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$61+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Jan 25 — Feb 11
Sat 1/25
Sat 2/1
1 adult, Economy
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The best prices from Oakland to Chicago are usually found in April or August, booked 89 days in advance, depart on a Wednesday or Friday and return on a Wednesday

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 January 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Cheapflightsfares)

One-way from

$61
(Booking.com)

Popular in

June

Cheapest in

April

Average price

$333
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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High demand for flights, 8% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in January 2025
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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 January 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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 2/1212:40 pmOAK - ORD
1 stop7h 10mSpirit Airlines
Wed 2/191:32 pmORD - OAK
1 stop10h 40mSpirit Airlines
Deal found 1/19$131
This Southwest deal was found by Cheapflights users on 1/19. 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.
Sun 2/98:05 amOAK - ORD
1 stop11h 25mSouthwest
Tue 2/115:45 amORD - OAK
2 stops9h 55mSouthwest
Deal found 1/19$252
This Delta deal was found by Cheapflights users on 1/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/251:15 pmOAK - ORD
1 stop6h 12mDelta
Fri 2/287:18 pmORD - OAK
1 stop6h 38mDelta
Deal found 1/18$257
This Delta deal was found by Cheapflights users on 1/19. 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.
Wed 9/310:45 pmOAK - MDW
2 stops11h 45mDelta
Tue 9/161:05 pmMDW - OAK
1 stop10h 27mDelta
Deal found 1/19$262
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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 4/86:43 amOAK - ORD
1 stop20h 57mAlaska Airlines
Wed 4/165:53 pmORD - OAK
1 stop7h 50mAlaska Airlines
Deal found 1/19$286
This Southwest deal was found by Cheapflights users on 1/19. 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.
Sun 2/236:10 amOAK - MDW
Nonstop4h 05mSouthwest
Tue 2/258:30 amMDW - OAK
1 stop7h 00mSouthwest
Deal found 1/19$288
This Mytrip deal was found by Cheapflights users on 1/19. 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.
Wed 1/297:42 amOAK - ORD
2 stops20h 13mMultiple Airlines
Mon 2/311:45 amORD - OAK
3 stops13h 51mMultiple Airlines
Deal found 1/19$308
This Mytrip deal was found by Cheapflights users on 1/19. 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.
Wed 1/227:02 pmOAK - RFD
1 stop14h 52mMultiple Airlines
Sun 1/2612:44 pmRFD - OAK
1 stop12h 52mMultiple Airlines
Deal found 1/19$608

Find flights from Oakland to Chicago within your budget

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 January 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/12

12:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 2/19

1:32 pm-10:12 pm

1 stop10h 40m

$131

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 2/9

8:05 am-9:30 pm

1 stop11h 25m

Chicago O'Hare Intl

Tue 2/11

5:45 am-1:40 pm

2 stops9h 55m

$252

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/25

1:15 pm-9:27 pm

1 stop6h 12m

Chicago O'Hare Intl

Fri 2/28

7:18 pm-11:56 pm

1 stop6h 38m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 2/23

6:10 am-12:15 pm

Nonstop4h 05m

Chicago Midway

Tue 2/25

8:30 am-1:30 pm

1 stop7h 00m

$288

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 4/4

7:00 pm-9:44 am

2 stops12h 44m

Chicago O'Hare Intl

Wed 4/9

5:53 pm-11:43 pm

1 stop7h 50m

$308

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 3/3

9:46 am-5:53 am

2 stops18h 07m

Chicago O'Hare Intl

Sat 3/8

5:56 pm-11:43 pm

1 stop7h 47m

$335

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 3/13

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Tue 3/18

2:55 pm-11:59 pm

2 stops11h 04m

$358

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 2/27

5:10 am-9:50 pm

1 stop14h 40m

$61

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 3/2

6:10 am-12:15 pm

Nonstop4h 05m

$109

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/8

2:10 pm-11:40 pm

1 stop7h 30m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 17 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star

*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.

Travel insights for flights from Oakland to Chicago

Get recent, data-driven insights about flights from Oakland to Chicago including ideal travel times, pricing trends, and more.

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 January 17, 2025.

The best time to book flights from Oakland, California to Chicago is 86 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 $320). 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 January 20, 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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 15% 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 December 16, 2024.

Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Wednesday 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.

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 January 20, 2025.

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

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 January 20, 2025.
Peruse reviews from past customers who have flown with Spirit 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.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Spirit Airlines
6.3
Okay
8,113 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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.

  • 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 $131. Other airlines that can offer you cheap pricing are Southwest, from $252, and Delta, from $257. Users have found that Spirit Airlines is 57% 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 $61. Users have also found prices from $109 and $134 on Southwest and Delta, 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 $320). 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 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 January 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$292FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$416FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$467FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$400FlexibilityNo cancel feeOn-time63%
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