Cheap flights from Oakland (OAK) to Chicago (CHI) from $68
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 5/28. 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.
The best prices from Oakland to Chicago are usually found in October or January, booked 18 days in advance, depart on a Monday 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 April 27, 2024.
Popular in | June |
|---|---|
Cheapest in | October |
Round-trip from | $222 |
One-way from | $91 |
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 54% by booking at least 36 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 $358.
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 $346. You can even find prices in September for less than $346, as users have found deals to Chicago from as low as $105. The month of June 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 21%.
When is the cheapest time to fly from Oakland, California to Chicago (OAK - 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 at noon could potentially save you up to 20% on airfare.
Cheap Sun Country Air flights from Oakland to Chicago
Explore cheap flight options specifically provided by Sun Country Air for the route between Oakland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 27, 2024.
Check out some of the cheapest Sun Country Air flights we've come across from Oakland to Chicago. It's recommended that users confirm their flight details before booking.
Cheap Spirit Airlines flights from Oakland to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between Oakland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 27, 2024.
Take a gander at the lowest prices we've found on Spirit Airlines flights from Oakland to Chicago. Deals are refreshing constantly so come back soon for more options.
Cheap Oakland to Chicago flights in April & May 2024
Find cheap flight options from Oakland to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,991,349 searches. Prices were last updated on April 27, 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.
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 2,991,349 searches. Data last updated April 27, 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.
Non-stop flights to Chicago from Oakland
Discover non-stop flight options from Oakland to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 27, 2024.
For a quicker trip, book one of these direct flights from Oakland to Chicago. Select from other flights from Oakland to Chicago by using the search form above.
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 2,991,349 searches. Data last updated April 27, 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.
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 2,991,349 searches. Data last updated April 27, 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.
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 2,991,349 searches. Data last updated April 27, 2024.
Fly from
Fly to
Budget
$123 - $385
Route
Depart
Return
Price
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Tue 5/7
1 stop8h 22m
Chicago O'Hare Intl
Sat 5/11
1 stop8h 50m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Wed 5/15
1 stop14h 25m
Chicago O'Hare Intl
Tue 5/21
1 stop24h 48m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Tue 5/7
1 stop16h 41m
Chicago O'Hare Intl
Tue 5/14
3 stops29h 00m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Tue 5/7
1 stop16h 41m
Chicago O'Hare Intl
Tue 5/14
2 stops27h 52m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Sat 5/11
2 stops17h 12m
Chicago O'Hare Intl
Tue 5/14
2 stops18h 02m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Mon 6/10
2 stops16h 41m
Chicago O'Hare Intl
Wed 6/12
1 stop28h 48m
OaklandChicago O'Hare Intl
OAK - ORD
OAKORD
Oakland
Sun 6/16
1 stop17h 07m
Chicago O'Hare Intl
Mon 7/8
1 stop11h 24m
OaklandChicago Midway
OAK - MDW
OAKMDW
Oakland
Fri 8/2
1 stop8h 19m
Chicago Midway
Tue 8/6
1 stop7h 50m
OaklandChicago Midway
OAK - MDW
OAKMDW
Oakland
Mon 5/20
1 stop7h 00m
Chicago Midway
Wed 5/22
1 stop6h 35m
When is the best time to 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 January 28, 2024.
The best time to book flights from Oakland, California to Chicago is 18 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.
When is the cheapest time 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 April 21, 2024.
Average price of flights to Chicago by month
Plan your trip from Oakland to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Oakland to Chicago is currently $77 while a round-trip flight costs $205. Price data was last updated on April 21, 2024.
Currently, February 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 June is currently the most expensive (average of $356). 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.
January
$248
February
$245
March
$280
April
$273
May
$282
June
$356
July
$336
August
$276
September
$258
October
$248
November
$270
December
$248
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 |
|---|
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 April 27, 2024.
Peruse reviews from past customers who have flown with Sun Country Air, Spirit 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.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Food
Crew
Boarding
Comfort
Overall
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
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.
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Alternative routes for Oakland to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
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 2,991,349 searches. Data last updated April 27, 2024.
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.
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 April 27, 2024.
| 59%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 12%of flight departures | Morning6 am to noon |
| 29%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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 April 27, 2024.
| Sunday | 4daily flights |
|---|---|
| Monday | 10daily flights |
| Tuesday | 7daily flights |
| Wednesday | 7daily flights |
| Thursday | 10daily flights |
| Friday | 10daily flights |
| Saturday | 4daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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How does Cheapflights help users find flights from Oakland to Chicago?
Cheapflights makes it easy to find Oakland to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Oakland.
Can Cheapflights find flights from Oakland to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Oakland to Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Oakland to Chicago become cheaper?
Not ready to book yet? You can track prices for flights from Oakland to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.