Flights from Oakland to Chicago from $67

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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 $67. 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.

Sun

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 Oakland
Cheap flights to Chicago
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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 $67 – the departure date for this flight is 22 May 2025.

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10.06.2025 Tuesday

from $102 Trip.com

Economy Found 2025-05-13

Nonstop 4 hours 20 min

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*Prices include: baggage, hand luggage, airline fees and charges.

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 $179, the flight dates are: there on 21 May 2025 year and back on 07 June 2025 year.

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Spirit Airlines NK 2330 Night flight

Departure 22.05.25 04:09, Th

1 Stopover Trip 2 days

Return 24.05.25 13:00, Sa

Find Flights from $328

Alaska Airlines AS 1247 Evening flight

Departure 20.05.25 21:31, Tu

1 Stopover Trip 2 days

Return 23.05.25 02:09, Fr

Find Flights from $468

*Prices include: baggage, hand luggage, airline fees and charges.

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 2 flights every day, from 4hours 10min. Local departure and arrival times are indicated.

05:05 → 11:15

Southwest Airlines WN189

OAK → MDW

Mo - - Th Fr - -

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05:50 → 12:00

Southwest Airlines WN189

OAK → MDW

- Tu We - - - -

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05:55 → 12:05

Southwest Airlines WN189

OAK → MDW

- - - - - - Su

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06:05 → 12:15

Southwest Airlines WN189

OAK → MDW

- - - - - Sa -

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06:40 → 15:45

Southwest Airlines WN1252

OAK → MDW

Mo - - Th Fr - -

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08:05 → 17:45

Southwest Airlines WN1365

OAK → MDW

- - - - - - Su

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09:10 → 17:20

Southwest Airlines WN2932

OAK → MDW

- Tu We - - - -

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10:00 → 18:50

Southwest Airlines WN2891

OAK → MDW

- - - - - Sa -

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*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 .

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.

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All flights from Oakland

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 $33 20 May 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 $48 20 May 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 $36 22 May 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 $36 22 May 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 $83 20 May 2025

All flights to Chicago

Tips for buying a ticket

Oakland – Chicago – Oakland round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Oakland to Chicago — Chicago city

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