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OAK - CHI

$69 Find cheap flights from Oakland, California 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 6/11. 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
Fri 6/21
Fri 6/28

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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 43,423,329 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
8:04 pm - 6:00 amOAK-ORD
7h 56m1 stop
1:13 pm - 6:35 pmORD-OAK
7h 22m1 stop
$139Spirit Airlines
Find Deal
Thu, Aug 22 - Fri, Aug 23
5:30 am - 9:55 pmOAK-ORD
14h 25m1 stop
10:01 pm - 11:12 amORD-OAK
15h 11m1 stop
$152Spirit Airlines
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Tue, Jun 4 - Tue, Jun 11
11:59 pm - 7:06 pmOAK-ORD
17h 07m1 stop
10:01 pm - 11:12 amORD-OAK
15h 11m1 stop
Sun, Jun 9 - Tue, Jun 11
11:59 pm - 7:06 pmOAK-ORD
17h 07m1 stop
10:01 pm - 12:25 pmORD-OAK
16h 24m2 stops
Sun, Jun 9 - Tue, Jun 11
10:55 pm - 8:05 amOAK-ORD
7h 10m1 stop
7:20 am - 12:02 pmORD-OAK
6h 42m1 stop
$236Delta
Find Deal
Sat, Jun 29 - Sat, Jul 6
10:45 pm - 9:17 amOAK-MDW
8h 32m1 stop
2:05 pm - 9:35 pmMDW-OAK
9h 30m1 stop
$288Delta
Find Deal
Fri, Sep 20 - Sat, Sep 28
6:15 pm - 12:15 amOAK-MDW
4h 00mnonstop
10:40 pm - 1:10 amMDW-OAK
4h 30mnonstop
$384Southwest
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Wed, Jun 5 - Fri, Jun 7
5:35 pm - 1:15 amOAK-MDW
5h 40m1 stop
10:40 pm - 1:10 amMDW-OAK
4h 30mnonstop
$389Southwest
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Wed, Jun 5 - Fri, Jun 7
11:59 pm - 8:47 amOAK-MDW
30h 48m1 stop
8:45 pm - 8:30 pmMDW-OAK
25h 45m1 stop
$600Frontier
Find Deal
Thu, Nov 14 - Sun, Nov 17
6:39 pm - 8:47 amOAK-MDW
12h 08m1 stop
4:00 pm - 3:59 pmMDW-OAK
49h 59m2 stops
$687Frontier
Find Deal
Thu, Nov 14 - Sun, Nov 17

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 Wednesday and avoid Tuesdays if you are looking for the best rates. For your return to Oakland, you’ll find the best rates on Wednesdays 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 October, where tickets cost $274 on average. On the other hand, the most expensive months are June and March, where the average cost of tickets is $385 and $378 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 46 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, Sun Country Air offered the best one-way deal for that route, at $76. KAYAK users also found Oakland to Chicago round-trip flights on Spirit Airlines from $139 and on Delta from $236.

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

Each day, there are between 3 and 5 nonstop flights that take off from Oakland, California and land in Chicago, with an average flight time of 4h 04m. 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 29 flights. The most frequent day of departure is Friday, when 17% 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 4h 00m. 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 11:10 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 6:55 pm and lands at 12:55 am.

Good to know

Low season

February

High season

June
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 47% increase in price.

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 $69 for a one-way ticket and $139 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 $324 and an overall rating of 8.0, 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

 
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 9171 reviews
7.3Entertainment
8.6Crew
8.2Boarding
7.9Comfort
7.3Food
Airline reviews

Sat on tarmac for 30 minutes despite staring at three empty gates, one of which we eventually pulled into

2.0 MediocreRon, May 2024LAX - SFO
Read more about Alaska Airlines reviews

Sat on tarmac for 30 minutes despite staring at three empty gates, one of which we eventually pulled into

It was ok. Alaska was adequate. Efficient and what I paid for it was fair. The boarding area at the gate was a joke. By the time they get past the C boarding group people all line up impatiently and then it’s chaos. We were boarding early then we sat on the tarmac for 30 minutes. I would of rather sat in the airport.

The flight was mostly smooth and quiet. No seatback screens.

Everything was great. Flight was on time with no issues. It was a short connecting flight so ww didn't have food offered. The gate we got off at was very close to our connecting flight gate so that was very easy.

Great flight. No problems. Everett Airport was so easy to get into and out of. Great alternative to SeaTac. Alaska was excellent!

It was warm on the plane. Perhaps the people who were coughing quite often should be encouraged to wear a mask?! It was a long 4 hours.

Pilot warned us it was going to be bumpy, which I usually like when it is, but it wasn't, so I spent most of the flight unnecessarily wondering when it was going to get rough. Just can't win sometimes. Ha!

Flight was changed twice. Original flight was scheduled at 5:30pm. Weeks before flight, flight was changed to 7:00pm. On the date of flight, flight was delayed and departed at 9:00pm. This caused many problems and significantly affected our schedule at our destination.

I enjoyed the leg room at my seat, but I was in an exit row.

Flight itself was great! Snacks are never really good; in this case, the "butter braids" and Biscotti cookie were both hard. The attendants' were good. We felt we found a good deal on the cost. The check-in process was very smooth: Alaskan Airlines always does a good job. Boarding was pretty timely, too. We fly Alaskan whenever possible and will continue to do so.

There was a loud squeaky sound the whole time we were flying.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

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 was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

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 crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

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.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

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!!

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.
6/11Tue
1 stop
22h 46mOAK-RFD
$69
6/9Sun
1 stopSun Country Air
17h 07mOAK-ORD
$76
6/11Tue
1 stopSpirit Airlines
10h 57mOAK-ORD
$79
5/29Wed
1 stopSpirit Airlines
9h 26mOAK-ORD
$80
6/29Sat
1 stopDelta
7h 10mOAK-ORD
$118
7/20Sat
2 stopsDelta
13h 38mOAK-MDW
$123
7/24Wed
2 stopsAlaska Airlines
11h 30mOAK-ORD
$168
10/23Wed
2 stopsAlaska Airlines
21h 30mOAK-ORD
$178
5/29Wed
1 stopFrontier
13h 08mOAK-MDW
$394
5/29Wed
2 stopsFrontier
24h 48mOAK-MDW
$490

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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.
5/26Sun
multi-stop
17h 04mOAK-ORD
5/31Fri
multi-stop
6h 53mORD-OAK
$281
5/26Sun
multi-stopSpirit Airlines
8h 14mOAK-ORD
6/4Tue
multi-stopSpirit Airlines
13h 06mORD-OAK
$316
5/26Sun
multi-stopSpirit Airlines
14h 25mOAK-ORD
5/31Fri
multi-stopSpirit Airlines
6h 53mORD-OAK
$327
5/26Sun
multi-stop
17h 04mOAK-ORD
5/31Fri
multi-stop
16h 42mORD-OAK
$332
5/25Sat
multi-stopDelta
6h 38mOAK-ORD
5/29Wed
multi-stopDelta
6h 21mORD-OAK
$413
5/25Sat
multi-stopDelta
8h 59mOAK-ORD
5/29Wed
multi-stopDelta
6h 21mORD-OAK
$602
5/24Fri
multi-stopAlaska Airlines
20h 40mOAK-ORD
5/29Wed
multi-stopAlaska Airlines
10h 46mORD-OAK
$713
5/24Fri
multi-stopAlaska Airlines
20h 40mOAK-ORD
5/29Wed
multi-stopAlaska Airlines
21h 06mORD-OAK
$794
5/25Sat
multi-stopVolaris
13h 08mOAK-MDW
5/28Tue
multi-stopVolaris
26h 45mMDW-OAK
$951
5/25Sat
multi-stopVolaris
13h 08mOAK-MDW
5/28Tue
multi-stopVolaris
25h 41mMDW-OAK
$1,223

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Oakland - Chicago Flights

Departure:

Oakland (undefined)United States

Return flight deals:

Chicago - Oakland

Cabin classes:

Compare transportation modes for Oakland to Chicago

Average priceAverage duration
Flights4h 00m
Trains$4570h 00m