Flights from Oakland to Chicago from $72
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Airfare Deals Oakland to Chicago
On HolidayPrice.com you will find 0 direct and 0 connecting flights from Oakland to Chicago at a price of from $72. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out OAK - CHI flight schedule to find best flight time, convenient departure and arrival airports.
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The cost of airline tickets from Oakland to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.
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Cheap flights from OaklandCheap flights to Chicago
Airline tickets to United States
One way flight from Oakland to Chicago
Below are the prices of tickets for direct one-way flights from Oakland to Chicago. The cheapest flight from Oakland to Chicago starts from $72 – the departure date for this flight is 30 December 2025.
30.12.2025
Tuesday
from $71
Kupi.com
Economy
Found 2025-10-30
1 Stopover
30 hours 5 min
Find Flights
02.12.2025
Tuesday
from $103
Vayama
Economy
Found 2025-11-02
1 Stopover
21 hours 32 min
Find Flights
Round trip from Oakland to Chicago
You can buy a round-trip ticket from Oakland to Chicago (United States) and back using the table below. The best offer starts from $322, the flight dates are: there on 06 November 2025 year and back on 06 November 2025 year.
Alaska Airlines AS 470
Night flight
Departure
14.03.26
01:35, Sa
1 Stopover
Trip 7 days
Return
21.03.26
02:05, Sa
Alaska Airlines AS 1359
Evening flight
Departure
08.11.25
22:49, Sa
2 Stopovers
Trip 3 days
Return
11.11.25
19:48, Tu
Alaska Airlines AS 2203
Evening flight
Departure
11.11.25
19:05, Tu
1 Stopover
Trip 4 days
Return
15.11.25
21:25, Sa
Not found promotions and sales.
Flight Schedule Oakland to Chicago 2025
The current flight schedule for the route from Oakland to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.
More than 1 flights every day, from 4hours 5min. Local departure and arrival times are indicated.
*Schedule is indicated only for direct scheduled flights and low-cost airlines.
Flight Information
Flying to Chicago from Oakland takes 04:29 minutes (excluding transfers). The distance between Oakland and Chicago is 1842 miles (2966 kilometers). Planes depart from Oakland between and . The fastest flight from the company with flight number . Flies for just minutes with departure from and arrival in .
Average flight time
04:29 min
Distance
1842 mi
The earliest flight
The latest flight
The fastest flight
Airlines
Direct flight
There are 0 airlines that fly directly from Oakland to Chicago. The most popular company carrying out non-stop flights is .
*Flight number
Flights with Transfers
Flights with transfers from Oakland to Chicago can be bought from 0 airlines:
*Transit cities
Airports
Airports serving the air communication between Oakland and Chicago. You can fly to Chicago from Oakland airports. Planes arrive at airport in Chicago.
Oakland airports:
Chicago airports:
*Distance from the airport to the city center
Aircraft
You can fly from Oakland to Chicago on board of airlines that utilize aircraft models.
Connecting cities
The list of cities on transfer flights to Chicago from Oakland. The best options are to fly through: .
Cheap airline tickets from Oakland to United States
Here is a list of flights from Oakland to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.
No directions were found for the specified parameters!Flights from United States to Chicago
Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.
New York - Chicago UA 761
United Airlines Boeing 737-800
13:00
LaGuardia
in a way 2 hours 0 min
Direct
15:00
O'Hare
Flights
from $27 15 November 2025
from $27 15 November 2025
Los Angeles - Chicago UA 910
United Airlines Boeing 737-800
10:23
Los Angeles
in a way 3 hours 37 min
Direct
14:00
O'Hare
Flights
from $50 15 November 2025
from $50 15 November 2025
Miami - Chicago AA 2796
American Airlines Boeing 767-300
17:05
Miami
in a way 2 hours 55 min
Direct
20:00
O'Hare
Flights
from $46 26 November 2025
from $46 26 November 2025
Miami - Chicago WN 1626
Southwest Airlines Boeing 737
13:35
Fort Lauderdale Executive Airport
in a way 3 hours 0 min
Direct
16:35
Chicago Midway
Flights
from $46 26 November 2025
from $46 26 November 2025
San Francisco - Chicago UA 1800
United Airlines Airbus A319
04:15
San Francisco
in a way 3 hours 45 min
Direct
08:00
O'Hare
Flights
from $64 12 January 2026
from $64 12 January 2026
Tips for buying a ticket
Oakland – Chicago – Oakland round-trip route are always cheaper than tickets purchased there and back separately.
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