakland. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best 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 round-trip 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 September, where tickets cost $252 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $497 and $475 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $536 on average.

Expert advice

Expert advice for your flight from Chicago to Oakland

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

MDW offers a user-friendly experience with shorter security lines than ORD, making it ideal for domestic flights.

Read more about MDWby Stefanie Waldek
OAK

For transport from OAK, Uber or Lyft are recommended, but BART is a cheaper option during rush hour.

Read more about OAKby Gabriel Leigh
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on OAK

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Good to know

Low seasonApril
Cheapest flight$110
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 8% lower on average.
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 $110 for a one-way ticket and $261 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 airlines offer Wi-Fi service onboard planes from Chicago to Oakland?

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

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

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

  • Which airline alliances offer flights from Chicago to Oakland?

    Star Alliance is the only airline alliance operating flights between Chicago and Oakland.

  • 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, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and Alaska Airlines. With an average price for the route of $380 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 $552 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $306 or less one-way and $504 or less round-trip.
  • 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.

Prefer to fly direct from Chicago to Oakland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Oakland.
Find which airlines fly direct from Chicago to Oakland Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the top 4 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 11194 reviews
7.8Comfort
8.5Crew
7.1Food
7.0Entertainment
8.1Boarding
Airline reviews

Waiting 2 hours after landing to arrive at a gate was ridiculous.

4.0 OkayJack, Oct 2025DEN - SAN
Read more Alaska Airlines reviews

Waiting 2 hours after landing to arrive at a gate was ridiculous.

Almost 3 hr delay in Settle with very little information available to passengers. They boarded the plane and we waited for a long time inside the plane as well.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

I was a pilot with EAL so my input maters more than the average traveler. The crew at the ticket counter were amazing. I was traveling with a frozen 20 pound turkey from our farm in Oxford Florida and they were over the top in helping me get through TSA. The gate personnel were likewise accommodating. You and Jet Blue are my favorite airlines . Would love to do an add for Alaska Airlines. Nels Siverson

Online check in didn't work. Somehow ended up with 2 Alaska rewards numbers and 1 for Hawaiian. No one at check in could figure out what to do. No one at check in could help me confirm an upcoming flight on Hawaiian Airlines.

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

The flight was fine, but the Kayak app is terrible. I could not input my flight. I couldn’t use it for anything and it would not even let me try to add a seat once you purchased the ticket you might as well. Delete the Kayak app as far as I’m concerned. I’m done with kayak. Com

My flight got canceled never left san diego and miss out my fam event

Food and entertainment not applicable - standard drinks and cinnamon cookies; crew did not do a song and dance for us so no entertainment. I like the slightly better leg room than American Airlines - at least it felt that way. Flight crew and atmosphere seemed more welcoming than American, too.

this was the THIRD time in four Alaska flights that were 2 hours late. Only one was due to weather. The intentionally posted each flight as only 1 hour and 55 minutes late so that they wouldn't have to give out vouchers. And then the flights all ended up more than 2 hours late. Makes United look like a premium carrier.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Connecting flight is on time and boarding was a breeze!

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

I was never aware that I had to pay $100 per luggage to them on the plane that are simply carry-ons. This is discriminatory and I’m going to be alerting my entire family and friends and my Instagram following up over 75,000 of this issue and misunderstanding, including mismanaging.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Everything you need to know for your flight from Chicago to Oakland

Information on your arrival and departure airports

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