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$62+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Jul 9 — Jul 161
Wed 7/9
Wed 7/16
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in September or August, booked 47 days in advance, depart on a Wednesday or Monday 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 July 4, 2025.

Round-trip from

$198
(Booking.com)

One-way from

$62
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$324

Good round-trip deal

$417 or less

Good one-way deal

$228 or less
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. 14% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 4, 2025.

This Booking.com deal was found by Cheapflights users on 7/3. 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 7/242:38 pmOAK - ORD
2 stops13h 25mSpirit Airlines
Tue 7/293:18 pmORD - OAK
1 stop10h 15mSpirit Airlines
Deal found 7/3$198
This Southwest deal was found by Cheapflights users on 7/3. 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 8/105:50 amOAK - MDW
Nonstop4h 05mSouthwest
Sat 8/163:25 pmMDW - OAK
Nonstop4h 30mSouthwest
Deal found 7/3$207
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Thu 8/76:00 amOAK - ORD
1 stop6h 13mMultiple Airlines
Sun 8/109:56 pmORD - OAK
2 stops16h 31mMultiple Airlines
Deal found 7/1$211
This Mytrip deal was found by Cheapflights users on 7/3. 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 9/46:00 amOAK - RFD
1 stop10h 52mMultiple Airlines
Sun 9/79:16 pmRFD - OAK
1 stop11h 47mMultiple Airlines
Deal found 7/3$213
This Alaska Airlines deal was found by Cheapflights users on 7/1. 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 8/227:07 pmOAK - ORD
1 stop7h 53mAlaska Airlines
Wed 8/276:20 amORD - OAK
1 stop9h 16mAlaska Airlines
Deal found 7/1$226
This Southwest deal was found by Cheapflights users on 7/2. 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 7/276:05 amOAK - ORD
1 stop8h 40mSouthwest
Sat 8/96:15 amORD - OAK
1 stop8h 10mSouthwest
Deal found 7/2$227
This Delta deal was found by Cheapflights users on 7/3. 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 9/305:05 pmOAK - MDW
2 stops14h 35mDelta
Sat 10/41:43 pmMDW - OAK
2 stops11h 05mDelta
Deal found 7/3$267

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 July 4, 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

Thu 7/24

2:38 pm-6:03 am

2 stops13h 25m

Chicago O'Hare Intl

Tue 7/29

3:18 pm-11:33 pm

1 stop10h 15m

$198

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 8/10

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Sat 8/16

3:25 pm-5:55 pm

Nonstop4h 30m

$207

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 8/7

6:00 am-2:13 pm

1 stop6h 13m

Chicago O'Hare Intl

Sun 8/10

9:56 pm-12:27 pm

2 stops16h 31m

$211

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Thu 9/4

6:00 am-6:52 pm

1 stop10h 52m

Chicago Greater Rockford

Sun 9/7

9:16 pm-7:03 am

1 stop11h 47m

$213

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 8/22

7:07 pm-5:00 am

1 stop7h 53m

Chicago O'Hare Intl

Tue 8/26

8:00 am-1:36 pm

1 stop7h 36m

$226

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 7/27

6:05 am-4:45 pm

1 stop8h 40m

Chicago O'Hare Intl

Sat 8/9

6:15 am-12:25 pm

1 stop8h 10m

$227

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 9/30

5:05 pm-9:40 am

2 stops14h 35m

Chicago Midway

Sat 10/4

1:43 pm-10:48 pm

2 stops11h 05m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 8/9

6:00 am-2:13 pm

1 stop6h 13m

$62

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 8/31

8:15 am-2:20 pm

Nonstop4h 05m

$90

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 9/26

6:00 am-8:52 pm

1 stop12h 52m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 16 results
1
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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 June 27, 2025.

The best time to book flights from Oakland, California to Chicago is 47 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 $321). 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 July 4, 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 June 29, 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.

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 July 4, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oakland to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,270 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,970 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
339 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $198. Other airlines that can offer you cheap pricing are Southwest, from $207, and Alaska Airlines, from $226. Users have found that Spirit Airlines is 42% 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 $62. Users have also found prices from $90 and $104 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 $321). 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 July 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$104Average$257FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$356FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$163Average$279FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$413FlexibilityNo cancel feeOn-time63%

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