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$67+ Cheap flights from Oakland (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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

April

Round-trip from

$100
(Cheapflightsfares)

One-way from

$67
(Cheapflightsfares)
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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High demand for flights, 34% potential price rise
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Best time to find cheap flights, 66% potential price drop
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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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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 October 31, 2024.

This FareScan deal was found by Cheapflights users on 10/30. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/115:27 pmOAK - ORD
2 stops23h 22mSpirit Airlines
Wed 11/1310:13 pmORD - OAK
1 stop13h 13mSpirit Airlines
Deal found 10/30$223
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 12/51:10 pmOAK - MDW
1 stop7h 30mSouthwest
Tue 12/105:10 pmMDW - OAK
Nonstop4h 45mSouthwest
Deal found 10/29$247
This eDestinos deal was found by Cheapflights users on 10/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/75:30 amOAK - ORD
1 stop16h 42mMultiple Airlines
Fri 11/85:33 pmORD - OAK
1 stop17h 53mMultiple Airlines
Deal found 10/30$263
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/125:30 amOAK - MDW
2 stops27h 34mMultiple Airlines
Fri 11/1510:49 pmMDW - OAK
1 stop17h 34mMultiple Airlines
Deal found 10/30$280
This Delta deal was found by Cheapflights users on 10/30. 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 12/1212:55 pmOAK - ORD
1 stop7h 08mDelta
Wed 12/187:10 pmORD - OAK
1 stop7h 05mDelta
Deal found 10/30$317
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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.
Fri 12/134:00 pmOAK - ORD
1 stop29h 47mAlaska Airlines
Sun 12/158:00 amORD - OAK
1 stop9h 00mAlaska Airlines
Deal found 10/31$329
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 12/305:10 amOAK - ORD
2 stops9h 35mSouthwest
Sun 1/54:20 pmORD - OAK
1 stop10h 10mSouthwest
Deal found 10/30$356
This Delta deal was found by Cheapflights users on 10/30. 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 12/56:00 amOAK - MDW
2 stops10h 32mDelta
Tue 12/101:30 pmMDW - OAK
2 stops12h 44mDelta
Deal found 10/30$377
This FlightHub deal was found by Cheapflights users on 10/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/225:59 pmOAK - MDW
1 stop12h 46mFrontier
Tue 11/267:50 pmMDW - OAK
1 stop27h 25mFrontier
Deal found 10/29$631
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Tue 11/55:59 pmOAK - MDW
1 stop12h 46mVolaris
Fri 11/810:41 pmMDW - OAK
1 stop18h 48mVolaris
Deal found 10/30$765
This Mytrip deal was found by Cheapflights users on 10/29. 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 12/211:28 pmOAK - RFD
2 stops20h 22mMultiple Airlines
Sat 12/2811:47 amRFD - OAK
2 stops23h 42mMultiple Airlines
Deal found 10/29$1,002

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 11/20

5:27 pm-4:45 am

1 stop9h 18m

$67

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 11/7

5:30 am-12:12 am

1 stop16h 42m

$91

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 1/25

7:40 am-1:45 pm

Nonstop4h 05m

$109

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 2/7

2:36 pm-11:59 pm

1 stop7h 23m

$121

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 12/7

5:15 pm-9:50 am

2 stops14h 35m

$133

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/14

1:10 pm-11:05 pm

1 stop7h 55m

$118

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 11/8

5:30 am-9:54 pm

1 stop14h 24m

$157

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 1/19

5:55 am-1:49 pm

1 stop5h 54m

$159

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/21

3:55 pm-9:26 pm

3 stops27h 31m

$335

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 12/1

11:05 pm-9:02 pm

2 stops19h 57m

$548

Flights are sorted by cheapest first

Deals found on 10/31

Showing 1-10 of 21 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 October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
PricelinePrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
Booking.comPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 starCancellation PolicyAirline Policy
CheapOairPrice Accuracy2 starsTrust Score*3 starsCancellation PolicyAirline Policy
Kiwi.comPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyNo Information

*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 October 25, 2024.

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.

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What is the cheapest month to book a flight from Oakland, California to Chicago?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $232). Flying from Oakland, California to Chicago in June is currently the most expensive (average of $308). 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 October 31, 2024.

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 25% 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 October 27, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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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 October 31, 2024.
Peruse reviews from past customers who have flown with Delta, Spirit Airlines and Frontier 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
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Volaris
6.7
Okay
1,313 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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
8,190 reviews
Southwest
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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 are 0 daily outbound flights to Chicago from 5 different airlines.

  • Can I find flights from Oakland, California to Chicago for under $100 on Cheapflights?

    Yes, there are multiple flights from Oakland, California to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $100, but on average you can expect to pay $422.

  • Are there nonstop flights from Oakland, California to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 1 direct flight from Oakland, California to Chicago under $300. A good price for a nonstop flight from Oakland, California to Chicago is less than $258.

  • Are there last-minute flights available from Oakland, California to Chicago for under $300?

    There are currently 10+ open flights from Oakland, California to Chicago within the next 7 days for less than $300.

  • 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 $100. Other airlines that can offer you cheap pricing are Alaska Airlines, from $239, and Southwest, from $247. Users have found that Spirit Airlines is 64% 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 $109 and $121 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.

  • What does OAK to ORD mean?

    This is defined as Oakland Airport (OAK) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Oakland to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Oakland to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Oakland to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Oakland to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Oakland to Chicago that allow pets onboard?

    Many airlines flying from Oakland to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Oakland to Chicago?

    Yes, you can often find last-minute deals on Oakland to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Oakland, California to Chicago flight deals updated?

    The Oakland, California to Chicago flight deals you see on this page were last updated on 10/31.

  • What is the cheapest month to book a flight from Oakland, California to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $232). Flying from Oakland, California to Chicago in June is currently the most expensive (average of $308). 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

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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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$79Average$242FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$141Average$296FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$158Average$529FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$467FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$237Average$383FlexibilityNo cancel feeOn-time63%
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