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$109+ Cheap flights from Oakland, CA (OAK) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Find cheap flights from Oakland to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in February or July, booked 23 days in advance, depart on a Sunday or Wednesday and return on a Monday

Cheap flight deals from Oakland to Chicago

Cheapest flights from Oakland to Chicago
Explore the most affordable flight options available from Oakland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:05 pmOAK - ORD
1 stop6h 30mSouthwest
Thu 12/257:15 amORD - OAK
1 stop7h 45mSouthwest
Deal found 12/15$583
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:25 amOAK - MDW
Nonstop4h 05mSouthwest
Fri 1/29:50 amMDW - OAK
1 stop6h 55mSouthwest
Deal found 12/15$602
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:40 amOAK - ORD
1 stop6h 25mSouthwest
Fri 1/23:45 pmORD - OAK
2 stops9h 20mSouthwest
Deal found 12/15$617
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:25 amOAK - MDW
Nonstop4h 05mSouthwest
Wed 12/311:55 pmMDW - OAK
1 stop7h 25mSouthwest
Deal found 12/17$633
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:10 amOAK - MDW
Nonstop4h 05mSouthwest
Thu 1/15:00 amMDW - OAK
2 stops8h 40mSouthwest
Deal found 12/16$638
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:50 pmOAK - ORD
2 stops13h 49mDelta
Tue 12/237:25 amORD - OAK
1 stop6h 29mDelta
Deal found 12/16$639
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:15 amOAK - ORD
1 stop7h 30mSouthwest
Wed 12/314:25 pmORD - OAK
1 stop7h 20mSouthwest
Deal found 12/17$643
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:25 amOAK - MDW
1 stop6h 35mSouthwest
Sat 12/276:05 pmMDW - OAK
1 stop7h 20mSouthwest
Deal found 12/15$653
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:30 amOAK - ORD
2 stops12h 05mSouthwest
Sat 1/32:15 pmORD - OAK
2 stops10h 45mSouthwest
Deal found 12/15$653
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:10 amOAK - MDW
Nonstop4h 05mSouthwest
Tue 12/306:05 amMDW - OAK
1 stop7h 25mSouthwest
Deal found 12/16$667
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2712:40 pmOAK - ORD
2 stops7h 55mSouthwest
Thu 1/12:15 pmORD - OAK
2 stops8h 55mSouthwest
Deal found 12/16$670

Find flight deals from Oakland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Southwest)

One-way from

$109
(Southwest)

Popular in

December

Cheapest in

February

Average price

$624

Good round-trip deal

$386 or less

Good one-way deal

$179 or less
Provider with most accurate pricing for Oakland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Chicago (CHI) flights.
Search Deals
From Oakland to Chicago (CHI)
Search Deals
One-way flight from Oakland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($101 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Oakland to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oakland to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Oakland to Chicago that are best for you.

Fly from

Oakland

Fly to

Chicago

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/20

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Sat 1/24

7:40 pm-10:35 pm

Nonstop4h 55m

$236

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/14

6:40 am-12:45 pm

Nonstop4h 05m

Chicago Midway

Tue 2/17

7:55 am-12:35 pm

1 stop6h 40m

$239

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 1/10

5:55 am-12:00 pm

Nonstop4h 05m

Chicago Midway

Sat 1/17

8:35 am-2:25 pm

1 stop7h 50m

$246

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/3

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Wed 2/11

5:35 pm-10:15 pm

1 stop6h 40m

$251

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/13

11:43 am-11:50 pm

1 stop10h 07m

Chicago O'Hare Intl

Tue 1/20

2:06 pm-9:46 am

1 stop21h 40m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/20

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Fri 1/23

2:10 pm-9:45 pm

1 stop9h 35m

$258

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/20

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Fri 1/23

8:00 am-8:40 pm

1 stop14h 40m

$259

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/28

5:55 am-1:38 pm

1 stop5h 43m

Chicago O'Hare Intl

Tue 2/3

6:40 pm-11:53 pm

1 stop7h 13m

$261

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/20

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Sat 1/24

8:00 am-9:46 am

2 stops27h 46m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 2/14

5:31 pm-2:05 pm

1 stop18h 34m

Chicago O'Hare Intl

Wed 2/18

3:54 pm-9:24 am

2 stops19h 30m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 39 results
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Compare providers for flights from Oakland to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oakland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Oakland to Chicago. Price data was last updated on December 12, 2025.

The best time to book flights from Oakland, California to Chicago is 23 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Oakland, California to Chicago?

Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $107). Flying from Oakland, California to Chicago in November is currently the most expensive (average of $210). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAK to CHI?

Find hourly flight availability from Oakland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

One of the essential ways to save on airfare from Oakland, California to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Oakland to Chicago. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Oakland, California to Chicago?

The best insider tips for Oakland to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Oakland to Chicago trip
Airports
OAK

For early flights, BART offers a cost-efficient and fast connection from Oakland to San Francisco, avoiding potential bridge traffic delays.

Read more about OAKBy Bill Fink
MDW

The Orange Line train from MDW to downtown Chicago takes less than 30 minutes, offering a convenient and affordable option.

Read more about MDWBy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Bill Fink

Bill Fink

Expert on OAK

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oakland to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,475 reviews
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,249 reviews
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,006 reviews
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,091 reviews
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Spirit Airlines
6.3
Okay
8,191 reviews
Alaska Airlines
8.0
Very good
11,475 reviews

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Chicago?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago from Oakland. Booking flights from Oakland (OAK) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 4 different airlines.

  • How long is the flight from Oakland, California to Chicago?

    For as low as $236, Southwest can have you in Chicago from Oakland, California in 4h 05m. Airlines will cover a distance of 1839 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Oakland, California to Chicago round-trip?

    Cheapflights users have booked flights from Oakland, California to Chicago round-trip from $100. Other airlines that can offer you cheap pricing are United Airlines, from $163, and Alaska Airlines, from $189. Users have found that Spirit Airlines is 75% cheaper than the other options available to this destination.

  • What are the most popular routes from Oakland, California to Chicago?

    The most popular flight routes from Oakland, California to Chicago are Oakland - Chicago O'Hare Intl, Oakland - Chicago Midway and Oakland - Chicago Greater Rockford.

  • Can I find deals for flights from Oakland to Chicago that include hotel bookings?

    Yes. In addition to deals on Oakland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Chicago.

  • Can I find deals for business class flights from Oakland to Chicago?

    Yes. Cheapflights offers flight deals from Oakland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $107). Flying from Oakland, California to Chicago in November is currently the most expensive (average of $210). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Oakland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oakland to Chicago

Discover the top 4 airlines that operate flights from Oakland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$329FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$527FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$419FlexibilityNo cancel feeOn-time63%

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