Cheap flights from Oakland to Chicago (OAK - CHI)

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The best prices from Oakland to Chicago are usually found in August or July, booked 53 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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

All the information you need to plan the best OAK to CHI flight in 2021: compare Oakland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
OAK - CHI
Price
$114 - $334
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

December

High demand for flights, 31% potential price rise

Cheapest in

August

Best time to find cheap flights, 51% potential price drop

Round-trip from

$114

From Oakland to Chicago (CHI)

One-way from

$66

One-way flight from Oakland to Chicago (CHI)

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 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 57% by booking at least 32 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 $363.

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

The best pricing can be found in the month of August. Prices to Chicago from Oakland, California average $287. You can even find prices in August for less than $287, as users have found deals to Chicago from as low as $118. 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%.

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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 18% on airfare.

Cheap flights from Oakland to Chicago in October, November 2021

The best prices found for OAK to CHI flights for October, November
9 Nov - 17 Nov
$64pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
2 Nov - 4 Nov
$65pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
27 Oct - 17 Nov
$67pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland

Oakland to Chicago 2021 flight deals

Cheap flights to Chicago from Oakland found for this year
7 Dec - 11 Dec
$63pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
9 Nov - 17 Nov
$64pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
2 Nov - 4 Nov
$65pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland

Last minute flights from Oakland to Chicago

Late deals on round-trip flights to Chicago from Oakland, departing today and this week
27 Oct - 17 Nov
$67pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
27 Oct - 2 Nov
$72pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
28 Oct - 3 Nov
$74pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland

One-way flights to Chicago from Oakland

The cheapest one-way flights from Oakland to Chicago
3:12 pm - 4:38 pm
Frontier
1 Stop
23h 26m
OAK - ORD
Frontier
$66
Kiwi.com
4:40 pm - 1:38 pm
Spirit Airlines
3 Stops
18h 58m
OAK - ORD
Spirit Airlines
$69
FareScan
8:43 am - 8:19 am
Multiple Airlines
1 Stop
21h 36m
OAK - ORD
Multiple Airlines
$70
Kiwi.com

Related info for your journey

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

Flight FAQs

From Oakland to Chicago

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 4 daily outbound flights to Chicago from 7 different airlines.

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

Some of our airline partners flying from Oakland to Chicago have new flexible policies in place due to COVID-19. Spirit Airlines, United Airlines, and Delta are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Spirit Airlines with this kind of flexibility.

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

Yes, there are multiple flights from Oakland, California to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $63, but on average you can expect to pay $76.

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

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

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

Cheapflights users have booked flights from Oakland, California to Chicago round-trip from $63. Users have found that Spirit Airlines is 72% cheaper than the other options available to this destination.

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

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

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 cheapest flights from Oakland, California to Chicago?

While on average a flight from Oakland, California to Chicago is generally $478, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Oakland - Chicago O'Hare Intl), you can expect to pay $63 for that flight.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

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

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

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.

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

Returning to Oakland from Chicago

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.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Oakland to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Oakland to Chicago.
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Oakland

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 5 airlines flying from Oakland to Chicago

The chart below displays the airlines Cheapflights users traveling from Oakland to Chicago 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
$123 $299 No cancel fee 75%
American Airlines
$138 $391 No cancel fee 71%
United Airlines
$138 $386 No cancel fee 69%
Spirit Airlines
$143 $298 No cancel fee 65%
Delta
$147 $525 No cancel fee N/A

Hourly flight availability from Oakland to Chicago

See what time of day planes typically take off from Oakland towards Chicago.
Morning 6 AM to noon 67% of OAK to CHI departures
Early morning Midnight to 6 AM 17% of OAK to CHI departures
Afternoon Noon to 6 PM 16% of OAK to CHI departures
Evening 6 PM to midnight 0% of OAK to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Oakland to Chicago
See how many times per day planes take to the skies headed from Oakland to Chicago.
Sunday
0 flights
Monday
6 daily flights
Tuesday
6 daily flights
Wednesday
6 daily flights
Thursday
6 daily flights
Friday
6 daily flights
Saturday
0 flights
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