CHI - OAK

$66 Find Cheap Flights from Chicago to Oakland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Oakland departing on 6/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Oakland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flights from Chicago to Oakland

 
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.

Recent round-trip flight deals from Chicago to Oakland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Oakland.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
11:50 am - 8:14 pmORD-OAK
10h 24m1 stop
Spirit Airlines Logo
9:09 pm - 10:55 amOAK-ORD
11h 46m1 stop
$136Spirit Airlines
Find Deal
Tue, Jun 3 - Mon, Jun 9
Spirit Airlines Logo
11:50 am - 10:25 pmORD-OAK
12h 35m1 stop
Spirit Airlines Logo
9:09 pm - 5:25 amOAK-ORD
6h 16m1 stop
$142Spirit Airlines
Find Deal
Wed, May 21 - Sun, May 25
Alaska Airlines Logo
8:00 am - 1:36 pmORD-OAK
7h 36m1 stop
Alaska Airlines Logo
12:48 pm - 11:59 pmOAK-ORD
9h 11m1 stop
$206Alaska Airlines
Find Deal
Wed, May 28 - Sat, May 31
Alaska Airlines Logo
6:00 am - 1:36 pmORD-OAK
9h 36m1 stop
Alaska Airlines Logo
12:48 pm - 11:59 pmOAK-ORD
9h 11m1 stop
$216Alaska Airlines
Find Deal
Tue, Jun 3 - Wed, Jun 11
 Logo
6:00 am - 1:36 pmORD-OAK
9h 36m1 stop
 Logo
9:09 pm - 10:55 amOAK-ORD
11h 46m1 stop
Thu, May 29 - Thu, Jun 5
Southwest Logo
8:35 am - 1:00 pmMDW-OAK
6h 25m1 stop
Southwest Logo
4:25 pm - 12:50 amOAK-MDW
6h 25m1 stop
$247Southwest
Find Deal
Wed, Jun 4 - Tue, Jun 10
 Logo
9:35 pm - 11:26 pmORD-OAK
27h 51m1 stop
 Logo
5:03 pm - 5:21 pmOAK-ORD
22h 18m1 stop
Fri, Jun 20 - Sun, Jun 22
Southwest Logo
6:45 pm - 11:15 pmMDW-OAK
6h 30m1 stop
Southwest Logo
6:50 am - 4:55 pmOAK-MDW
8h 05m2 stops
$252Southwest
Find Deal
Tue, Jun 3 - Wed, Jun 11
Delta Logo
7:15 pm - 11:49 pmORD-OAK
6h 34m1 stop
Delta Logo
12:30 pm - 10:09 pmOAK-ORD
7h 39m1 stop
$257Delta
Find Deal
Thu, Jun 5 - Tue, Jun 10
Delta Logo
8:40 am - 4:15 pmORD-OAK
9h 35m2 stops
Delta Logo
12:30 pm - 10:09 pmOAK-ORD
7h 39m1 stop
$262Delta
Find Deal
Wed, Jun 4 - Sat, Jun 14
Useful Info

KAYAK's insights & trends for Chicago to Oakland flights

Get data-powered insights and trends into flights from Chicago to Oakland to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Oakland flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Oakland.

Our data shows that the cheapest route for a return flight from Chicago to Oakland cost $198 and was between Chicago Midway Airport (MDW) and Oakland (OAK). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $198.

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

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

If your flying dates are flexible, you should consider flying to Oakland on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Oakland. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Chicago to Oakland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Oakland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Oakland is July, where tickets cost $241 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $442 and $380 respectively.

Good to know

Low seasonApril
High seasonSeptember
Cheapest flight$66
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Oakland

When to book flights from Chicago to Oakland

Are your dates flexible? Find out the best times to travel from Chicago to Oakland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Oakland

  • Are there lounges in O'Hare International Airport (ORD) where passengers can await their departures?

    There are various lounge facilities within the different terminals at the airport. The main lounge in Terminal 1 is the United Club by United airlines which has four lounges: near Gates C16, C18, B18, and B6. The other is the Delta Sky Club in Terminal 2, where United Club also has a place on the grid. There are also multiple other lounge facilities in Terminal 3, mainly occupied by American Airlines. Additionally, the Admiral Club lounges are located between Gates H6 and K6, Gate L1, and near Gate G8. Terminal 5 has some lounges in it.

  • Are there any hotels near Oakland International Airport (OAK)?

    The SpringHill Suites by Marriott Oakland Airport is among the most convenient hotels where you can book a room in the case of late arrival at the airport. It is located 1.7 miles away and has facilities such as an indoor spa.

  • Are there Pet Relief Areas in O'Hare International Airport (ORD)?

    There are several Pet Relief Areas in O'Hare International Airport (ORD). An area inside Terminal 1's lower level is accessible by taking the elevator to the lower level and proceeding to the Baggage Claim, exit through Door 1A, and you will have the area on your left. Terminal 2's location is accessible by taking the elevator to the lower level, exiting through Door 2E, and the site will also be on your left. Terminal 3 is located inside the Main Hall of the airport next to the Lotto booth found near Gate K1.

  • What flights are available from O’Hare International Airport (ORD) to Oakland International Airport (OAK)?

    There are both direct and connecting flights between the destinations. Spirit Airlines is the only airline that offers direct flights between the destinations. However, they also have flights with a layover at Harry Reid International Airport (LAS). Delta Airlines also makes flights with a layover at Salt Lake City International Airport (SLC).

  • What is the cheapest flight from Chicago to Oakland?

    In the last 3 days, the lowest price for a flight from Chicago to Oakland was $66 for a one-way ticket and $136 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, Alaska Airlines, and Hawaiian Airlines offer inflight Wi-Fi service on the Chicago to Oakland flight route.

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

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

  • 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 Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Oakland are Southwest and Delta. With an average price for the route of $377 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $367 and an overall rating of 8.0.

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

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

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

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

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

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

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

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

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $166 or less one-way and $287 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?

Find which airlines fly direct from Chicago to Oakland Airport, which days they fly and book direct flights.

Direct departures

Chicago to Oakland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Oakland to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Oakland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oakland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Oakland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9968 reviews
7.1Entertainment
8.5Crew
8.2Boarding
7.1Food
7.9Comfort
Airline reviews

Boarding was quick and easy as always the crew is on their game as always I always have an enjoyable flight so I’m good.

10.0 ExcellentAnonymous, Apr 2025EUG - LAX
Read more Alaska Airlines reviews

Boarding was quick and easy as always the crew is on their game as always I always have an enjoyable flight so I’m good.

Need to get on train for second flight it’s much nicer when all the gates are together for obvious reasons

Cramped, crowded aircraft. Poorly organized boarding. Tasteless crackers to eat. 40 minutes late. A standard US air travel experience.

It was my first time flying Alaska Airlines and first time flying from Santa Rosa airport. The staff was very professional and friendly. Their instructions were clear and any question was answered satisfactorily. My seat was comfortable and the in-flight beverage service very adequate for the duration of the flight. We arrived ahead of the scheduled landing time and deplaning was simple. I look forward to flying with Alaska again.

Flight attendant took my carefully folded coat and flung it across the aisle to the bin across the way. Where one of the passengers rescued it for me, because that just wasn’t right!!

the flight was delayed twice and then delayed from taking off.

Crew was very good. Problem was not Alaska Airlines’ fault, there was a horrible, squealing, screaming kid near me.

Ted. F/A in fist class did a great job! Very nice

This was my first trip in years with Alaska. I don’t think I’ll do it again. The planes are old and tired looking. The seats are small with zero legroom. The JFK terminal is one of the worst I’ve been in. On this flight the pilot had to abort the landing and circle the Bay before trying again. I think I’ll stick with the usual suspects …

Flight was over an hour late, and we got notified every 15 minutes, beginning right at boarding, that it would only be 15 more minutes until we finally left about 75 minutes late. Of course, no compensation was offered.

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

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

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

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

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

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Great. Flight departed early and arrived early. Deplaning and baggage claim ww were quick.

They separated our seats and moved us to the back of the plane. Hundreds of dollars and thousands of miles used and this was my platinum member experience.

AC barely worked on a 50 minute flight. It was very warm the whole flight. Flight was very bumpy and hard landing.

Got on the plane and then needed to deboard the plane because they didn’t have any pilots?

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

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

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

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

Unclear pricing; ended up being charged an extra $52 just to get onboard

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

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

would be great to get basic water, soda at least and stop charging for carry ons

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your crew is a representation of your Standards and Values. The crew from Seattle to LAX, was very disappointing. The crew was more interested in hanging out at the lobby area. Talking, laughing loudly and eating all the snacks. They did not do regular rounds to see if customers needed anything. This was a huge disappointment. I will no longer be flying with your airlines moving forward.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.