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$99+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Mar 11 — Mar 181
Wed 3/11
Wed 3/18
1 adult, Economy
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Find cheap flights from Oakland to Chicago with Cheapflights

1. Tell us where you want to go

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

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 February 9, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:00 am
OAK
-
ORD
1 stop21h 39m
Alaska Airlines
Tue 4/146:00 am
ORD
-
OAK
1 stop19h 43m
Alaska Airlines
Deal found 2/5$186
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
OAK
-
ORD
1 stop9h 46m
Alaska Airlines
Wed 5/203:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 2/5$197
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/68:10 pm
OAK
-
ORD
1 stop15h 03m
Alaska Airlines
Tue 4/148:00 am
ORD
-
OAK
1 stop17h 43m
Alaska Airlines
Deal found 2/5$209
This Southwest deal was found by Cheapflights users on 2/8. 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 3/2411:55 pm
OAK
-
MDW
Nonstop4h 00m
Southwest
Sat 3/289:40 pm
MDW
-
OAK
Nonstop4h 40m
Southwest
Deal found 2/8$217
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:43 am
OAK
-
ORD
2 stops12h 16m
Alaska Airlines
Wed 4/158:00 am
ORD
-
OAK
1 stop17h 43m
Alaska Airlines
Deal found 2/5$218
This Alaska Airlines deal was found by Cheapflights users on 2/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/223:18 pm
OAK
-
ORD
1 stop25h 45m
Alaska Airlines
Thu 4/303:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/8$220
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
OAK
-
ORD
1 stop14h 41m
Alaska Airlines
Sat 5/309:00 am
ORD
-
OAK
1 stop16h 37m
Alaska Airlines
Deal found 2/5$221
This Southwest deal was found by Cheapflights users on 2/7. 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 3/138:30 pm
OAK
-
MDW
1 stop6h 05m
Southwest
Mon 3/169:30 pm
MDW
-
OAK
Nonstop4h 40m
Southwest
Deal found 2/7$227
This Alaska Airlines deal was found by Cheapflights users on 2/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Wed 5/203:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 2/7$230
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 4/1510:45 am
OAK
-
MDW
2 stops7h 10m
Southwest
Thu 4/169:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 2/9$232
This Alaska Airlines deal was found by Cheapflights users on 2/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:29 am
OAK
-
ORD
1 stop6h 17m
Alaska Airlines
Sat 5/169:00 am
ORD
-
OAK
1 stop16h 37m
Alaska Airlines
Deal found 2/7$233
This Southwest deal was found by Cheapflights users on 2/8. 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 3/106:50 am
OAK
-
MDW
1 stop7h 50m
Southwest
Tue 3/175:10 pm
MDW
-
OAK
1 stop8h 10m
Southwest
Deal found 2/8$237

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 February 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(Alaska Airlines)

One-way from

$99
(Expedia)

Popular in

December

Cheapest in

July

Average price

$328

Good round-trip deal

$361 or less

Good one-way deal

$178 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. 28% potential increase in price ($171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 9, 2026.
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

Wed 4/8

7:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Tue 4/14

8:00 am-11:43 pm

1 stop17h 43m

$186

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/13

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Tue 5/19

9:00 am-2:32 pm

1 stop7h 32m

$223

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 4/15

8:20 am-4:35 pm

1 stop6h 15m

Chicago Midway

Thu 4/16

9:50 pm-12:25 am

Nonstop4h 35m

$227

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 4/16

1:25 pm-10:40 pm

1 stop7h 15m

Chicago Midway

Sat 4/18

5:55 pm-8:30 pm

Nonstop4h 35m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/13

10:29 am-6:46 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 5/16

9:00 am-11:37 pm

1 stop16h 37m

$233

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/10

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 3/17

7:10 pm-11:46 pm

1 stop6h 36m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 5/4

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Mon 5/11

9:50 pm-12:25 am

Nonstop4h 35m

$248

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 4/10

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 4/15

8:50 pm-11:25 pm

Nonstop4h 35m

$248

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

3:18 pm-6:40 am

2 stops13h 22m

Chicago O'Hare Intl

Thu 4/30

3:52 pm-10:23 pm

1 stop8h 31m

$258

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 4/10

8:55 pm-5:00 am

1 stop6h 05m

Chicago Midway

Mon 4/13

9:50 pm-12:25 am

Nonstop4h 35m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 43 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 February 6, 2026.

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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $123). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $233). 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 February 9, 2026.

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 54% on airfare.

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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 February 9, 2026.
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
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,867 reviews
Alaska Airlines
8.0
Very good
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,176 reviews
Alaska Airlines
8.0
Very good
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,262 reviews
Alaska Airlines
8.0
Very good
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Spirit Airlines
6.3
Okay
8,433 reviews
Alaska Airlines
8.0
Very good
11,867 reviews

Crew

8.5

Entertainment

7.0

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 $227, Alaska Airlines can have you in Chicago from Oakland, California in 6h 15m. 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 74% 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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $123). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $233). 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 February 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$356FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$532FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$417FlexibilityNo cancel feeOn-time63%

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