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 $255. Other airlines that can offer you cheap pricing are Delta, from $257, and Southwest, from $262. Users have found that Spirit Airlines is 18% 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 $99 and $108 on Southwest and Alaska Airlines, respectively.

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

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.

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

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

What is the cheapest day to fly round-trip from Oakland, California to Chicago?

Flying to your destination on a Sunday 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 73% by booking at least 35 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 $387.

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

The best pricing can be found in the month of February. Prices to Chicago from Oakland, California average $339. You can even find prices in February for less than $339, as users have found deals to Chicago from as low as $183. The month of December 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 28%.

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 eDreams the most. eDreams 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.

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.

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.

$59+ Flights from Oakland, CA to Chicago - Compare & Save Big

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from Oakland to Chicago are usually found in April or August, booked 8 days in advance, depart on a Sunday or Wednesday and return on a Thursday

Cheap flight deals from Oakland to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$255 (FlightHub)
One-way from	$59 (eDestinos)
Popular in	November
Cheapest in	April
Average price	$357
Good round-trip deal	$387 or less
Good one-way deal	$208 or less

Provider with most accurate pricing for Oakland-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Oakland-Chicago (CHI) flights.

Search Deals

From Oakland to Chicago (CHI)

Search Deals

One-way flight from Oakland to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 15% potential increase in price ($55 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

Search Deals

Price to beat on a round-trip flight from Oakland to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from Oakland to Chicago (CHI).

Search Deals

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 May 1, 2025.

Thu 6/129:38 pmOAK - ORD

1 stop6h 34mSpirit Airlines

Sun 6/159:35 pmORD - OAK

2 stops14h 01mSpirit Airlines

Deal found 4/30

$255

Mon 5/1910:36 amOAK - ORD

2 stops16h 49mMultiple Airlines

Sat 5/316:00 amORD - OAK

1 stop9h 36mMultiple Airlines

Deal found 4/30

$256

Fri 5/3012:39 pmOAK - ORD

1 stop7h 01mDelta

Sun 6/17:30 amORD - OAK

1 stop6h 26mDelta

Deal found 4/30

$257

Mon 6/25:05 amOAK - MDW

Nonstop4h 10mSouthwest

Thu 6/57:20 amMDW - OAK

Nonstop4h 30mSouthwest

Deal found 4/30

$262

Tue 6/36:00 amOAK - MDW

2 stops9h 45mDelta

Wed 6/119:21 amMDW - OAK

2 stops8h 55mDelta

Deal found 4/29

$267

Tue 5/207:00 amOAK - ORD

1 stop8h 02mHawaiian Airlines

Sat 5/316:00 amORD - OAK

1 stop8h 08mHawaiian Airlines

Deal found 4/30

$271

Tue 6/2412:49 pmOAK - ORD

1 stop9h 10mAlaska Airlines

Wed 7/26:00 amORD - OAK

1 stop9h 43mAlaska Airlines

Deal found 4/30

$275

Wed 5/145:45 amOAK - RFD

1 stop27h 53mMultiple Airlines

Sun 5/1812:28 pmRFD - OAK

1 stop11h 57mMultiple Airlines

Deal found 4/28

$286

Sat 8/3012:50 pmOAK - ORD

2 stops8h 15mSouthwest

Tue 9/26:15 amORD - OAK

1 stop9h 15mSouthwest

Deal found 4/29

$290

Thu 5/2911:51 amOAK - MDW

2 stops28h 19mMultiple Airlines

Mon 6/99:12 amMDW - OAK

2 stops27h 44mMultiple Airlines

Deal found 4/30

$306

Thu 7/311:59 pmOAK - ORD

1 stop10h 52mSun Country Air

Sun 7/66:15 pmORD - OAK

1 stop6h 36mSun Country Air

Deal found 4/30

$368

Best flights from Oakland to Chicago
Discover carefully curated flight deals from Oakland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Thu 6/129:38 pmOAK - ORD

1 stop6h 34mSpirit Airlines

Sun 6/159:35 pmORD - OAK

2 stops14h 01mSpirit Airlines

Deal found 4/30

$255

Mon 5/1910:36 amOAK - ORD

2 stops16h 49mMultiple Airlines

Sat 5/316:00 amORD - OAK

1 stop9h 36mMultiple Airlines

Deal found 4/30

$256

Fri 5/3012:39 pmOAK - ORD

1 stop7h 01mDelta

Wed 6/47:30 amORD - OAK

1 stop6h 26mDelta

Deal found 4/30

$257

Mon 6/25:05 amOAK - MDW

Nonstop4h 10mSouthwest

Tue 6/36:45 pmMDW - OAK

1 stop6h 30mSouthwest

Deal found 4/30

$262

Tue 5/207:00 amOAK - ORD

1 stop8h 02mHawaiian Airlines

Sat 5/316:00 amORD - OAK

1 stop8h 08mHawaiian Airlines

Deal found 4/30

$271

Tue 6/2412:49 pmOAK - ORD

1 stop9h 10mAlaska Airlines

Wed 7/26:00 amORD - OAK

1 stop9h 43mAlaska Airlines

Deal found 4/30

$275

Thu 7/311:59 pmOAK - ORD

1 stop10h 52mSun Country Air

Sun 7/66:15 pmORD - OAK

1 stop6h 36mSun Country Air

Deal found 4/30

$368

Wed 6/254:58 pmOAK - MDW

2 stops13h 43mDelta

Tue 7/11:09 pmMDW - OAK

2 stops11h 19mDelta

Deal found 4/30

$267

Wed 5/145:45 amOAK - RFD

1 stop27h 53mMultiple Airlines

Sun 5/1812:28 pmRFD - OAK

1 stop11h 57mMultiple Airlines

Deal found 4/28

$286

Sat 8/3012:50 pmOAK - ORD

2 stops8h 15mSouthwest

Tue 9/26:15 amORD - OAK

1 stop9h 15mSouthwest

Deal found 4/29

$290

Thu 5/2911:51 amOAK - MDW

2 stops28h 19mMultiple Airlines

Mon 6/99:12 amMDW - OAK

2 stops39h 13mMultiple Airlines

Deal found 4/30

$314

Last-minute flights from Oakland to Chicago
Discover last-minute flight deals from Oakland to Chicago. Data last updated May 1, 2025 and is based on user searches.

Mon 5/55:05 amOAK - MDW

Nonstop4h 10mSouthwest

Fri 5/99:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 4/29

$381

Tue 5/65:10 pmOAK - ORD

1 stop5h 43mDelta

Fri 5/97:30 amORD - OAK

1 stop6h 26mDelta

Deal found 4/30

$979

Wed 5/79:09 pmOAK - ORD

1 stop6h 16mSpirit Airlines

Mon 5/129:02 pmORD - OAK

1 stop15h 54mSpirit Airlines

Deal found 4/29

$257

Wed 5/79:09 pmOAK - ORD

1 stop6h 16mMultiple Airlines

Sat 5/105:56 pmORD - OAK

1 stop7h 48mMultiple Airlines

Deal found 4/30

$350

Wed 5/76:00 amOAK - MDW

2 stops10h 45mDelta

Sat 5/101:55 pmMDW - OAK

2 stops10h 35mDelta

Deal found 4/30

$411

Thu 5/86:00 amOAK - ORD

1 stop9h 00mAlaska Airlines

Thu 5/87:19 pmORD - OAK

1 stop27h 57mAlaska Airlines

Deal found 4/30

$600

Fri 5/96:25 amOAK - ORD

2 stops8h 20mSouthwest

Tue 5/1312:40 pmORD - OAK

2 stops9h 00mSouthwest

Deal found 4/30

$499

Wed 5/145:45 amOAK - RFD

1 stop27h 53mMultiple Airlines

Sun 5/1812:28 pmRFD - OAK

1 stop11h 57mMultiple Airlines

Deal found 4/28

$286

Thu 5/155:00 amOAK - ORD

1 stop8h 00mSouthwest

Mon 5/195:45 pmORD - OAK

1 stop7h 00mSouthwest

Deal found 4/30

$453

Mon 5/1910:36 amOAK - ORD

2 stops16h 49mMultiple Airlines

Sat 5/316:00 amORD - OAK

1 stop9h 36mMultiple Airlines

Deal found 4/30

$256

Tue 5/207:00 amOAK - ORD

1 stop8h 02mHawaiian Airlines

Sat 5/316:00 amORD - OAK

1 stop8h 08mHawaiian Airlines

Deal found 4/30

$271

Mon 5/265:05 amOAK - MDW

Nonstop4h 10mSouthwest

Sat 5/315:20 amMDW - OAK

2 stops8h 50mSouthwest

Deal found 4/29

$272

One-way flights from Oakland to Chicago
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Thu 5/2910:36 amOAK - ORD

2 stops16h 49mSpirit Airlines

Deal found 4/29

$59

Tue 6/35:50 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 4/29

$99

Sat 5/311:40 pmOAK - ORD

2 stops8h 00mSouthwest

Deal found 4/30

$105

Tue 6/102:31 pmOAK - ORD

1 stop7h 28mAlaska Airlines

Deal found 4/30

$108

Sun 6/811:51 amOAK - MDW

1 stop25h 05mMultiple Airlines

Deal found 4/30

$113

Tue 7/112:30 pmOAK - ORD

1 stop7h 39mDelta

Deal found 5/1

$129

Tue 6/36:00 amOAK - MDW

2 stops9h 45mDelta

Deal found 4/29

$134

Mon 7/217:58 pmOAK - ORD

1 stop7h 42mHawaiian Airlines

Deal found 4/30

$138

Sun 8/315:29 pmOAK - ORD

1 stop14h 19mSun Country Air

Deal found 4/30

$140

Wed 6/255:30 amOAK - ORD

3 stops30h 45mMultiple Airlines

Deal found 4/30

$187

Cheapflights Fare Finder

Use the filters below to find and compare flights from Oakland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 6/12

9:38 pm-6:12 am

1 stop6h 34m

Chicago O'Hare Intl

Sun 6/15

9:35 pm-9:36 am

2 stops14h 01m

$255

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 5/19

10:36 am-5:25 am

2 stops16h 49m

Chicago O'Hare Intl

Sat 5/31

6:00 am-1:36 pm

1 stop9h 36m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 5/30

12:39 pm-9:40 pm

1 stop7h 01m

Chicago O'Hare Intl

Wed 6/4

7:30 am-11:56 am

1 stop6h 26m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 6/2

5:05 am-11:15 am

Nonstop4h 10m

Chicago Midway

Thu 6/5

7:20 am-9:50 am

Nonstop4h 30m

$262

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 6/25

4:58 pm-8:41 am

2 stops13h 43m

Chicago Midway

Tue 7/1

1:09 pm-10:28 pm

2 stops11h 19m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/20

7:00 am-5:02 pm

1 stop8h 02m

Chicago O'Hare Intl

Sat 5/31

6:00 am-12:08 pm

1 stop8h 08m

$271

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 6/24

12:49 pm-11:59 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 7/2

6:00 am-1:43 pm

1 stop9h 43m

$275

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 5/29

11:51 am-6:10 pm

2 stops28h 19m

Chicago Midway

Mon 6/9

9:12 am-10:25 pm

2 stops39h 13m

$314

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/3

11:59 pm-12:51 pm

1 stop10h 52m

Chicago O'Hare Intl

Sun 7/6

6:15 pm-10:51 pm

1 stop6h 36m

$368

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/3

5:05 am-3:00 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 7/5

4:00 pm-9:50 pm

1 stop7h 50m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 20 results

Compare providers for flights from Oakland to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Chicago in May.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy2 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 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 eDreams the most. eDreams 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.

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?

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.

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?

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.

Rainfall in Chicago 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

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

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

9,968 reviews

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

9,968 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

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

4,294 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

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

7,934 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

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

2,408 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

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

346 reviews

Alaska Airlines

8.0

Very good

9,968 reviews

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

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 $255. Other airlines that can offer you cheap pricing are Delta, from $257, and Southwest, from $262. Users have found that Spirit Airlines is 18% 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 $99 and $108 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

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Top 5 airlines flying from Oakland to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$123	Average$287	FlexibilityNo cancel fee	On-time65%
Alaska Airlines	Cheapest$138	Average$356	FlexibilityNo cancel fee	On-time75%
United Airlines	Cheapest$185	Average$257	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$235	Average$360	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$263	Average$423	FlexibilityNo cancel fee	On-time63%

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$59+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Oakland to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Oakland to Chicago are usually found in April or August, booked 8 days in advance, depart on a Sunday or Wednesday and return on a Thursday

Cheap flight deals from Oakland to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Oakland to Chicago

Cheapest flights from Oakland to ChicagoExplore 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 May 1, 2025.

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 May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Oakland to Chicago that are best for you.

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 May.

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.

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 April 25, 2025.

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

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 May 1, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

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 May 1, 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.

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?

What are the cheapest airlines flying from Oakland, California to Chicago round-trip?

What are the cheapest airlines to fly from Oakland, California to Chicago one-way?

What are the most popular routes from Oakland, California to Chicago?

Can I find deals for flights from Oakland to Chicago that include hotel bookings?

How can I find direct flights from Oakland to Chicago?

Can I find deals for business class flights from Oakland to Chicago?

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

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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 May 1, 2025.