CHI - OAK

$115 Find Cheap Flights from Chicago to Oakland - Compare and Save

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 12/8. 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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Everything you should know

Cheapest round-trip
$241
Southwest
Sat 8/22Mon 8/24
MDW - OAK • Non-stop
Cheapest non-stop
$237
Southwest
Wed 8/19Sat 8/29
MDW - OAK • Non-stop
Top airlines
Cheapest • from $237 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 4h 31m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
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Insights
Avoid delays
Most punctual • 70% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $319 (round-trip)
Shortest trip • 6h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 59% price drop
Most popular
Good to know
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+1
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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

Sat, Aug 22 - Mon, Aug 24
Southwest Logo
1:55 pm - 4:20 pm
MDW
-
OAK
4h 25mnonstop
Southwest Logo
5:20 am - 11:25 am
OAK
-
MDW
4h 05mnonstop
$241Southwest
Tue, Aug 11 - Sat, Aug 15
Southwest Logo
6:00 pm - 10:30 pm
MDW
-
OAK
6h 30m
1 stop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$247Southwest
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
OAK
4h 30mnonstop
Southwest Logo
8:55 am - 7:10 pm
OAK
-
MDW
8h 15m
1 stop
$251Southwest
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
5:30 am - 9:45 am
MDW
-
OAK
6h 15m
1 stop
Southwest Logo
8:30 pm - 5:45 am
OAK
-
MDW
7h 15m
1 stop
$252Southwest
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
10:15 am - 2:50 pm
MDW
-
OAK
6h 35m
1 stop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$255Southwest
Wed, Jul 29 - Tue, Aug 4
Alaska Airlines Logo
2:20 pm - 10:41 pm
ORD
-
OAK
10h 21m
1 stop
Alaska Airlines Logo
8:10 pm - 1:21 pm
OAK
-
ORD
15h 11m
1 stop
$257Alaska Airlines
Wed, Aug 5 - Mon, Aug 10
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
$261Alaska Airlines
Thu, Aug 6 - Thu, Aug 13
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
$265Alaska Airlines
Thu, Sep 24 - Sat, Oct 3
Delta Logo
1:55 pm - 11:59 pm
ORD
-
OAK
12h 04m
2 stops
Delta Logo
12:39 pm - 9:52 pm
OAK
-
ORD
7h 13m
1 stop
$270Delta
Mon, Dec 14 - Tue, Jan 5
Delta Logo
6:59 pm - 11:56 pm
ORD
-
OAK
6h 57m
1 stop
Delta Logo
1:15 pm - 9:53 pm
OAK
-
ORD
6h 38m
1 stop
$310Delta
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.

How much is a round-trip flight from Chicago to Oakland, California?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Oakland, California departing in August.

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 $294 on the route between Chicago Midway Airport (MDW) and Oakland (OAK). It is also the most popular route.

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 August, where tickets cost $83 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $288 and $275 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 $366 on average.

Expert advice

Expert advice for your flight from Chicago to Oakland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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.

Gabriel Leigh

Gabriel Leigh

Expert on OAK

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.

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 41% 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 5 days, the lowest price for a flight from Chicago to Oakland was $115 for a one-way ticket and $237 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, United Airlines, Hawaiian Airlines, Alaska Airlines, and Air Canada 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?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Oakland, with SkyTeam being the most commonly used for this 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, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and United Airlines. With an average price for the route of $413 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $469 and an overall rating of 7.4.

  • 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 $226 or less one-way and $294 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

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Sunday

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See more direct flights

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

10.0 ExcellentAnonymous, May 2026
PDX - OAK
Read more Southwest reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

Boarding was easy. The seats are small and fairly uncomfortable

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

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

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

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

Everything went well, but the flight was delayed multiple times. The delays were only minutes, but it was without information on why it was delayed.

Multiple delays, poor communication of information and a 4 hour delay with multiple gate changes ...

no entertainment options available on a 4+ hour flight. packed in like sardines. one bathroom. late flight.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Terrible, if possible won't be flying again anytime soon!

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.

A bit rush for transit. Food and entertainment are not available

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

My flight was delayed for a whole day, so I lost a day of my vacation.

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

Information on your arrival and departure airports