OAK - CHI

$129 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 8/12. 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
$267
Typical prices: $560-$456
Southwest
Tue 8/18Wed 8/19
OAK - MDW • 1 stop
Cheapest non-stop
$332
Typical prices: $680-$456
Southwest
Sun 8/16Wed 8/19
OAK - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
OAK's compact size ensures quick and easy navigation.
The CTA Orange Line from MDW is convenient for downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $292 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 05m
Direct flights
Direct flights
+1
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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 • 48% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
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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, Aug 18 - Wed, Aug 19
Southwest Logo
8:55 am - 7:10 pm
OAK
-
MDW
8h 15m
1 stop
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
OAK
4h 30mnonstop
$267Southwest
Tue, Aug 18 - Wed, Aug 19
Southwest Logo
6:15 am - 5:10 pm
OAK
-
MDW
8h 55m
2 stops
Southwest Logo
10:15 am - 12:40 pm
MDW
-
OAK
4h 25mnonstop
$272Southwest
Tue, Aug 4 - Tue, Aug 11
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$277Alaska Airlines
Tue, Jun 30 - Wed, Jul 15
Delta Logo
6:00 am - 5:02 pm
OAK
-
ORD
9h 02m
2 stops
Delta Logo
7:40 pm - 11:50 pm
ORD
-
OAK
6h 10m
1 stop
$282Delta
Tue, Aug 18 - Wed, Aug 19
Southwest Logo
6:15 am - 5:10 pm
OAK
-
MDW
8h 55m
2 stops
Southwest Logo
6:00 pm - 10:30 pm
MDW
-
OAK
6h 30m
1 stop
$282Southwest
Tue, Jun 30 - Tue, Jul 14
Delta Logo
6:00 am - 5:02 pm
OAK
-
ORD
9h 02m
2 stops
Delta Logo
11:30 am - 11:50 pm
ORD
-
OAK
14h 20m
2 stops
$288Delta
Wed, Jun 10 - Tue, Jun 16
Alaska Airlines Logo
10:37 am - 11:36 pm
OAK
-
ORD
10h 59m
1 stop
Alaska Airlines Logo
7:59 pm - 9:57 am
ORD
-
OAK
15h 58m
1 stop
$292Alaska Airlines
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
10:15 am - 7:50 pm
OAK
-
MDW
7h 35m
1 stop
Southwest Logo
2:40 pm - 7:00 pm
MDW
-
OAK
6h 20m
1 stop
$292Southwest
Sat, Jun 6 - Tue, Jun 9
Delta Logo
5:55 pm - 8:38 am
OAK
-
ORD
12h 43m
2 stops
Delta Logo
7:45 am - 11:53 am
ORD
-
OAK
6h 08m
1 stop
$297Delta
Mon, Jun 8 - Wed, Jun 10
Alaska Airlines Logo
2:58 pm - 11:55 pm
OAK
-
ORD
6h 57m
1 stop
Alaska Airlines Logo
2:20 pm - 10:41 pm
ORD
-
OAK
10h 21m
1 stop
$307Alaska Airlines
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 August.

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 $340 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$129
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Oakland to Chicago Midway 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 $129 for a one-way ticket and $292 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?

    JetBlue, American Airlines, Alaska 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 737-800 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 $418 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 $316 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 $238 or less one-way and $444 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 4 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 12384 reviews
8.1Boarding
7.0Food
7.0Entertainment
7.8Comfort
8.5Crew
Airline reviews

The gate agents begged us to check our carryons. They BEGGED us, over and over, and said that the flight was completely, totally full, and said that if we don't check our bags, it will cause huge delays. They finally said that "group suchandsuch will be required to check bags!" So I checked mine. Well, the flight wasn't close to being full, and many of the overhead compartments were *empty*! Moreover, my bag was delayed at the carousel, and it wasn't on the carousel that was posted. COME ON, AIRLINE, you can look at the seating for the flight on your computer and decide whether it's really necessary to beg and beg and beg people to go through the hassle of checking their bags! This is annoying as hell and makes me not want to use your crummy airline ever again.

4.0 OkayBryan, May 2026
SBP - SAN
Read more Alaska Airlines reviews

The gate agents begged us to check our carryons. They BEGGED us, over and over, and said that the flight was completely, totally full, and said that if we don't check our bags, it will cause huge delays. They finally said that "group suchandsuch will be required to check bags!" So I checked mine. Well, the flight wasn't close to being full, and many of the overhead compartments were *empty*! Moreover, my bag was delayed at the carousel, and it wasn't on the carousel that was posted. COME ON, AIRLINE, you can look at the seating for the flight on your computer and decide whether it's really necessary to beg and beg and beg people to go through the hassle of checking their bags! This is annoying as hell and makes me not want to use your crummy airline ever again.

Flight got delayed like 5 times, then they put and ada passenger in the back of the plane.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Flight delayed no communication. The gate was changed so many times.

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

It is a hassle to not have entertainment screens on the backs of the seats.

I had to cancel my trip due to medical reasons. I have been unable to cancel online through either Kayak or Alaska Airlines.. I am trying to get my insured trip reimbursed by XCover. They are requiring a notice of cancellation or not using to get my refund. Please help me get that information. I have been unable to get this information from either Kayak or Alaska Airlines.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

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!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Shut down without prior notice End up with spending lots of extra $$$

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

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

Information on your arrival and departure airports