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Cheap flights from Oakland (OAK) to Chicago (CHI) from $77

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
OAK — CHI
Jun 18 — Jun 251
From?
To?
Tue 6/18
Tue 6/25
1 adult, Economy
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The best prices from Oakland to Chicago are usually found in April or March, booked 8 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 June 13, 2024.

Popular in

June

Cheapest in

April

Round-trip from

$222

One-way from

$98
High demand for flights, 33% 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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What is the cheapest day to fly round-trip from Oakland, California to Chicago?

Flying to your destination on a Monday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Oakland, California to Chicago?

Find a great deal and save up to 43% by booking at least 47 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Oakland, California to Chicago within the next two weeks, with the cheapest ticket starting at $322.

What is the cheapest month to fly from Oakland, California to Chicago?

The best pricing can be found in the month of September. Prices to Chicago from Oakland, California average $316. You can even find prices in September for less than $316, as users have found deals to Chicago from as low as $100. The month of March appears to be one of the more expensive times to travel to Chicago from Oakland, California. Flying in the targeted month can save you up to 19%.

What is the cheapest time of day to fly from OAK to CHI?

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 14% on airfare.

Cheap Oakland to Chicago flights in June & July 2024

Find cheap flight options from Oakland to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,214,720 searches. Prices were last updated on June 13, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Tue 7/305:15 amOAK - ORD
1 stop10h 14mSpirit Airlines
Mon 8/1911:10 pmORD - OAK
1 stop12h 14mSpirit Airlines
Deal found 6/12$170
Tue 7/165:15 amOAK - ORD
1 stop10h 14mSpirit Airlines
Tue 7/236:19 pmORD - OAK
1 stop6h 17mSpirit Airlines
Deal found 6/11$177
Mon 7/298:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Wed 7/317:01 amORD - OAK
2 stops18h 05mSpirit Airlines
Deal found 6/12$178
Tue 7/2310:05 pmOAK - ORD
1 stop6h 31mSpirit Airlines
Tue 7/306:19 pmORD - OAK
1 stop6h 17mSpirit Airlines
Deal found 6/13$180
Mon 7/158:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Wed 7/171:28 pmORD - OAK
1 stop8h 23mSpirit Airlines
Deal found 6/12$181
Wed 7/105:15 amOAK - ORD
1 stop15h 04mSpirit Airlines
Wed 7/171:28 pmORD - OAK
1 stop11h 38mSpirit Airlines
Deal found 6/13$187
Tue 7/99:29 pmOAK - ORD
1 stop7h 07mSpirit Airlines
Wed 7/171:28 pmORD - OAK
1 stop9h 32mSpirit Airlines
Deal found 6/13$188
Wed 7/105:15 amOAK - ORD
1 stop10h 14mSpirit Airlines
Wed 7/179:19 amORD - OAK
1 stop12h 32mSpirit Airlines
Deal found 6/13$190
Sun 7/1411:59 pmOAK - ORD
1 stop17h 11mSun Country Air
Thu 7/187:00 amORD - OAK
1 stop12h 07mSun Country Air
Deal found 6/13$191

Oakland to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Oakland and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,214,720 searches. Data last updated June 13, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Mon 8/128:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Tue 8/279:10 amORD - OAK
1 stop15h 42mSpirit Airlines
Deal found 6/11$161
Wed 8/286:05 amOAK - ORD
1 stop10h 43mSpirit Airlines
Mon 9/911:10 pmORD - OAK
1 stop12h 14mSpirit Airlines
Deal found 6/13$163
Wed 8/286:05 amOAK - ORD
1 stop10h 43mSpirit Airlines
Wed 9/48:37 amORD - OAK
1 stop10h 26mSpirit Airlines
Deal found 6/13$165
Mon 8/58:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Wed 8/76:19 pmORD - OAK
1 stop6h 47mSpirit Airlines
Deal found 6/11$169
Tue 7/305:15 amOAK - ORD
1 stop10h 14mSpirit Airlines
Mon 8/1911:10 pmORD - OAK
1 stop12h 14mSpirit Airlines
Deal found 6/12$170
Wed 8/214:50 pmOAK - ORD
1 stop10h 39mSpirit Airlines
Mon 8/2611:10 pmORD - OAK
1 stop12h 14mSpirit Airlines
Deal found 6/12$172
Wed 8/286:05 amOAK - ORD
1 stop10h 43mSpirit Airlines
Mon 9/911:10 pmORD - OAK
2 stops20h 39mSpirit Airlines
Deal found 6/13$175
Tue 7/165:15 amOAK - ORD
1 stop10h 14mSpirit Airlines
Tue 7/236:19 pmORD - OAK
1 stop6h 17mSpirit Airlines
Deal found 6/11$177
Mon 7/298:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Wed 7/317:01 amORD - OAK
2 stops18h 05mSpirit Airlines
Deal found 6/12$178

Oakland to Chicago flights leaving soon

Find last-minute flight options from Oakland to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,214,720 searches. Data last updated June 13, 2024.
Users seeking a last-minute flight from Oakland to Chicago should consider booking one of these fares. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Tue 6/259:29 pmOAK - ORD
1 stop7h 07mSpirit Airlines
Tue 7/210:01 pmORD - OAK
1 stop15h 11mSpirit Airlines
Deal found 6/13$188
Tue 6/259:29 pmOAK - ORD
1 stop7h 07mSpirit Airlines
Thu 6/2710:17 pmORD - OAK
1 stop10h 25mSpirit Airlines
Deal found 6/12$201
Tue 6/255:39 pmOAK - ORD
1 stop10h 57mSpirit Airlines
Tue 7/210:01 pmORD - OAK
2 stops16h 24mSpirit Airlines
Deal found 6/13$204
Wed 6/269:22 pmOAK - ORD
1 stop7h 02mSpirit Airlines
Tue 7/29:36 amORD - OAK
1 stop15h 06mSpirit Airlines
Deal found 6/12$205
Tue 6/259:29 pmOAK - ORD
1 stop7h 07mSpirit Airlines
Thu 6/2710:17 pmORD - OAK
1 stop10h 25mSpirit Airlines
Deal found 6/12$206
Wed 6/269:22 pmOAK - ORD
1 stop7h 02mSpirit Airlines
Mon 7/110:17 pmORD - OAK
1 stop12h 14mSpirit Airlines
Deal found 6/12$207
Wed 6/269:22 pmOAK - ORD
1 stop7h 02mSpirit Airlines
Mon 7/19:54 amORD - OAK
1 stop15h 09mSpirit Airlines
Deal found 6/13$209
Wed 6/269:22 pmOAK - ORD
1 stop7h 02mSpirit Airlines
Tue 7/210:01 pmORD - OAK
1 stop15h 11mSpirit Airlines
Deal found 6/12$211
Wed 6/269:22 pmOAK - ORD
1 stop7h 02mSpirit Airlines
Tue 7/210:01 pmORD - OAK
1 stop15h 11mSpirit Airlines
Deal found 6/12$212

One-way flights to Chicago from Oakland

Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,214,720 searches. Data last updated June 13, 2024.
Users traveling one-way from Oakland to Chicago can select one of these great deals. Users needing a return flight from Oakland to Chicago should utilize the search form above.
Wed 9/115:20 amOAK - ORD
1 stop10h 43mSpirit Airlines
Deal found 6/12$77
Wed 8/75:30 amOAK - RFD
1 stop7h 20mMultiple Airlines
Deal found 6/11$79
Sat 7/205:30 amOAK - RFD
1 stop8h 20mMultiple Airlines
Deal found 6/13$82
Tue 7/3010:05 pmOAK - ORD
1 stop6h 31mSpirit Airlines
Deal found 6/12$84
Mon 7/89:21 pmOAK - ORD
1 stop7h 15mSpirit Airlines
Deal found 6/12$85
Mon 7/81:15 pmOAK - ORD
1 stop15h 21mSpirit Airlines
Deal found 6/12$86
Mon 7/158:57 pmOAK - ORD
1 stop7h 45mSpirit Airlines
Deal found 6/12$88
Mon 8/264:50 pmOAK - ORD
3 stops29h 05mSpirit Airlines
Deal found 6/12$92
Tue 6/255:39 pmOAK - ORD
1 stop10h 57mSpirit Airlines
Deal found 6/12$94

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 3,214,720 searches. Data last updated June 13, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$161 - $236

Route

Depart

Return

Price

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Mon 8/12

1 stop7h 45m

Chicago O'Hare Intl

Tue 8/27

1 stop15h 42m

$161

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Wed 8/28

1 stop10h 43m

Chicago O'Hare Intl

Mon 9/9

1 stop12h 14m

$163

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Wed 8/28

1 stop10h 43m

Chicago O'Hare Intl

Wed 9/4

1 stop10h 26m

$165

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Mon 8/5

1 stop7h 45m

Chicago O'Hare Intl

Wed 8/7

1 stop6h 47m

$169

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Tue 7/30

1 stop10h 14m

Chicago O'Hare Intl

Mon 8/19

1 stop12h 14m

$170

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Sun 7/14

1 stop17h 11m

Chicago O'Hare Intl

Thu 7/18

1 stop12h 07m

$191

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Sun 7/14

1 stop17h 11m

Chicago O'Hare Intl

Tue 7/16

1 stop6h 17m

$192

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Tue 7/2

1 stop16h 58m

Chicago O'Hare Intl

Mon 7/8

2 stops27h 35m

$218

OaklandChicago O'Hare Intl

OAK - ORD

OAKORD

Oakland

Sat 8/17

1 stop7h 20m

Chicago O'Hare Intl

Tue 8/20

1 stop6h 21m

$236

Flights are sorted by cheapest first

Deals found on 6/11

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 June 12, 2024.
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.
Search Deals

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 June 9, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Chicago by month

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

CHI

Temperature

23 - 73.4 °F

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 June 13, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Delta 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.
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Alaska Airlines
8.1
Very good
9,272 reviews
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Delta
8.0
Very good
10,000 reviews
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Sun Country Air
7.3
Good
579 reviews
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Volaris
6.6
Okay
1,452 reviews
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Spirit Airlines
6.4
Okay
8,537 reviews
Alaska Airlines
8.1
Very good
9,272 reviews

Crew

8.6

Overall

8.1

Boarding

8.2

Entertainment

7.3

Comfort

7.9

Food

7.3

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

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 7 daily outbound flights to Chicago from 6 different airlines.

  • Can I find flights from Oakland, California to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Oakland, California to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $161, but on average you can expect to pay $178.

  • Are there last-minute flights available from Oakland, California to Chicago for under $200?

    There are currently 20+ open flights from Oakland, California to Chicago within the next 7 days for less than $200.

  • 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 $161. Another airline that can offer you cheap pricing is Sun Country Air. Users have found that Spirit Airlines is 43% cheaper than the other options available to this destination.

  • 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 6/13.

  • What are the most popular airlines that fly from Oakland, California to Chicago?

    American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Oakland, California to Chicago.

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

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $244). Flying from Oakland, California to Chicago in July 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

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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 6 airlines flying from Oakland to Chicago

Discover the top 6 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 3,214,720 searches. Data last updated June 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$167FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$153Average$365FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$158Average$289FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$181Average$394FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$430FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$421FlexibilityNo cancel feeOn-timeN/A
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Washington, D.C. to Chicago flights
Boston to New York flights
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Oakland, California to Charlottesville flights

Search flights from Oakland to Chicago by cabin class

Find flights from Oakland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Oakland to Chicago

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 June 13, 2024.
24%of flight departuresEarly morningMidnight to 6 am
32%of flight departuresMorning6 am to noon
44%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Oakland 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 June 13, 2024.
Sunday4daily flights
Monday10daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday10daily flights
Friday10daily flights
Saturday4daily flights

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