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 $118. Other airlines that can offer you cheap pricing are Southwest, from $227, and Delta, from $253. Users have found that Spirit Airlines is 62% 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 $57. Users have also found prices from $99 and $129 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.

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 Saturday 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 77% by booking at least 42 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 $404.

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 $342. You can even find prices in February for less than $342, 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 27%.

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.

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 4 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.

$57+ Flights from Oakland, CA to Chicago

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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.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Oakland to Chicago are usually found in April or August, booked 89 days in advance, depart on a Friday or Saturday and return on a Thursday

Cheap flight deals from Oakland to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$118 (Expedia)
One-way from	$57 (FlightHub)
Popular in	June
Cheapest in	April
Average price	$329
Good round-trip deal	$406 or less
Good one-way deal	$238 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. 10% potential increase in price ($35 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in February 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 febrero 20, 2025.

lun. 3/105:52 pmOAK - ORD

1 stop10h 50mSpirit Airlines

mié. 3/1210:49 amORD - OAK

1 stop8h 08mSpirit Airlines

Deal found 2/19

$118

mar. 5/65:50 amOAK - MDW

Nonstop4h 10mSouthwest

vie. 5/99:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 2/19

$227

sáb. 3/156:00 amOAK - ORD

1 stop5h 52mDelta

mar. 3/187:15 pmORD - OAK

1 stop6h 44mDelta

Deal found 2/20

$257

vie. 9/2610:45 pmOAK - MDW

1 stop8h 33mDelta

sáb. 10/41:05 pmMDW - OAK

1 stop10h 27mDelta

Deal found 2/19

$288

jue. 5/87:30 amOAK - RFD

1 stop11h 16mMultiple Airlines

dom. 5/119:36 pmRFD - OAK

1 stop24h 38mMultiple Airlines

Deal found 2/20

$290

vie. 2/286:49 amOAK - ORD

1 stop9h 11mMultiple Airlines

mié. 3/57:47 amORD - OAK

1 stop11h 10mMultiple Airlines

Deal found 2/19

$302

mar. 3/115:40 amOAK - ORD

1 stop9h 05mSouthwest

sáb. 3/158:00 pmORD - OAK

1 stop6h 30mSouthwest

Deal found 2/19

$322

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 febrero 20, 2025.

lun. 4/76:55 pmOAK - ORD

1 stop9h 47mSpirit Airlines

mié. 4/97:41 amORD - OAK

1 stop11h 53mSpirit Airlines

Deal found 2/20

$118

mar. 5/65:50 amOAK - MDW

Nonstop4h 10mSouthwest

vie. 5/99:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 2/19

$227

mar. 3/2512:55 pmOAK - ORD

1 stop6h 50mDelta

vie. 3/287:15 pmORD - OAK

1 stop6h 44mDelta

Deal found 2/20

$253

jue. 3/277:31 amOAK - ORD

3 stops28h 44mMultiple Airlines

mar. 4/12:34 pmORD - OAK

2 stops23h 43mMultiple Airlines

Deal found 2/20

$277

mié. 6/48:00 amOAK - ORD

1 stop13h 56mAlaska Airlines

mar. 6/107:00 amORD - OAK

1 stop14h 14mAlaska Airlines

Deal found 2/20

$332

jue. 5/87:30 amOAK - RFD

1 stop11h 16mMultiple Airlines

dom. 5/119:36 pmRFD - OAK

1 stop24h 38mMultiple Airlines

Deal found 2/20

$290

mar. 3/255:35 amOAK - ORD

1 stop7h 25mSouthwest

jue. 3/276:00 amORD - OAK

1 stop8h 30mSouthwest

Deal found 2/20

$306

mar. 3/185:15 pmOAK - MDW

2 stops13h 54mDelta

sáb. 3/291:12 pmMDW - OAK

2 stops11h 25mDelta

Deal found 2/19

$358

Last-minute flights from Oakland to Chicago
Discover last-minute flight deals from Oakland to Chicago. Data last updated febrero 20, 2025 and is based on user searches.

jue. 2/276:49 amOAK - ORD

1 stop9h 11mAlaska Airlines

jue. 3/135:54 pmORD - OAK

1 stop7h 49mAlaska Airlines

Deal found 2/20

$411

vie. 2/286:49 amOAK - ORD

1 stop9h 11mMultiple Airlines

mié. 3/57:47 amORD - OAK

1 stop11h 10mMultiple Airlines

Deal found 2/19

$302

vie. 2/286:05 amOAK - MDW

1 stop7h 00mSouthwest

mié. 3/58:30 amMDW - OAK

1 stop7h 00mSouthwest

Deal found 2/19

$358

sáb. 3/15:10 amOAK - ORD

2 stops28h 32mSpirit Airlines

lun. 3/172:42 pmORD - OAK

1 stop28h 15mSpirit Airlines

Deal found 2/20

$308

sáb. 3/15:00 amOAK - ORD

1 stop7h 00mSouthwest

vie. 3/142:50 pmORD - OAK

1 stop9h 20mSouthwest

Deal found 2/20

$392

sáb. 3/11:15 pmOAK - ORD

1 stop6h 12mDelta

lun. 3/37:18 pmORD - OAK

1 stop6h 38mDelta

Deal found 2/20

$417

sáb. 3/16:00 amOAK - MDW

2 stops9h 43mDelta

mar. 3/41:26 pmMDW - OAK

2 stops12h 30mDelta

Deal found 2/20

$427

jue. 3/66:49 amOAK - ORD

1 stop9h 11mAlaska Airlines

lun. 3/105:54 pmORD - OAK

1 stop7h 49mAlaska Airlines

Deal found 2/19

$336

lun. 3/105:52 pmOAK - ORD

1 stop10h 50mSpirit Airlines

mié. 3/1210:49 amORD - OAK

1 stop8h 08mSpirit Airlines

Deal found 2/19

$118

mar. 3/115:40 amOAK - ORD

1 stop9h 05mSouthwest

sáb. 3/158:00 pmORD - OAK

1 stop6h 30mSouthwest

Deal found 2/19

$322

sáb. 3/156:00 amOAK - ORD

1 stop5h 52mDelta

mar. 3/187:15 pmORD - OAK

1 stop6h 44mDelta

Deal found 2/20

$257

sáb. 3/152:40 pmOAK - MDW

1 stop6h 50mSouthwest

lun. 3/177:55 pmMDW - OAK

1 stop6h 40mSouthwest

Deal found 2/20

$302

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 febrero 20, 2025.

lun. 4/146:29 pmOAK - ORD

1 stop10h 04mSpirit Airlines

Deal found 2/20

$57

mar. 4/295:50 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 2/19

$99

sáb. 4/265:10 pmOAK - ORD

1 stop5h 43mDelta

Deal found 2/20

$129

sáb. 4/196:00 amOAK - MDW

2 stops9h 19mDelta

Deal found 2/19

$134

jue. 4/1712:58 pmOAK - MDW

2 stops19h 11mMultiple Airlines

Deal found 2/19

$135

jue. 3/207:31 amOAK - RFD

1 stop11h 16mMultiple Airlines

Deal found 2/19

$146

jue. 6/195:50 pmOAK - ORD

1 stop23h 21mSun Country Air

Deal found 2/20

$166

jue. 2/275:20 amOAK - ORD

1 stop7h 05mSouthwest

Deal found 2/20

$183

sáb. 6/216:45 pmOAK - ORD

1 stop8h 19mHawaiian Airlines

Deal found 2/20

$193

vie. 3/76:49 amOAK - ORD

1 stop9h 11mAlaska Airlines

Deal found 2/20

$194

Find flights from Oakland to Chicago within your budget

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

lun. 4/7

6:55 pm-6:42 am

1 stop9h 47m

Chicago O'Hare Intl

mié. 4/9

7:41 am-5:34 pm

1 stop11h 53m

$118

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mar. 5/6

5:50 am-12:00 pm

Nonstop4h 10m

Chicago Midway

vie. 5/9

9:10 pm-11:45 pm

Nonstop4h 35m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 3/25

12:55 pm-9:45 pm

1 stop6h 50m

Chicago O'Hare Intl

vie. 3/28

7:15 pm-11:59 pm

1 stop6h 44m

$253

OaklandChicago

OAK - ORD

OAKORD

Oakland

jue. 3/27

7:31 am-2:15 pm

3 stops28h 44m

Chicago O'Hare Intl

mar. 4/1

2:34 pm-12:17 pm

2 stops23h 43m

$277

OaklandChicago

OAK - RFD

OAKRFD

Oakland

jue. 5/8

7:30 am-8:46 pm

1 stop11h 16m

Chicago Greater Rockford

dom. 5/11

9:36 pm-8:14 pm

1 stop24h 38m

$290

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mar. 3/18

5:15 pm-9:09 am

2 stops13h 54m

Chicago Midway

sáb. 3/29

1:12 pm-10:37 pm

2 stops11h 25m

$358

OaklandChicago

OAK - ORD

OAKORD

Oakland

lun. 3/24

6:55 pm-6:42 am

1 stop9h 47m

$57

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mar. 4/29

5:50 am-12:00 pm

Nonstop4h 10m

$99

OaklandChicago

OAK - ORD

OAKORD

Oakland

sáb. 5/3

5:10 pm-12:53 am

1 stop5h 43m

$129

OaklandChicago

OAK - MDW

OAKMDW

Oakland

sáb. 4/19

6:00 am-5:19 pm

2 stops9h 19m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 16 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 February.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	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 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?

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, 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.

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.

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 Southwest, Alaska Airlines 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.

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

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

4,411 reviews

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

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

9,697 reviews

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

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

8,219 reviews

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Hawaiian Airlines

7.9

Good

2,317 reviews

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Sun Country Air

7.0

Good

374 reviews

Southwest

8.1

Very good

4,411 reviews

Reviews

1 / 20

10.0

Excellent

Arlene,May 2024

SAN - OAK

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

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 4 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 $118. Other airlines that can offer you cheap pricing are Southwest, from $227, and Delta, from $253. Users have found that Spirit Airlines is 62% 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 $57. Users have also found prices from $99 and $129 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, 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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Lansing

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Top 4 airlines flying from Oakland to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$130	Average$287	FlexibilityNo cancel fee	On-time65%
Alaska Airlines	Cheapest$138	Average$377	FlexibilityNo cancel fee	On-time75%
Delta	Cheapest$235	Average$360	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$263	Average$406	FlexibilityNo cancel fee	On-time63%

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$57+ 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 3/24. 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

The best prices from Oakland to Chicago are usually found in April or August, booked 89 days in advance, depart on a Friday or Saturday 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 febrero 20, 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 febrero 20, 2025.

Find flights from Oakland to Chicago within your budget

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 February.

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.

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 February 14, 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 febrero 20, 2025.

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 February 16, 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

Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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?

Traveling to a place near Oakland?

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 4 airlines flying from Oakland 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 febrero 20, 2025.