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$59+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

April

Round-trip from

$235
(Mytrip)

One-way from

$59
(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, 30% potential price rise
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Best time to find cheap flights, 68% 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 November 20, 2024.

This Mytrip deal was found by Cheapflights users on 11/19. 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.
Thu 12/511:24 amOAK - ORD
2 stops16h 06mSpirit Airlines
Sun 12/86:33 pmORD - OAK
3 stops24h 18mSpirit Airlines
Deal found 11/19$235
This Southwest deal was found by Cheapflights users on 11/19. 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.
Wed 12/254:25 pmOAK - MDW
1 stop5h 50mSouthwest
Wed 1/89:40 amMDW - OAK
Nonstop4h 55mSouthwest
Deal found 11/19$267
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/43:00 pmOAK - ORD
3 stops21h 15mMultiple Airlines
Fri 12/69:32 pmORD - OAK
3 stops19h 08mMultiple Airlines
Deal found 11/19$293
This Delta deal was found by Cheapflights users on 11/19. 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 12/255:30 amOAK - MDW
2 stops9h 41mDelta
Wed 1/82:08 pmMDW - OAK
2 stops11h 48mDelta
Deal found 11/19$304
This Delta deal was found by Cheapflights users on 11/20. 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 12/1712:55 pmOAK - ORD
1 stop7h 08mDelta
Thu 12/197:05 pmORD - OAK
1 stop7h 15mDelta
Deal found 11/20$367
This Alaska Airlines deal was found by Cheapflights users on 11/20. 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 12/136:00 amOAK - ORD
1 stop15h 47mAlaska Airlines
Sun 12/156:32 amORD - OAK
1 stop28h 38mAlaska Airlines
Deal found 11/20$388
This Mytrip deal was found by Cheapflights users on 11/20. 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 12/216:36 pmOAK - RFD
1 stop15h 14mMultiple Airlines
Sun 12/2912:40 pmRFD - OAK
1 stop9h 50mMultiple Airlines
Deal found 11/20$657
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Sun 11/245:16 pmOAK - MDW
2 stops19h 08mMultiple Airlines
Tue 11/2612:31 pmMDW - OAK
2 stops12h 26mMultiple Airlines
Deal found 11/20$697
This Mytrip deal was found by Cheapflights users on 11/20. 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 12/45:59 pmOAK - MDW
1 stop12h 46mVolaris
Fri 12/67:55 pmMDW - OAK
2 stops20h 30mVolaris
Deal found 11/20$841

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 12/5

11:24 am-5:30 am

2 stops16h 06m

Chicago O'Hare Intl

Sun 12/8

6:33 pm-4:51 pm

3 stops24h 18m

$235

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/22

3:20 pm-11:10 pm

1 stop5h 50m

Chicago Midway

Sat 3/1

5:10 pm-8:00 pm

Nonstop4h 50m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/7

5:35 am-5:47 pm

2 stops10h 12m

Chicago Midway

Fri 1/10

10:57 am-11:56 pm

2 stops14h 59m

$286

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 12/4

3:00 pm-2:15 pm

3 stops21h 15m

Chicago O'Hare Intl

Fri 12/6

9:32 pm-2:40 pm

3 stops19h 08m

$293

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 2/22

8:32 pm-1:04 pm

1 stop14h 32m

Chicago O'Hare Intl

Sat 3/1

7:45 am-7:52 pm

1 stop14h 07m

$294

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/17

12:55 pm-10:03 pm

1 stop7h 08m

Chicago O'Hare Intl

Thu 12/19

7:05 pm-12:20 am

1 stop7h 15m

$367

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 1/13

6:32 am-12:13 am

2 stops15h 41m

Chicago Midway

Sun 1/19

7:15 am-10:39 pm

2 stops17h 24m

$404

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 3/15

5:15 am-4:25 pm

1 stop9h 10m

Chicago O'Hare Intl

Tue 3/18

6:00 am-11:00 am

1 stop7h 00m

$416

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 3/17

11:59 pm-7:14 pm

1 stop17h 15m

Chicago Midway

Wed 3/19

8:39 pm-3:25 pm

2 stops20h 46m

$623

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Sat 12/21

6:36 pm-11:50 am

1 stop15h 14m

Chicago Greater Rockford

Sun 12/29

12:40 pm-8:30 pm

1 stop9h 50m

$657

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 November.
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*1 star
CheapOairPrice Accuracy2 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.

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 November 15, 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.

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 November 20, 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 November 18, 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.

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 November 20, 2024.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Spirit Airlines 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
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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
8,174 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.2

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 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 $235. Other airlines that can offer you cheap pricing are Southwest, from $237, and Delta, from $286. Users have found that Spirit Airlines is 20% 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 $59. Users have also found prices from $108 and $128 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, 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$242FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$293FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$416FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$467FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$379FlexibilityNo cancel feeOn-time63%
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