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$56+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Monday or Sunday and return on a Monday

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 12, 2025.

Round-trip from

$204
(Southwest)

One-way from

$56
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$371

Good round-trip deal

$364 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 ($55 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 6/302:05 pmOAK - ORD
1 stop7h 35mSouthwest
Fri 7/46:15 amORD - OAK
2 stops10h 10mSouthwest
Deal found 6/10$204
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 9/101:08 pmOAK - ORD
2 stops8h 35mSpirit Airlines
Mon 9/226:00 amORD - OAK
2 stops8h 13mSpirit Airlines
Deal found 6/10$205
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 8/52:38 pmOAK - ORD
1 stop7h 21mAlaska Airlines
Wed 8/66:00 amORD - OAK
1 stop9h 43mAlaska Airlines
Deal found 6/10$216
This Southwest deal was found by Cheapflights users on 6/10. 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 7/79:15 pmOAK - MDW
1 stop5h 45mSouthwest
Sat 7/127:50 amMDW - OAK
1 stop6h 15mSouthwest
Deal found 6/10$227
This Booking.com deal was found by Cheapflights users on 6/10. 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 7/106:00 amOAK - ORD
1 stop6h 13mMultiple Airlines
Thu 7/176:00 amORD - OAK
1 stop13h 15mMultiple Airlines
Deal found 6/10$236
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 8/912:30 pmOAK - ORD
1 stop7h 38mDelta
Wed 8/137:45 amORD - OAK
1 stop6h 10mDelta
Deal found 6/11$257
This Delta deal was found by Cheapflights users on 6/11. 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 7/224:55 pmOAK - MDW
2 stops13h 49mDelta
Tue 7/2912:43 pmMDW - OAK
2 stops13h 12mDelta
Deal found 6/11$267
This Mytrip deal was found by Cheapflights users on 6/11. 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 8/76:00 amOAK - RFD
2 stops28h 10mMultiple Airlines
Sun 8/1012:44 pmRFD - OAK
1 stop21h 44mMultiple Airlines
Deal found 6/11$316
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/296:00 amOAK - MDW
3 stops31h 37mMultiple Airlines
Sun 8/38:14 pmMDW - OAK
2 stops19h 29mMultiple Airlines
Deal found 6/10$466

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 June 12, 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

Mon 6/30

2:05 pm-11:40 pm

1 stop7h 35m

Chicago O'Hare Intl

Fri 7/4

6:15 am-2:25 pm

2 stops10h 10m

$204

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

1:08 pm-11:43 pm

2 stops8h 35m

Chicago O'Hare Intl

Mon 9/22

6:00 am-12:13 pm

2 stops8h 13m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 8/5

2:38 pm-11:59 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 8/6

6:00 am-1:43 pm

1 stop9h 43m

$216

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 7/7

9:15 pm-5:00 am

1 stop5h 45m

Chicago Midway

Sat 7/12

7:50 am-12:05 pm

1 stop6h 15m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/10

6:00 am-2:13 pm

1 stop6h 13m

Chicago O'Hare Intl

Thu 7/17

6:00 am-5:15 pm

1 stop13h 15m

$236

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 8/9

12:30 pm-10:08 pm

1 stop7h 38m

Chicago O'Hare Intl

Wed 8/13

7:45 am-11:55 am

1 stop6h 10m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 7/22

4:55 pm-8:44 am

2 stops13h 49m

Chicago Midway

Tue 7/29

12:43 pm-11:55 pm

2 stops13h 12m

$267

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Thu 8/7

6:00 am-12:10 pm

2 stops28h 10m

Chicago Greater Rockford

Sun 8/10

12:44 pm-8:28 am

1 stop21h 44m

$316

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 7/29

6:00 am-3:37 pm

3 stops31h 37m

Chicago Midway

Sun 8/3

8:14 pm-1:43 pm

2 stops19h 29m

$466

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 7/1

9:38 pm-6:12 am

1 stop6h 34m

$56

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 20 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 9, 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 June 12, 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 8, 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.

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 June 12, 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 compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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
345 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

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 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 $204. Other airlines that can offer you cheap pricing are Spirit Airlines, from $205, and Alaska Airlines, from $216. Users have found that Southwest is 40% 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 $56. Users have also found prices from $95 and $111 on Southwest and Sun Country Air, 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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Alternative routes for Oakland to Chicago

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$262FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$356FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$163Average$257FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$418FlexibilityNo cancel feeOn-time63%

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