Cheap flights Chicago — Oakland (CHI — OAK)

Good to know - Cheap tickets Chicago — Oakland

Minimal flight time 4h 1m
Flight distance 2972 km
Most popular airline UPS
Round-trip from $76

Airfare Chicago – Oakland by month

Here you can find out in what months how much a ticket Chicago – Oakland costs to buy cheap plane tickets.

Month One-way Round-trip
July 2026
June 2026
May 2026
April 2026
March 2026
February 2026
January 2026
December 2025
November 2025
October 2025
September 2025
August 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Chicago — Oakland

Departure Arrival Flight days Flight Airlines Flight time Airports
02:25 04:27 tue, wed, thu, fri 5X948 UPS 4h 2m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
02:25 04:32 tue 5X948 UPS 4h 7m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
02:25 04:26 fri 5X948 UPS 4h 1m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
09:55 12:40 sun WN2484 Southwest Airlines 4h 45m Chicago Midway International Airport — Metropolitan Oakland International Airport Select dates
10:00 12:45 tue, wed WN2484 Southwest Airlines 4h 45m Chicago Midway International Airport — Metropolitan Oakland International Airport Select dates
10:05 12:50 mon, thu, fri, sat WN2484 Southwest Airlines 4h 45m Chicago Midway International Airport — Metropolitan Oakland International Airport Select dates
11:10 14:05 tue, wed WN1371 Southwest Airlines 4h 55m Chicago Midway International Airport — Metropolitan Oakland International Airport Select dates
15:10 17:20 tue, wed, thu 5X2956 UPS 4h 10m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
15:10 17:17 mon 5X2956 UPS 4h 7m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
15:10 17:25 tue 5X2956 UPS 4h 15m Chicago Rockford International Airport — Metropolitan Oakland International Airport Select dates
All routes

Popular airlines flying Chicago — Oakland

Flight Chicago – Oakland is served by 13 airlines.  2 airlines operate direct flights.


Airlines with direct flights


Other airlines flying with transfers

Dynamics airfare Chicago — Oakland by month for the last year

according to LowCost.Club for the last year

The airfare depends on the departure date. Our chart shows the low season prices on route Chicago — Oakland

The graph shows that booking flights Chicago — Oakland is best planned for March and flights Chicago — Oakland — Chicago in the month of May.

Flights Chicago — Oakland

The selection of cheap flights Chicago — Oakland

The price of the flight Chicago — Oakland (United States) — Chicago from $76 (round-trip).

The average price of the flight Chicago — Oakland (United States) — Chicago $371 (round-trip).

Low cost flights Chicago — Oakland (CHI — OAK)

The distance between Chicago and Oakland 1847 miles (or 2972 kilometres).

The time difference between Chicago and Oakland is 2 h.

Minimal flight time from Chicago to Oakland 4h 1m.

Routes from nearby cities to Oakland

A flight from a neighbouring city can help you save money on plane tickets.

The closest airports to Chicago with a flight to Oakland are in Milwaukee.

Popular International routes from Chicago

Popular routes from Oakland

If you are going to fly from Oakland, then study the popular flights. The most popular flights from Oakland:

Popular domestic routes from Chicago

FAQ about Chicago — Oakland

Yes, they do: 5X948, WN2484, WN1371, 5X2956, 5X5956, 5X5942, WN470, WN1394

Yes, you can fly from Chicago to Oakland. Chicago has 8 airports (Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport) for flights. UPS, Southwest Airlines depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, Alaska Airlines, Allegiant Air, Contour Aviation, Delta Connection, FedEx, GlobalX, Jet Linx Aviation, NetJets, Phoenix Air, SkyWest Charter, Viva, Volaris.

A direct flight lasts an average of 4h 1m, during which time the aircraft covers a distance of 2972 km.

The price of flights Chicago — Oakland starts from $76.

Planes fly Chicago — Oakland 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport. In Oakland — Metropolitan Oakland International Airport, Convention Center Heliport.

The following flights fly between Chicago and Oakland: 5X948, 5X948, 5X948, WN2484, WN2484, WN2484, WN1371, 5X2956, 5X2956, 5X2956, 5X2956, 5X5956, 5X5942, WN470, WN1394, WN1394, WN1394

High season is considered to be October and the cheapest month is March. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — Oakland flight deals.

The following airlines have direct flights Chicago — Oakland: UPS, Southwest Airlines.

All the following airlines flights Chicago — Oakland: Air Canada, Alaska Airlines, Allegiant Air, Contour Aviation, Delta Connection, FedEx, GlobalX, Jet Linx Aviation, NetJets, Phoenix Air, SkyWest Charter, Southwest Airlines, UPS, Viva, Volaris.

Low price calendar