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)

All the information you need to plan the best CHI to OAK flight in 2021: compare Chicago to Oakland flight prices with the expected peak season, weather and rainfall in Oakland.
CHI - OAK
Price
$114 - $332
OAK
Temperature
51.8 - 66.2 °F
OAK
Precipitation
0 - 4.8 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 All airports (CHI) to Oakland

One-way from

$59

One-way flight from Chicago All airports (CHI) 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, California?

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 39% on your flight compared to booking on days when demand is much higher.

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

To save up to 60% on this flight, we recommend booking at least 32 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Oakland, California from $362 1-2 weeks out and tickets from $460 for flights departing within the next 72 hours.

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

Our data shows that August tends to be the cheapest month to fly to Oakland, California from Chicago. Users have commonly found prices around $272 for the month, but tickets can be as low as $143. Due to multiple factors, prepare for potentially higher prices in December.

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

It’s typically best to fly out from Chicago to Oakland, California in the evening. Doing so could potentially save you 37% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Chicago to Oakland in September, October 2021

The best prices found for CHI to OAK flights for September, October
25 Oct - 2 Nov
$64pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Oct - 26 Oct
$65pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
22 Oct - 25 Oct
$67pp
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
25 Oct - 2 Nov
$64pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Oct - 26 Oct
$65pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
22 Oct - 25 Oct
$67pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 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
5 Oct - 9 Oct
$70pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
6 Oct - 13 Oct
$77pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
2 Oct - 4 Oct
$79pp
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
12:29 pm - 4:52 am
Multiple Airlines
1 Stop
18h 23m
MDW - OAK
Multiple Airlines
$59
Kiwi.com
5:45 pm - 7:58 am
Frontier
1 Stop
16h 13m
ORD - OAK
Frontier
$68
Kiwi.com
9:26 am - 3:28 am
Spirit Airlines
3 Stops
20h 02m
ORD - OAK
Spirit Airlines
$71
FareScan

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Oakland</span> flights.

Flight FAQs

From Chicago to Oakland

What airport do you fly into for flights to Oakland from Chicago?

Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Oakland from Chicago. Booking flights from Chicago to Oakland (OAK) should be relatively easy as there are 3 daily inbound flights from Chicago from 6 different airlines.

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 United Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Are flight prices decreasing from Chicago to Oakland, California 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, California 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.

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

Yes, there are multiple flights from Chicago to Oakland, California for under $100. The cheapest flight booked recently is on Spirit Airlines for just $64, but on average you can expect to pay $80.

Are there last-minute flights available from Chicago to Oakland, California for under $100?

There are currently 20+ open flights from Chicago to Oakland, California within the next 7 days for less than $100.

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

Our cheapest airline available from Chicago to Oakland, California is Spirit Airlines. Our recent data shows that you can find tickets from as low as $64 on this airline. This flight start at 70% lower than the current average price 3 months from now.

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

The most popular airlines flying from Chicago to Oakland, California are American Airlines, Alaska Airlines and Delta. Something to consider prior to booking your flight.

What are the cheapest flights from Chicago to Oakland, California?

The cheapest flight price from Chicago to Oakland, California is $62. On average you can expect to pay $369. The most popular route, (Chicago O'Hare Intl - Oakland), can usually be booked for $64.

COVID Restrictions

View COVID Travel Restrictions for Oakland, CA

Do I need a COVID test to fly to Oakland from Chicago?

Information is based on travel restrictions for travel to Oakland within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Oakland.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Oakland.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Oakland.

Do I need a test to fly back to Chicago from Oakland?

Returning to Chicago from Oakland

COVID-19 testing requirements
Visitors from Oakland must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Oakland are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Oakland, CA

Alternative routes for Chicago to Oakland

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Oakland

Things to know before you go - useful duration and weather info for your trip from Chicago to Oakland.
Average temperature for September in Oakland
77.0 °F
Avg rainfall for September in Oakland
0.1 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Oakland

Top 5 airlines flying 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
Alaska Airlines
$128 $531 No cancel fee 75%
Spirit Airlines
$136 $255 No cancel fee 65%
American Airlines
$138 $364 No cancel fee 71%
United Airlines
$147 $279 No cancel fee 69%
Delta
$167 $480 No cancel fee N/A

Hourly flight availability from Chicago to Oakland

See what time of day planes typically take off from Chicago towards Oakland.
Morning 6 AM to noon 69% of CHI to OAK departures
Evening 6 PM to midnight 17% of CHI to OAK departures
Afternoon Noon to 6 PM 13% of CHI to OAK departures
Early morning Midnight to 6 AM 1% of CHI to OAK departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Oakland
See how many times per day planes take to the skies headed from Chicago to Oakland.
Sunday
5 daily flights
Monday
5 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
5 daily flights
Friday
5 daily flights
Saturday
6 daily flights
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