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$51+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in September or August, booked 65 days in advance, depart on a Sunday or Wednesday and return on a Monday

Cheap 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 August 18, 2025.

Round-trip from

$204
(Mytrip)

One-way from

$51
(Cheapflightsfares)

Popular in

November

Cheapest in

September

Average price

$286

Good round-trip deal

$316 or less

Good one-way deal

$189 or less
From Oakland to Chicago (CHI)
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One-way flight from Oakland to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Oakland to Chicago (CHI).
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Price to beat on a one-way flight from Oakland to Chicago (CHI).
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Find 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 August 18, 2025.

This Mytrip deal was found by Cheapflights users on 8/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amOAK - ORD
2 stops9h 44mSpirit Airlines
Tue 9/162:04 pmORD - OAK
3 stops21h 57mSpirit Airlines
Deal found 8/15$204
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:30 amOAK - ORD
1 stop10h 21mSpirit Airlines
Thu 9/119:00 amORD - OAK
1 stop6h 34mSpirit Airlines
Deal found 8/17$205
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Sun 9/148:01 pmORD - OAK
1 stop29h 31mSpirit Airlines
Deal found 8/17$206
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Thu 9/119:00 amORD - OAK
1 stop6h 34mSpirit Airlines
Deal found 8/17$207
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2610:56 amOAK - ORD
2 stops9h 44mMultiple Airlines
Sun 10/51:03 pmORD - OAK
1 stop20h 46mMultiple Airlines
Deal found 8/18$208
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/510:56 amOAK - ORD
1 stop10h 19mMultiple Airlines
Sun 9/77:55 amORD - OAK
1 stop28h 06mMultiple Airlines
Deal found 8/17$209
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Mon 9/86:05 pmORD - OAK
1 stop7h 27mSpirit Airlines
Deal found 8/18$210
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Sat 9/209:00 amORD - OAK
1 stop6h 34mSpirit Airlines
Deal found 8/16$213
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/812:15 pmOAK - ORD
2 stops17h 39mMultiple Airlines
Mon 11/1010:43 pmORD - OAK
1 stop14h 27mMultiple Airlines
Deal found 8/16$214
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Sun 9/288:01 pmORD - OAK
1 stop29h 31mSpirit Airlines
Deal found 8/17$215
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Sat 9/69:00 amORD - OAK
1 stop6h 34mSpirit Airlines
Deal found 8/18$216
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 11/47:35 amOAK - MDW
1 stop7h 20mSouthwest
Sat 11/82:05 pmMDW - OAK
Nonstop4h 40mSouthwest
Deal found 8/17$237

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 August 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 - ORD

OAKORD

Oakland

Tue 9/9

6:30 am-6:14 pm

2 stops9h 44m

Chicago O'Hare Intl

Tue 9/16

2:04 pm-10:01 am

3 stops21h 57m

$204

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 9/13

2:07 pm-7:18 pm

1 stop7h 11m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 9/20

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Tue 9/23

11:15 am-11:32 pm

1 stop14h 17m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Thu 9/11

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 9/8

10:56 am-9:32 pm

2 stops8h 36m

Chicago O'Hare Intl

Tue 9/9

11:15 am-11:32 pm

1 stop14h 17m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/25

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Mon 9/29

9:00 am-1:34 pm

1 stop6h 34m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Sun 9/14

8:01 pm-11:32 pm

1 stop29h 31m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/9

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Sun 9/14

8:01 pm-11:32 pm

1 stop29h 31m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/26

10:56 am-10:40 pm

2 stops9h 44m

Chicago O'Hare Intl

Sun 10/5

1:03 pm-7:49 am

1 stop20h 46m

$208

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/5

10:56 am-11:15 pm

1 stop10h 19m

Chicago O'Hare Intl

Sun 9/7

7:55 am-10:01 am

1 stop28h 06m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 35 results
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The best insider tips for Oakland to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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

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 August 8, 2025.

The best time to book flights from Oakland, California to Chicago is 64 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, August is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $245). Flying from Oakland, California to Chicago in March is currently the most expensive (average of $321). 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 August 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 evening could potentially save you up to 36% 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 August 17, 2025.

Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Saturday 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?

What’s the top layover airport for flights from Oakland, California to Chicago?

Share of 1-stop round-trip flights from Oakland, California to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Las Vegas (LAS) – chosen by Cheapflights users on 80% of 1-stop itineraries from Oakland, California to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Oakland, California to Chicago?

Average round-trip fare for 1-stop flights from Oakland, California to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $152.

What’s the fastest layover option from Oakland, California to Chicago?

Shortest average travel time for 1-stop one-way flights from Oakland, California to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 6h 05m.

Which airport typically offers the quickest layover for flights from Oakland, California to Chicago?

Average layover duration for 1-stop one-way flights from Oakland, California to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 3h 15m.

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 August 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
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,038 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 is 1 daily outbound flight to Chicago from 4 different airlines.

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

    For as low as $237, Spirit Airlines can have you in Chicago from Oakland, California in 7h 20m. 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 $108. 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 68% 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, August is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $245). Flying from Oakland, California to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$220FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$287FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$356FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$242Average$405FlexibilityNo cancel feeOn-time63%

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