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Cheap flights from Oakland International to Chicago (OAK - CHI)

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The best prices from Oakland International 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 International (OAK) to Chicago (CHI)

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 International to Chicago

One-way from

$76

One-way flight from Oakland International 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 International to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 21%.

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

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Oakland International to Chicago 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Oakland International in April are about $135 on average during April, but can be found for as low as $33.

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

It’s typically best to fly out from Oakland International to Chicago in the evening. Doing so could potentially save you 18% on the flight price compared to flying at noon, which is usually more expensive.

Cheap flights from Oakland International to Chicago in January, February 2021

The best prices found for OAK to CHI flights for January, February
22 Feb - 1 Mar
$75pp
OAK
Oakland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland
18 Feb - 19 Feb
$86pp
OAK
Oakland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland
15 Feb - 19 Feb
$98pp
OAK
Oakland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland

Oakland International to Chicago 2021 flight deals

Cheap flights to Chicago from Oakland International found for this year
22 Feb - 1 Mar
$75pp
OAK
Oakland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland
18 Feb - 19 Feb
$86pp
OAK
Oakland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland
15 Feb - 19 Feb
$98pp
OAK
Oakland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
OAK
Oakland

Non-stop flights to Chicago from Oakland International

Save time with Oakland International to Chicago direct flight deals
7 May - 15 May
$110pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
14 Apr - 30 Apr
$115pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
4 Jun - 7 Jun
$170pp
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 International to Chicago

Late deals on round-trip flights to Chicago from Oakland International, departing today and this week
23 Jan - 25 Jan
$135pp
OAK
Oakland
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OAK
Oakland
23 Jan - 24 Jan
$142pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
23 Jan - 26 Jan
$146pp
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 International

The cheapest one-way flights from Oakland International to Chicago
10:29 am - 7:24 pm
Frontier
1 Stop
6h 55m
OAK - ORD
Frontier
$76
CheapFlights
7:30 am - 5:21 pm
Multiple Airlines
3 Stops
31h 51m
OAK - ORD
Multiple Airlines
$88
Kiwi.com
1:40 pm - 11:50 am
Spirit Airlines
3 Stops
20h 10m
OAK - ORD
Spirit Airlines
$92
Gotogate

Related info for your journey

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

Flight FAQs

From Oakland International 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.

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

Yes, there are multiple flights from Oakland International to Chicago for under $100. The cheapest flight booked recently is on Multiple Airlines for just $75, but on average you can expect to pay $119.

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

Cheapflights has at least 5 direct flights from Oakland International to Chicago under $200. A good price for a nonstop flight from Oakland International to Chicago is less than $246.

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

There are currently 18+ open flights from Oakland International 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: Monday, 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 International to Chicago?

Spirit Airlines, Frontier, and Delta can get you from Oakland International to Chicago in just under 4h 11m. Your travel time can differ by up to 4h 43m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Oakland International to Chicago round-trip?

Our cheapest airline available from Oakland International to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $86 on this airline. An additional option worth looking into is Spirit Airlines, starting at $110. Frontier is priced at 62% lower than the current average price of a flight leaving 3 months from now.

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

One-way options have recently been found by users for as low as $42 on Spirit Airlines. Another option is Frontier, who have fights from $43.

Alternative routes for Oakland International to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Oakland International to Chicago
Flight duration
4h 23m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Oakland

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 5 airlines flying from Oakland International to Chicago

The chart below displays the airlines Cheapflights users traveling from Oakland International 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 International to Chicago

Early morning Midnight to 6 AM 50% of OAK to CHI departures
Afternoon Noon to 6 PM 50% of OAK to CHI departures
Morning 6 AM to noon 0% 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 International to Chicago
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
3 daily flights
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