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OAK - CHI

Find cheap flights from Oakland to Chicago from $79

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 4/24. 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
0 bags
Sat 4/27
Sat 5/4

Search 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Chicago.
In the last 7 days travelers have searched 47,584,047 times on KAYAK, and here is why:

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Cheap flight deals from Oakland to Chicago

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 and deals for you by selecting your travel dates.
Choose your dates
7:08 pm - 6:29 amOAK-ORD
9h 21m1 stop
10:52 pm - 11:10 amORD-OAK
14h 18m1 stop
$161Spirit Airlines
Find Deal
Wed, Apr 17 - Tue, Jun 4
8:08 pm - 6:29 amOAK-ORD
8h 21m1 stop
9:27 am - 6:29 pmORD-OAK
11h 02m1 stop
$164Spirit Airlines
Find Deal
Mon, Apr 22 - Tue, Apr 23
5:05 am - 4:59 pmOAK-ORD
9h 54m1 stop
9:27 am - 7:31 pmORD-OAK
12h 04m1 stop
$166Spirit Airlines
Find Deal
Wed, Apr 17 - Tue, Apr 23
7:08 pm - 5:09 pmOAK-ORD
20h 01m1 stop
7:23 am - 10:22 amORD-OAK
28h 59m2 stops
$172Spirit Airlines
Find Deal
Wed, Apr 17 - Mon, Apr 22
10:00 am - 8:13 amOAK-ORD
20h 13m2 stops
1:13 pm - 12:45 amORD-OAK
13h 32m1 stop
$173Spirit Airlines
Find Deal
Wed, May 8 - Mon, May 13
5:05 am - 8:16 pmOAK-MDW
37h 11m2 stops
9:10 pm - 11:10 amMDW-OAK
16h 00m1 stop
Wed, Apr 17 - Tue, Jun 4
7:08 pm - 11:36 amOAK-MDW
14h 28m1 stop
9:10 pm - 6:35 pmMDW-OAK
23h 25m1 stop
Wed, Apr 17 - Tue, Jun 4
7:00 am - 9:32 pmOAK-MDW
12h 32m2 stops
6:00 am - 5:11 pmMDW-OAK
13h 11m2 stops
$268Delta
Find Deal
Wed, Apr 24 - Mon, Apr 29
4:50 pm - 12:59 amOAK-ORD
6h 09m1 stop
7:40 am - 12:33 pmORD-OAK
6h 53m1 stop
$278Delta
Find Deal
Fri, Apr 26 - Sun, Apr 28
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
8:50 pm - 8:26 pmMDW-OAK
25h 36m2 stops
$976Volaris
Find Deal
Sat, Apr 6 - Wed, Apr 10

Flights from Oakland to Chicago - Travel Insights & Trends

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.

What is the cheapest Oakland, California to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Oakland, California to Chicago.
Our data shows that the cheapest route for a one-way flight from Oakland, California to Chicago cost $212 and was between Oakland, California and Chicago Midway Airport. On average, the best prices are found if you fly this route.

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

The average price of all flights from Oakland, California to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Oakland to Chicago, you should consider leaving on a Thursday and avoid Fridays if you are looking for the best rates. For your return to Oakland, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Oakland, California 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, California to Chicago is September, where tickets cost $278 on average. On the other hand, the most expensive months are June and May, where the average cost of tickets is $422 and $385 respectively.

How far in advance should I book a flight from Oakland, California to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Oakland, California to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Oakland, California to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 76 days before departure.

Which airlines provide the cheapest flights from Oakland to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Spirit Airlines offered the best one-way deal for that route, at $79. KAYAK users also found Oakland to Chicago round-trip flights on Spirit Airlines from $161 and on Delta from $268.

How many flights are there between Oakland, California and Chicago per day?

Each day, there are between 2 and 4 nonstop flights that take off from Oakland, California and land in Chicago, with an average flight time of 4h 07m. The most common departure time is 5:00 am and most flights take off at night, while the most flights land at Chicago Midway Airport. Each week, there are 21 flights. The most frequent day of departure is Thursday, when 19% of all weekly flights depart. The fewest flights depart on a Sunday.

Which cabin class options are there for flights between Oakland, California and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Oakland to Chicago take?

Nonstop flights from Oakland generally make it to Chicago in 5h 44m. The flying distance between the two cities is 1,845 miles.

What’s the earliest departure time from Oakland to Chicago?

Early birds can take the earliest flight from Oakland, California at 5:05 am and will be landing in Chicago at 11:15 am.

What’s the latest departure time from Oakland to Chicago?

If you prefer to fly at night, the latest flight from Oakland, California to Chicago jets off at 7:30 pm and lands at 1:35 am.

Good to know

Low season

March

High season

November

Cheapest flight

$79
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly with an average 10% increase in price.
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, California to Chicago?

    In the last 3 days, the lowest price for a flight from Oakland, California to Chicago was $79 for a one-way ticket and $161 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 aircraft models fly most regularly from Oakland to Chicago?

    We unfortunately don’t have that data for this specific 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, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Oakland to Chicago are Alaska Airlines and Delta. With an average price for the route of $328 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $368 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.

See more FAQs

Top tips for finding a cheap flight from Oakland to Chicago

  • 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.
See more tips

Prefer to fly non-stop from Oakland to Chicago?

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

Nonstop 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

Nonstop 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
See more direct flights

Top 5 airlines serving from Oakland to Chicago

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 KAYAK reviews.
8.1
Alaska AirlinesOverall score based on 9126 reviews
79comfort
86crew
82boarding
74entertainment
73food
81overall
Airline reviews

only refreshments and biscuits available but it was a short flight from LAX to LAS thus it was fine.

Read more about Alaska Airlines

only refreshments and biscuits available but it was a short flight from LAX to LAS thus it was fine.

Temperature was very cold. seat was uncomfortable bc headrest did not work properly - the earflaps would not move.

High travel time and the flight was full but the staff handled it all well.

Shorten up the country? All joking aside, it was fine. Thank you very much.

When I purchased the tickets I purchased insurance as well but for some reason it didn't go through, then this past Monday I broke my leg and was unable to make my trip, I'll never book through Kayak again.

Alaska airlines is the best. Best customer service, crew, and value for money.

Alaska airlines was good! Friendly staff, good communication and respectful. The alaska airlines help in everyway they can

The reduced size overhead compartments were a surprise. They keep getting smaller and smaller while amenities keep getting fewer.

I arrived at 7:15 for an 8:30am flight. The winds in Burbank were keeping all flights down for the morning. What ensued next was absolute chaos, poor communication and chaos. I had booked a flight last minute because my boyfriends father was dying and o needed to be there immediately. There was absolutely no consideration for communication about what was happening with our flight after there was discovered to be a mechanical error. There was no mention that vouchers had been sent by email For food and I ended up wasting money on my lunch that was horrible. I literally bought the food when I had been emailed about a voucher. . I sat there now at 1:45 and tried to get some answers because the time was ticking. Your lady was so helpful and rushed me to get a flight out of United. I showed up to sfo 6+ hours late and was able to say goodbye to his father. But it was just a horribly communicated day. Please do better

I have taken 4 Alaska flights in the past 3 weeks and every single flight was delayed. They give you a $12 voucher for airport food, sometimes too late, after you’ve already eaten. That might get you a bagel. Reservations, rentals, etc have to be cancelled with no repercussions. Will be avoiding Alaska if possible.

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

I guess they don’t serve drinks on planes anymore

The flight was overbooked and the staff at the gate started calling for volunteers to drop out and offering incentives. That delayed the flight

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

The staff was phenomenal. I can’t think of anything that could be better. Will be flying with UA again

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Its so random that they only allow 40 pounds on checked bags when all airlines take 55. They then charge you for each 10 extra pounds, so my checked suitcase was $130 and the flight $30 ... its like whattt, im for sure not traveling with Spirit again

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

We waited an hour to get off of the plane

My luggage was drag on ground brand new when I got was dusty damage

Quick flight, awful security delay led to almost not boarding the flight.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

My first time to fly Frontier and loved it! Boarding was super easy as we only had personal items. Crew was helpful and funny and the plane was clean. Pilot was also great at landing the plane smoothly.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

late late late late no accountability no refund no adjustment no reasonable solution

This isna terribly run airlines. If you're one minute late, they will deny your ticket. Don't waste your time or money

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

Flight was delayed for more than 3 hours, crew at ONT airport was rude, and when we got to DFW the airplane had an issue landing, we had to be taxied to the terminal, and the luggage was hold until the next day.

Several delays in a row totaling two hours with no information announcements and no explanations given. Rude and unapologetic onboard flight attendant addressing those of us in overpriced emergency exits as if we were idiots. It had been a while since I felt treated like cattle. I will do my best to avoid Frontier as much as possible in the future.

Well the first and worst thing is that you have to pay for a carry on bag. Which they tell you if you don’t read it when you book your flight. You can do it through their website at the ticket area. The staff in Sacramento were RUDE and wouldn’t answer any questions. I will NEVER book with Frontier again. Save the headache and book with Southwest so you don’t have to pay to carry your own bag on the plane. It cost me 41 and 37. On top of my fare. Which by the way went up as soon as I booked it. First it said 38 and then wouldn’t you know it, once I was ready to book, it went up to 78.

Book cheap flights from Oakland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Oakland to Chicago found on KAYAK in the last 72 hours.
4/24Wed
1 stopSpirit Airlines
8h 21mOAK-ORD
$79
4/29Mon
1 stop
13h 28mOAK-MDW
$80
4/17Wed
1 stopAlaska Airlines
7h 49mOAK-ORD
$119
6/1Sat
2 stopsDelta
9h 05mOAK-MDW
$124
4/27Sat
2 stopsDelta
12h 09mOAK-ORD
$124
6/16Sun
1 stopSun Country Air
17h 07mOAK-ORD
$130
6/13Thu
1 stopSun Country Air
9h 34mOAK-ORD
$140
6/8Sat
1 stopAlaska Airlines
12h 15mOAK-ORD
$162
6/16Sun
1 stopVolaris
19h 32mOAK-MDW
$379
6/22Sat
1 stopVolaris
13h 08mOAK-MDW
$387

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Last minute flights from Oakland to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Oakland to Chicago that are departing in the next 10 days.
4/1Mon
multi-stopSpirit Airlines
23h 40mOAK-ORD
4/10Wed
multi-stopSpirit Airlines
15h 39mORD-OAK
$492
4/1Mon
multi-stopSpirit Airlines
23h 40mOAK-ORD
4/10Wed
multi-stopSpirit Airlines
10h 49mORD-OAK
$514
3/30Sat
multi-stopSpirit Airlines
10h 07mOAK-ORD
5/4Sat
multi-stopSpirit Airlines
7h 03mORD-OAK
$566
4/1Mon
multi-stop
10h 38mOAK-ORD
4/3Wed
multi-stop
34h 56mORD-OAK
$633
4/1Mon
multi-stop
10h 38mOAK-ORD
4/3Wed
multi-stop
18h 19mORD-OAK
$635
4/1Mon
multi-stopDelta
6h 20mOAK-ORD
4/7Sun
multi-stopDelta
6h 55mORD-OAK
$963
4/1Mon
multi-stopVolaris
13h 08mOAK-MDW
4/10Wed
multi-stopVolaris
25h 36mMDW-OAK
$1,179
3/30Sat
multi-stopDelta
8h 26mOAK-MDW
4/2Tue
multi-stopDelta
10h 05mMDW-OAK
$1,182
3/29Fri
multi-stopAlaska Airlines
13h 17mOAK-ORD
3/31Sun
multi-stopAlaska Airlines
8h 11mORD-OAK
$1,210
3/29Fri
multi-stopVolaris
15h 34mOAK-ORD
4/6Sat
multi-stopVolaris
16h 14mORD-OAK
$1,560

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Oakland - Chicago Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Chicago - Oakland

Cabin classes:

Compare transportation modes for Oakland to Chicago

Average priceAverage duration
Flights6h 09m
Trains$3290h 00m