OAK - CHI

$165 Find Cheap Flights from Oakland to Chicago - 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 Oakland to Chicago departing on 7/6. 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 Chicago

 
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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Everything you should know

Cheapest round-trip
$352
Typical prices: $388-$234
Alaska Airlines, Frontier
Tue 7/21Mon 9/21
OAK - ORD • 1 stop
Cheapest non-stop
$353
Typical prices: $680-$513
Southwest
Fri 8/7Mon 8/10
OAK - MDW • Non-stop
Top airlines
Cheapest • from $353 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $236 (round-trip)
Shortest trip • 6h 00m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 54% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Expert advice
Flight Deals

Cheap Flights from Oakland to Chicago (OAK-CHI)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oakland to Chicago

Tue, Jul 21 - Mon, Sep 21
Multiple Airlines Logo
5:35 pm - 5:00 am
OAK
-
ORD
9h 25m
1 stop
Multiple Airlines Logo
6:50 am - 7:44 pm
ORD
-
OAK
14h 54m
1 stop
$352Multiple Airlines
Fri, Aug 7 - Mon, Aug 10
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
OAK
4h 30mnonstop
$353Southwest
Fri, Jul 17 - Tue, Jul 21
Southwest Logo
4:00 pm - 12:20 am
OAK
-
MDW
6h 20m
1 stop
Southwest Logo
10:00 am - 12:30 pm
MDW
-
OAK
4h 30mnonstop
$354Southwest
Wed, Jul 8 - Wed, Jul 15
Alaska Airlines Logo
7:52 am - 5:00 am
OAK
-
ORD
19h 08m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$355Alaska Airlines
Sat, Jul 11 - Sat, Jul 18
Southwest Logo
8:25 pm - 4:40 am
OAK
-
MDW
6h 15m
1 stop
Southwest Logo
12:15 pm - 5:10 pm
MDW
-
OAK
6h 55m
1 stop
$355Southwest
Wed, Jul 8 - Tue, Jul 14
Southwest Logo
5:15 am - 2:35 pm
OAK
-
MDW
7h 20m
2 stops
Southwest Logo
5:30 am - 9:45 am
MDW
-
OAK
6h 15m
1 stop
$356Southwest
Wed, Sep 16 - Mon, Sep 21
Multiple Airlines Logo
3:13 pm - 1:22 pm
OAK
-
ORD
20h 09m
1 stop
Multiple Airlines Logo
6:50 am - 7:44 pm
ORD
-
OAK
14h 54m
1 stop
$358Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
Delta Logo
12:39 pm - 10:02 pm
OAK
-
ORD
7h 23m
1 stop
Delta Logo
5:10 pm - 11:59 pm
ORD
-
OAK
8h 49m
2 stops
$360Delta
Fri, Jul 10 - Sat, Jul 18
Alaska Airlines Logo
7:13 pm - 5:00 am
OAK
-
ORD
7h 47m
1 stop
Alaska Airlines Logo
5:59 pm - 10:41 pm
ORD
-
OAK
6h 42m
1 stop
$364Alaska Airlines
Sat, Oct 24 - Thu, Oct 29
Delta Logo
5:05 pm - 10:07 am
OAK
-
ORD
15h 02m
2 stops
Delta Logo
7:05 am - 4:32 pm
ORD
-
OAK
11h 27m
2 stops
$366Delta
Booking Insights

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.

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

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

What is the cheapest Oakland to Chicago flight route?

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

The cheapest return flight from Oakland to Chicago costs $348 on the route between Oakland (OAK) and Chicago Midway Airport (MDW). It is also the most popular route.

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 $93 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $274 and $271 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $421 on average.

Expert advice

Expert advice for your flight from Oakland to Chicago

 
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 seasonFebruary
Cheapest flight$165
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 12% 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 5 days, the lowest price for a flight from Oakland to Chicago was $156 for a one-way ticket and $352 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, Delta, and Hawaiian Airlines offer inflight Wi-Fi service on the Oakland to Chicago flight route.

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

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Oakland to Chicago flight route.

  • Which airline alliances offer flights from Oakland to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Oakland and Chicago, with Star Alliance being the most commonly used for this 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 $419 and an overall rating of 7.9, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $354 and an overall rating of 7.9.

  • 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 $231 or less one-way and $458 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying 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

Reviews of the top 3 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.
7.9
Alaska AirlinesOverall score based on 12533 reviews
8.5Crew
7.8Comfort
8.1Boarding
7.0Food
7.0Entertainment
Airline reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

2.0 MediocreJane, Jun 2026
SMF - SEA
Read more Alaska Airlines reviews

Subject: Formal Complaint – Incompetent Service and Denied Boarding on Flight 1409 (CLSVJM – Dear Alaska Airlines Customer Relations, I am writing to file a formal complaint regarding my experience on Flight 1409 departing from Seattle on 6/13/26. As a physician and business owner who frequently coordinates group travel, this was one of the worst airline experiences I have encountered. Upon arrival, I was informed that my check-in boarding pass was not official, despite successfully obtaining it electronically through your website/app with no warnings or indications of issues. My electronic boarding pass was rejected, leading to cancellation/denial of boarding. The gate agent (an older woman) was unhelpful, claimed my name had been announced multiple times (which it had not—she did not even know my name correctly), and mistakenly boarded my traveling companion under my name. Additionally, an older blonde staff member nearly failed to return my passport, highlighting a clear lack of training on your check-in and boarding systems. This chaos forced me onto a later flight while my group waited in Canada, unable to check into our Airbnb or pick up rental cars (as I was the primary booker). The entire incident caused significant business disruption, stress, and additional expenses. I have flown Alaska Airlines previously but will not consider it again without resolution. I request: • Full reimbursement of any additional costs incurred. • Appropriate compensation (vouchers/miles) for the inconvenience and poor service. • Confirmation of corrective actions for Please respond within 7-10 business days. Sincerely, Dr. Chunwen Teng

Never had so many staff members be rude and disrespectful. I had a staff member sarcastically call me “girly” after making me wait 20 minutes to be seen by her. I was able to print my luggage tag and she told me I was too late to check luggage I said the system obviously disagrees. And you had me wait way too long while you asked every single passenger ahead of me about their Disney vacations. She wasted so much time to then say “girly your bag won’t make it on the plane” I’m not her girly I’m a full grown adult. She needs to learn a hell of a lot of respect

My flight was several times rescheduled and then finally canceled.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Flying into PAE was so easy because it’s baggage claim is quick and accesible. I had a car rental and the counter is inside the baggage claim area, very convenient.

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

The first flight was fine, great crew, but the plane was delayed 45 minutes to go to Seattle because of they were missing a ramp. That would make sense if the plane was actually at the gate. Not if we’re still waiting for a plane. After we landed we waited 30-45 minutes on the tarmac just to get off the plane. Alaska made me miss my connecting flight, wasting my time, and my money. I should honestly be reimbursed, but hey, when does the airline ever actually take accountability? Never.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Short trip, was nice to have a drink on the short flight still.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

Was fine, delayed and feels like southwest is always late

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

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

Information on your arrival and departure airports