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$67+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 Friday 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$221
(Mytrip)

One-way from

$67
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$387

Good round-trip deal

$376 or less

Good one-way deal

$243 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)
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Highest demand for flights based on searches. 15% potential increase in price ($57 potential increase over avg. RT price).
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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 March 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 March 26, 2025.

This Mytrip deal was found by Cheapflights users on 3/26. 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.
Fri 4/257:31 pmOAK - ORD
2 stops32h 33mSpirit Airlines
Mon 4/287:41 amORD - OAK
2 stops30h 22mSpirit Airlines
Deal found 3/26$221
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 4/156:43 amOAK - ORD
1 stop9h 12mAlaska Airlines
Tue 4/223:44 pmORD - OAK
1 stop10h 00mAlaska Airlines
Deal found 3/24$246
This Southwest deal was found by Cheapflights users on 3/24. 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 4/292:55 pmOAK - MDW
1 stop7h 00mSouthwest
Tue 5/61:50 pmMDW - OAK
1 stop7h 40mSouthwest
Deal found 3/24$247
This Southwest deal was found by Cheapflights users on 3/24. 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 4/155:15 amOAK - ORD
2 stops9h 30mSouthwest
Tue 4/225:45 pmORD - OAK
1 stop7h 00mSouthwest
Deal found 3/24$252
This Delta deal was found by Cheapflights users on 3/25. 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.
Thu 4/175:10 pmOAK - ORD
1 stop5h 43mDelta
Sun 4/207:25 amORD - OAK
1 stop6h 48mDelta
Deal found 3/25$257
This Delta deal was found by Cheapflights users on 3/25. 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.
Sun 4/206:00 amOAK - MDW
2 stops9h 19mDelta
Tue 4/221:16 pmMDW - OAK
2 stops12h 27mDelta
Deal found 3/25$262
This Booking.com deal was found by Cheapflights users on 3/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2910:36 amOAK - ORD
2 stops16h 49mMultiple Airlines
Sun 6/17:00 amORD - OAK
1 stop11h 34mMultiple Airlines
Deal found 3/24$265
This Hawaiian Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 9/32:33 pmOAK - ORD
1 stop7h 26mHawaiian Airlines
Tue 9/163:15 pmORD - OAK
1 stop8h 48mHawaiian Airlines
Deal found 3/25$276
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Thu 4/37:31 amOAK - RFD
1 stop11h 20mMultiple Airlines
Sun 4/69:41 pmRFD - OAK
1 stop10h 55mMultiple Airlines
Deal found 3/25$279
This Mytrip deal was found by Cheapflights users on 3/24. 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.
Sat 6/141:08 pmOAK - MDW
2 stops28h 11mMultiple Airlines
Thu 6/198:09 pmMDW - OAK
3 stops29h 30mMultiple Airlines
Deal found 3/24$496

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 March 26, 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

Fri 4/25

7:31 pm-6:04 am

2 stops32h 33m

Chicago O'Hare Intl

Mon 4/28

7:41 am-12:03 pm

2 stops30h 22m

$221

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/15

6:43 am-5:55 pm

1 stop9h 12m

Chicago O'Hare Intl

Sat 4/19

2:04 pm-7:37 pm

1 stop7h 33m

$246

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 4/29

2:55 pm-11:55 pm

1 stop7h 00m

Chicago Midway

Tue 5/6

1:50 pm-7:30 pm

1 stop7h 40m

$247

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/15

5:15 am-4:45 pm

2 stops9h 30m

Chicago O'Hare Intl

Tue 4/22

5:45 pm-10:45 pm

1 stop7h 00m

$252

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 4/17

5:10 pm-12:53 am

1 stop5h 43m

Chicago O'Hare Intl

Sun 4/20

7:25 am-12:13 pm

1 stop6h 48m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 4/20

6:00 am-5:19 pm

2 stops9h 19m

Chicago Midway

Tue 4/22

1:16 pm-11:43 pm

2 stops12h 27m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 5/29

10:36 am-5:25 am

2 stops16h 49m

Chicago O'Hare Intl

Sun 6/1

7:00 am-4:34 pm

1 stop11h 34m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/3

2:33 pm-11:59 pm

1 stop7h 26m

Chicago O'Hare Intl

Tue 9/16

3:15 pm-10:03 pm

1 stop8h 48m

$276

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Thu 4/24

7:46 am-8:46 pm

1 stop11h 00m

Chicago Greater Rockford

Sun 4/27

9:36 pm-6:49 am

1 stop11h 13m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 6/14

1:08 pm-7:19 pm

2 stops28h 11m

Chicago Midway

Thu 6/19

8:09 pm-11:39 pm

3 stops29h 30m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 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 March 21, 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 $323). 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 March 26, 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.

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 March 16, 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.

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 March 26, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Hawaiian Airlines
7.9
Good
2,331 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Sun Country Air
6.9
Okay
348 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Crew

8.6

Overall

8.1

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 $221. Other airlines that can offer you cheap pricing are Alaska Airlines, from $246, and Southwest, from $247. Users have found that Spirit Airlines is 29% 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 $67. Users have also found prices from $99 and $108 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 $323). 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
New Buffalo
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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$130Average$285FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$377FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$185Average$257FlexibilityNo cancel feeOn-time69%
DeltaCheapest$235Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$423FlexibilityNo cancel feeOn-time63%
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