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$129+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in July or February, booked 20 days in advance, depart on a Wednesday or Friday 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 May 10, 2026.

This Southwest deal was found by Cheapflights users on 5/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:55 pm
OAK
-
MDW
1 stop7h 05m
Southwest
Wed 7/15:35 am
MDW
-
OAK
1 stop6h 15m
Southwest
Deal found 5/5$320
This Southwest deal was found by Cheapflights users on 5/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:55 am
OAK
-
MDW
1 stop7h 10m
Southwest
Tue 10/66:20 am
MDW
-
OAK
2 stops7h 55m
Southwest
Deal found 5/5$321
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 8/266:55 pm
OAK
-
MDW
1 stop7h 35m
Southwest
Sat 8/291:55 pm
MDW
-
OAK
Nonstop4h 25m
Southwest
Deal found 5/8$324
This Southwest deal was found by Cheapflights users on 5/8. 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.
Fri 5/291:25 pm
OAK
-
MDW
1 stop7h 15m
Southwest
Wed 6/36:10 am
MDW
-
OAK
1 stop6h 50m
Southwest
Deal found 5/8$325
This CheapOair deal was found by Cheapflights users on 5/6. 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 6/58:13 pm
OAK
-
ORD
1 stop20h 37m
Alaska Airlines
Tue 6/92:10 pm
ORD
-
OAK
1 stop11h 40m
Alaska Airlines
Deal found 5/6$325
This Southwest deal was found by Cheapflights users on 5/7. 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.
Sat 5/305:40 am
OAK
-
MDW
2 stops9h 35m
Southwest
Wed 6/37:55 am
MDW
-
OAK
1 stop6h 35m
Southwest
Deal found 5/7$326
This CheapOair deal was found by Cheapflights users on 5/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:50 pm
OAK
-
ORD
1 stop6h 46m
Alaska Airlines
Wed 7/226:20 am
ORD
-
OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/7$326
This Southwest deal was found by Cheapflights users on 5/6. 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 6/163:55 pm
OAK
-
MDW
1 stop6h 10m
Southwest
Tue 6/235:50 pm
MDW
-
OAK
2 stops7h 30m
Southwest
Deal found 5/6$327
This Southwest deal was found by Cheapflights users on 5/7. 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.
Tue 6/212:25 pm
OAK
-
ORD
2 stops8h 30m
Southwest
Wed 6/310:30 am
ORD
-
OAK
2 stops9h 45m
Southwest
Deal found 5/7$327
This Southwest deal was found by Cheapflights users on 5/6. 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 5/298:30 pm
OAK
-
MDW
1 stop6h 05m
Southwest
Mon 6/16:25 pm
MDW
-
OAK
1 stop7h 30m
Southwest
Deal found 5/6$329
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 6/12:58 pm
OAK
-
ORD
1 stop6h 57m
Alaska Airlines
Fri 6/52:10 pm
ORD
-
OAK
1 stop11h 40m
Alaska Airlines
Deal found 5/6$329
This Southwest deal was found by Cheapflights users on 5/9. 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.
Sat 5/306:00 pm
OAK
-
MDW
1 stop9h 50m
Southwest
Fri 6/58:15 pm
MDW
-
OAK
1 stop6h 00m
Southwest
Deal found 5/9$330

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(Southwest)

One-way from

$129
(Southwest)

Popular in

December

Cheapest in

July

Average price

$378

Good round-trip deal

$451 or less

Good one-way deal

$238 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. 27% potential increase in price ($168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 10, 2026.
Use the filters below to find and compare flights from Oakland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 5/29

8:30 pm-4:35 am

1 stop6h 05m

Chicago Midway

Tue 6/2

5:35 pm-10:25 pm

1 stop6h 50m

$325

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 6/6

7:50 pm-5:10 am

1 stop7h 20m

Chicago Midway

Tue 6/9

5:25 pm-10:25 pm

1 stop7h 00m

$340
Quickest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 7/25

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Mon 7/27

5:20 am-9:45 am

1 stop6h 25m

$345

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 9/14

1:29 pm-11:57 pm

1 stop8h 28m

Chicago O'Hare Intl

Thu 9/17

7:00 am-12:49 pm

1 stop7h 49m

$355

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 7/21

12:30 pm-9:48 pm

1 stop7h 18m

Chicago O'Hare Intl

Tue 7/28

7:40 pm-11:50 pm

1 stop6h 10m

$355

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 7/9

5:00 am-1:55 pm

1 stop6h 55m

Chicago Midway

Mon 7/13

5:20 am-9:45 am

1 stop6h 25m

$355

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 7/8

5:15 am-2:35 pm

2 stops7h 20m

Chicago Midway

Sun 7/12

5:25 am-11:10 am

1 stop7h 45m

$357

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 8/7

8:10 pm-1:21 pm

1 stop15h 11m

Chicago O'Hare Intl

Mon 8/10

7:59 pm-9:57 am

1 stop15h 58m

$364

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/30

3:00 pm-11:57 pm

1 stop6h 57m

Chicago O'Hare Intl

Sat 10/3

2:17 pm-9:48 pm

1 stop9h 31m

$365

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 7/3

9:05 pm-5:25 am

1 stop6h 20m

Chicago Midway

Mon 7/6

5:20 am-9:45 am

1 stop6h 25m

$373

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 47 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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?

The best time to book flights from Oakland, California to Chicago is 18 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 $93). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $274). 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 May 10, 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 57% on airfare.

Weekly flight availability from Oakland, California to Chicago

Explore weekly flight availability from Oakland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 10, 2026.

The most flights from OAK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 May 10, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, andUnited Airlines 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
7.9
Good
12,352 reviews

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Alaska Airlines
7.9
Good
12,352 reviews
Alaska Airlines
7.9
Good
12,352 reviews

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Southwest
7.9
Good
4,301 reviews
Alaska Airlines
7.9
Good
12,352 reviews

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
United Airlines
7.4
Good
9,698 reviews
Alaska Airlines
7.9
Good
12,352 reviews

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Spirit Airlines
6.3
Okay
8,634 reviews
Alaska Airlines
7.9
Good
12,352 reviews

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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 $325, Southwest can have you in Chicago from Oakland, California in 6h 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 $163. Other airlines that can offer you cheap pricing are Spirit Airlines, from $172, and Alaska Airlines, from $237. Users have found that United Airlines is 63% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Oakland, California to Chicago one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $84. Users have also found prices from $99 and $128 on Southwest and Alaska Airlines, respectively.

  • 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 $93). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $274). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$172Average$222FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$237Average$522FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$430FlexibilityNo cancel feeOn-time63%

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