OAK - CHI

$101 Find Cheap Flights from Oakland to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Chicago departing on 5/16. 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
$217
Overall average: $371
Alaska Airlines
Tue 4/28Wed 4/29
OAK - ORD • 1 stop
Cheapest non-stop
$223
Typical prices: $307-$619
Southwest
Wed 4/15Sat 4/18
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 $217 (round-trip)
Best reviews • 8.0 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 02m
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 $245 (round-trip)
Shortest trip • 5h 50m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Apr 28 - Wed, Apr 29
Alaska Airlines Logo
6:46 am - 7:03 pm
OAK
-
ORD
10h 17m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$217Alaska Airlines
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
$223Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:30 pm - 9:45 pm
MDW
-
OAK
6h 15m
1 stop
$233Southwest
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
$234Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
10:00 am - 12:35 pm
MDW
-
OAK
4h 35mnonstop
$237Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
10:15 am - 4:55 pm
MDW
-
OAK
8h 40m
2 stops
$238Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$241Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$243Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
6:35 am - 3:00 pm
OAK
-
ORD
6h 25m
1 stop
Southwest Logo
7:00 am - 12:25 pm
ORD
-
OAK
7h 25m
1 stop
$243Southwest
Wed, May 6 - Mon, May 11
Alaska Airlines Logo
7:19 pm - 11:43 pm
OAK
-
ORD
26h 24m
1 stop
Alaska Airlines Logo
7:59 pm - 6:39 pm
ORD
-
OAK
24h 40m
1 stop
$249Alaska 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 April.

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 $257 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 July, where tickets cost $277 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $631 and $609 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 1 stop layover the cheapest option at $398 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$101
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 24% 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 $101 for a one-way ticket and $217 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, 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 MAX 8 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 8.0, 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 8.0.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Oakland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oakland to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Oakland with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Oakland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $216 or less one-way and $332 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.
8.0
Alaska AirlinesOverall score based on 12030 reviews
8.5Crew
8.1Boarding
7.1Food
7.0Entertainment
7.8Comfort
Airline reviews

signage from the upper area to the tram down 2 escalator!

8.0 ExcellentAnonymous, Mar 2026
PSP - SEA
Read more Alaska Airlines reviews

signage from the upper area to the tram down 2 escalator!

You sent me an email saying boarding was at 9:29 and AA sent one that was 8:29 on Sunday morning. I had to call AA to get that it was indeed 8:29.

Not bad. Due to not buying a seat, on the way back, my seat was not assigned till 2 hrs before the flight left. Got me worried I wouldn’t have a seat.

Great flights, little turbulence, pilots kept stewardesses seated & safe, all staff friendly & professional

There is no entertainment on the plane. The snack is minimal. The crew was nice and professional.

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

This was my first trip with Alaska Airlines (round trip DCA to San Diego). Despite a slight delay on the return flight, I feel compelled to post a RAVE review! I cannot praise the airline and the crew enough! Everyone was kind, professional, and courteous, every step of the way- excellent service, snacks, and entertainment! On both legs of the trip I inquired whether there were any free seating upgrades and my request were granted BOTH times! I’ve flown on other airlines where they won’t do that, even when those premium seats are empty. As a customer service professional myself, I can say I left my experience feeling like a valued customer and not just a number. I NEVER expected to praise an airline lol I’ll definitely go out of my way to fly with Alaska on future trips. Thank you for such an awesome experience!

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

Nice crew, healthy snacks and drinks available. Flight to Seattle was short and comfortable.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

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

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

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

Information on your arrival and departure airports