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$80+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
abr. 20 — abr. 271
dom. 4/20
dom. 4/27
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in April or August, booked 8 days in advance, depart on a Sunday or Wednesday and return on a Thursday

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 abril 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$80
(Cheapflightsfares)

Popular in

November

Cheapest in

April

Average price

$96

Good round-trip deal

$388 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Oakland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Oakland-Chicago (CHI) flights.
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From Oakland to Chicago (CHI)
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One-way flight from Oakland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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).
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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 abril 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
sáb. 5/109:09 pmOAK - ORD
1 stop6h 16mSpirit Airlines
mié. 5/2111:50 amORD - OAK
1 stop10h 24mSpirit Airlines
Deal found 4/14$232
This Southwest deal was found by Cheapflights users on 4/15. 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.
sáb. 5/106:05 amOAK - MDW
Nonstop4h 10mSouthwest
vie. 5/167:05 pmMDW - OAK
1 stop6h 15mSouthwest
Deal found 4/15$237
This Mytrip deal was found by Cheapflights users on 4/14. 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.
jue. 5/85:45 amOAK - RFD
1 stop13h 01mMultiple Airlines
dom. 5/119:36 pmRFD - OAK
1 stop26h 49mMultiple Airlines
Deal found 4/14$240
This Alaska Airlines deal was found by Cheapflights users on 4/14. 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.
mié. 5/288:00 amOAK - ORD
1 stop13h 56mAlaska Airlines
sáb. 5/317:00 amORD - OAK
1 stop14h 14mAlaska Airlines
Deal found 4/14$242
This Delta deal was found by Cheapflights users on 4/14. 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.
vie. 5/3012:39 pmOAK - ORD
1 stop7h 01mDelta
dom. 6/17:15 pmORD - OAK
1 stop6h 34mDelta
Deal found 4/14$257
This Delta deal was found by Cheapflights users on 4/13. 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.
mié. 5/76:00 amOAK - MDW
2 stops9h 45mDelta
sáb. 5/109:20 amMDW - OAK
2 stops8h 55mDelta
Deal found 4/13$267
This Southwest deal was found by Cheapflights users on 4/14. 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.
sáb. 7/265:10 amOAK - ORD
1 stop6h 50mSouthwest
sáb. 8/96:15 amORD - OAK
2 stops8h 00mSouthwest
Deal found 4/14$317
This Mytrip deal was found by Cheapflights users on 4/13. 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.
mié. 4/236:29 pmOAK - ORD
3 stops17h 46mMultiple Airlines
dom. 4/277:12 pmORD - OAK
1 stop26h 20mMultiple Airlines
Deal found 4/13$321
This Hawaiian Airlines deal was found by Cheapflights users on 4/13. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/137:00 amOAK - ORD
1 stop9h 01mHawaiian Airlines
mar. 5/206:00 amORD - OAK
1 stop9h 36mHawaiian Airlines
Deal found 4/13$334

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 abril 15, 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

sáb. 5/10

9:09 pm-5:25 am

1 stop6h 16m

Chicago O'Hare Intl

mié. 5/21

11:50 am-8:14 pm

1 stop10h 24m

$232

OaklandChicago

OAK - MDW

OAKMDW

Oakland

sáb. 5/10

6:05 am-12:15 pm

Nonstop4h 10m

Chicago Midway

vie. 5/16

7:05 pm-11:20 pm

1 stop6h 15m

$237

OaklandChicago

OAK - RFD

OAKRFD

Oakland

jue. 5/8

5:45 am-8:46 pm

1 stop13h 01m

Chicago Greater Rockford

dom. 5/11

9:36 pm-10:25 pm

1 stop26h 49m

$240

OaklandChicago

OAK - ORD

OAKORD

Oakland

mié. 5/28

8:00 am-11:56 pm

1 stop13h 56m

Chicago O'Hare Intl

sáb. 5/31

7:00 am-7:14 pm

1 stop14h 14m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

vie. 5/30

12:39 pm-9:40 pm

1 stop7h 01m

Chicago O'Hare Intl

dom. 6/1

7:15 pm-11:49 pm

1 stop6h 34m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mié. 5/7

6:00 am-5:45 pm

2 stops9h 45m

Chicago Midway

sáb. 5/10

9:20 am-4:15 pm

2 stops8h 55m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 7/1

9:29 pm-5:23 am

1 stop5h 54m

Chicago O'Hare Intl

dom. 7/6

6:45 am-10:51 pm

1 stop18h 06m

$285

OaklandChicago

OAK - ORD

OAKORD

Oakland

sáb. 7/26

2:50 pm-11:05 pm

1 stop6h 15m

Chicago O'Hare Intl

sáb. 8/2

12:40 pm-9:30 pm

2 stops10h 50m

$317

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 5/13

7:00 am-6:01 pm

1 stop9h 01m

Chicago O'Hare Intl

mar. 5/20

6:00 am-1:36 pm

1 stop9h 36m

$334

OaklandChicago

OAK - ORD

OAKORD

Oakland

mié. 6/4

9:09 pm-5:25 am

1 stop6h 16m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 20 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 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 April 11, 2025.

The best time to book flights from Oakland, California to Chicago is 8 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 abril 15, 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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 abril 15, 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 compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,871 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,918 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,375 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Sun Country Air
6.9
Okay
349 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 5 different airlines.

  • 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 $232. Other airlines that can offer you cheap pricing are Southwest, from $237, and Alaska Airlines, from $242. Users have found that Spirit Airlines is 25% 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 $80. Users have also found prices from $90 and $114 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, 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 Oakland?

Book flights to Oakland if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 5 airlines flying from Oakland to Chicago

Discover the top 5 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 abril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$123Average$286FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$356FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$185Average$257FlexibilityNo cancel feeOn-time69%
DeltaCheapest$235Average$325FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$425FlexibilityNo cancel feeOn-time63%

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