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
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 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

One-way from

$57

One-way flight from Oakland to Chicago

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 to Chicago?

It’s generally more expensive to depart on a Monday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

To save on the cost of your flight from Oakland to Chicago, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

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

Flights from Oakland to Chicago lean towards being more expensive in December. Prices are generally better when you fly from Oakland to Chicago in April, with the cheapest ticket starting at $33.

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

One of the essential ways to save on airfare from Oakland 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 May, June 2021

The best prices found for OAK to CHI flights for May, June
20 May - 24 May
$100pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
9 Jun - 30 Jun
$114pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
9 Jun - 19 Jun
$115pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland

Oakland to Chicago 2021 flight deals

Cheap flights to Chicago from Oakland found for this year
20 May - 24 May
$100pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
20 Jul - 22 Jul
$111pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
9 Jun - 30 Jun
$114pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland

Non-stop flights to Chicago from Oakland

Save time with Oakland to Chicago direct flight deals
20 Jul - 22 Jul
$111pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
9 Jun - 30 Jun
$114pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
9 Jun - 19 Jun
$115pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-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
11 May - 25 May
$132pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
12 May - 18 May
$144pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
11 May - 15 May
$155pp
OAK
Oakland
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
OAK
Oakland

One-way flights to Chicago from Oakland

The cheapest one-way flights from Oakland to Chicago
7:00 pm - 1:05 am
Spirit Airlines
Nonstop
4h 05m
OAK - ORD
Spirit Airlines
$57
Spirit
7:00 pm - 1:00 am
Spirit Airlines
Nonstop
4h 00m
OAK - ORD
Spirit Airlines
$62
CheapOair
7:00 pm - 1:05 am
Spirit Airlines
Nonstop
4h 05m
OAK - ORD
Spirit Airlines
$68
JustFly

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

Are flight prices decreasing from Oakland to Chicago 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 Oakland and Chicago 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 Oakland to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Alaska Airlines and Delta are some airlines that have done so. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Oakland to Chicago. Policies will vary by airline.

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.

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 3 daily outbound flights to Chicago from 7 different airlines.

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

Yes, there are multiple flights from Oakland to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $100, but on average you can expect to pay $122.

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

Cheapflights has at least 20 direct flights from Oakland to Chicago under $200. A good price for a nonstop flight from Oakland to Chicago is less than $140.

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

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

What days are nonstop flights available from Oakland to Chicago?

Nonstop flights are available for this route on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

Is Oakland weather warmer or cooler than Chicago?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago are hotter than in Oakland.

How long is the flight from Oakland to Chicago?

For as low as $114, Spirit Airlines can have you in Chicago from Oakland in 4h. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

Flying on Spirit Airlines is currently your cheapest option to Chicago, with prices starting at $100. This flight start at 56% lower than the current average price 3 months from now.

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

The cheapest airline for a one-way flight from Oakland to Chicago is Spirit Airlines ($53).

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.
Flight duration
4h 20m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing Oakland

Airports servicing Chicago

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
Spirit Airlines
$143 $298 No cancel fee 65%
Alaska Airlines
$123 $299 No cancel fee 75%
United Airlines
$138 $386 No cancel fee 69%
American Airlines
$138 $391 No cancel fee 71%
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 85% of OAK to CHI departures
Early morning Midnight to 6 AM 8% of OAK to CHI departures
Afternoon Noon to 6 PM 7% 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
5 daily flights
Monday
5 daily flights
Tuesday
3 daily flights
Wednesday
3 daily flights
Thursday
5 daily flights
Friday
5 daily flights
Saturday
0 flights
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