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Cheap flights from Chicago to Oakland (CHI - OAK)

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The best prices from Chicago to Oakland are usually found in August or July, booked 26 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

How to find the cheapest flight from
Chicago (CHI) to Oakland (OAK)

CHI - OAK
Price
$114 - $332
OAK
Temperature
59 - 77 °F
OAK
Rainfall
0 - 4.7 inches

Popular in

December

High demand for flights, 34% potential price rise

Cheapest in

August

Best time to find cheap flights, 48% potential price drop

Round-trip from

$114

From Chicago to Oakland

One-way from

$44

One-way flight from Chicago to Oakland

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Oakland?

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 36% on the overall cost on flights from Chicago to Oakland.

How far in advance should I book a flight from Chicago to Oakland?

To save on the cost of your flight from Chicago to Oakland, book at least 29 days before your planned departure. Booking around this time can save you about 70% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $362 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $543.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Oakland. Flights to Oakland from Chicago in August are about $299 on average during August, but can be found for as low as $82.

When is the cheapest time to fly from Chicago to Oakland (CHI - OAK)?

It’s typically best to fly out from Chicago to Oakland in the evening. Doing so could potentially save you 35% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Chicago to Oakland in December, January 2021

The best prices found for CHI to OAK flights for December, January
18 Dec - 20 Dec
$89pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
16 Dec - 19 Dec
$90pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Dec - 12 Jan
$104pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Oakland 2021 flight deals

Cheap flights to Oakland from Chicago found for this year
18 Dec - 20 Dec
$89pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
16 Dec - 19 Dec
$90pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Dec - 12 Jan
$104pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Oakland from Chicago

Save time with Chicago to Oakland direct flight deals
19 May - 24 May
$131pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
19 May - 24 May
$133pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
21 Apr - 25 Apr
$476pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Oakland

Late deals on round-trip flights to Oakland from Chicago, departing today and this week
9 Dec - 15 Dec
$105pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
8 Dec - 10 Dec
$115pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 17 Dec
$116pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Oakland from Chicago

The cheapest one-way flights from Chicago to Oakland
4:11 am - 12:41 pm
Spirit Airlines
1 Stop
10h 30m
ORD - OAK
Spirit Airlines
$44
mytrip.com
1:10 am - 11:01 am
Multiple Airlines
1 Stop
11h 51m
ORD - OAK
Multiple Airlines
$50
Gotogate
1:00 am - 10:24 am
Spirit Airlines
1 Stop
11h 24m
ORD - OAK
Spirit Airlines
$52
FlightNetwork

Related info for your journey

Useful info, stats and facts about Chicago to Oakland flights.

Flight FAQs

From Chicago to Oakland

Are flight prices decreasing from Chicago to Oakland due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Oakland for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Oakland to control the spread of COVID-19?

Alaska Airlines and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Some of the new policies that have been implemented to accommodate travelers flying from Chicago to Oakland are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Chicago to Oakland have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Oakland that may be offering flexible cancellation policies are Spirit Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Oakland for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Oakland for under $100. The cheapest flight booked recently is on Spirit Airlines for just $89, but on average you can expect to pay $118.

Are there nonstop flights from Chicago to Oakland for under $200 on Cheapflights?

Cheapflights has at least 3 direct flights from Chicago to Oakland under $200. A good price for a nonstop flight from Chicago to Oakland is less than $246.

Are there last-minute flights available from Chicago to Oakland for under $200?

There are currently 20+ open flights from Chicago to Oakland within the next 7 days for less than $200.

Is Chicago weather warmer or cooler than Oakland?

You can imagine temperatures to be in the 84 °F range in July. The weather in Oakland is generally colder than Chicago's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long is the flight from Chicago to Oakland?

Airlines like Spirit Airlines and Delta fly from Chicago to Oakland in about 4h 35m. The time it takes to get you to your destination can typically vary by up to 5h 19m. This flight may include one or multiple stops.

What is the cheapest airline to fly from Chicago to Oakland round-trip?

Flying on Spirit Airlines is currently your cheapest option to Oakland, with prices starting at $89. Spirit Airlines is priced at 59% lower than the current average price of a flight leaving 3 months from now.

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

One-way options have recently been found by users for as low as $44 on Spirit Airlines.

Alternative routes for Chicago to Oakland

Destination information for Oakland

Things to know before you go. Useful info for your trip from Chicago to Oakland
Average temperature for December in Oakland
59.0 °F
Avg rainfall for December in Oakland
4.7 ″

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Airports servicing Oakland

Top 5 airlines from Chicago to Oakland

The chart below displays the airlines Cheapflights users traveling from Chicago to Oakland choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$136 $255 No cancel fee 65%
United Airlines
$147 $279 No cancel fee 69%
American Airlines
$138 $364 No cancel fee 71%
Delta
$167 $480 No cancel fee N/A
Alaska Airlines
$128 $531 No cancel fee 75%

Hourly flight availability from Chicago to Oakland

Afternoon Noon to 6 PM 50% of CHI to OAK departures
Morning 6 AM to noon 33% of CHI to OAK departures
Early morning Midnight to 6 AM 17% of CHI to OAK departures
Evening 6 PM to midnight 0% of CHI to OAK departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Oakland
Sunday
3 daily flights
Monday
3 daily flights
Tuesday
3 daily flights
Wednesday
3 daily flights
Thursday
3 daily flights
Friday
3 daily flights
Saturday
0 flights
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