Good to know - Cheap tickets Oakland — Chicago
| Cheapest flight found | $67 |
|---|---|
| Minimal flight time | 4h 0m |
| Flight distance | 2972 km |
| Most popular airline | Southwest Airlines |
Airfare Oakland – Chicago by month
Here you can find out in what months how much a ticket Oakland – Chicago costs to buy cheap plane tickets.
| Month | One-way | Round-trip |
|---|---|---|
| January 2026 | ||
| December 2025 | ||
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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 Oakland — Chicago
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:05 | 11:15 | mon, thu, fri | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 12:00 | tue, wed | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 05:55 | 12:05 | mon, thu, fri | WN585 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 12:15 | sat, sun | WN189 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 12:25 | sat | WN585 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 12:30 | sun | WN585 | Southwest Airlines | 4h 10m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 06:35 | 12:40 | sat | WN346 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 07:40 | 13:45 | fri | WN585 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 12:05 | 18:10 | tue, wed | WN585 | Southwest Airlines | 4h 5m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
| 15:10 | 21:10 | sun | WN3105 | Southwest Airlines | 4h 0m | Metropolitan Oakland International Airport — Chicago Midway International Airport | Select dates |
Popular airlines flying Oakland — Chicago
Flight Oakland – Chicago is served by 16 airlines. 1 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Sales of tickets from Oakland to Chicago in the last 48 hours
Dynamics airfare Oakland — Chicago 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 Oakland — Chicago
The graph shows that booking flights Oakland — Chicago is best planned for July and flights Oakland — Chicago — Oakland in the month of May.
Flights Oakland — Chicago
The selection of cheap flights Oakland — Chicago
Here you can find and purchase the cheapest flights Oakland — Chicago from $67 and Oakland — Chicago — Oakland from $90.
The price of the flight Oakland — Chicago (United States) — Oakland from $90 (round-trip).
The average price of the flight Oakland — Chicago (United States) — Oakland $335 (round-trip).
- Departure city: Oakland
- IATA code of the city of origin: OAK
- Departure airports: Metropolitan Oakland International Airport, Convention Center Heliport
- Departure country: United States
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination 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
- Destination country: United States
Low cost flights Oakland — Chicago (OAK — CHI)
The distance between Oakland and Chicago 1847 miles (or 2972 kilometres).
The time difference between Oakland and Chicago is 2 h.
Minimal flight time from Oakland to Chicago 4h 0m.
LowCostClub always do a comparison of airfares Oakland — Chicago with several airlines (include Southwest Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Oakland — Chicago. Last week, for instance, the cheapest round-trip prices stood at $90 while the cheapest one-way price that was available within the last week cost $67
Routes from nearby cities to Chicago
A flight from a neighbouring city can help you save money on plane tickets.
Most often, departures to Chicago are from San Francisco, this is the cheapest flight from $46. The nearest airports from Oakland with a flight to Chicago are located in Reno.
Popular International routes from Oakland
Popular routes from Chicago
If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:
Popular domestic routes from Oakland
FAQ about Oakland — Chicago
Are there any direct flights Oakland — Chicago?
Yes, they do: WN189, WN585, WN346, WN3105
Can we fly from Oakland to Chicago?
Yes, you can fly from Oakland to Chicago. Oakland has 2 airports (Metropolitan Oakland International Airport, Convention Center Heliport) for flights. Southwest Airlines departs from Oakland on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Advanced Air, Alaska SkyWest, Allegiant Air, Breeze Airways, Contour Aviation, Delta Air Lines, Everts Air Alaska, FedEx, Jet Linx Aviation, NetJets, SkyWest Charter, Spirit Airlines, Sun Country Airlines, UPS, Viva, Volaris.
How long does it take to fly from Oakland to Chicago?
A direct flight lasts an average of 4h 0m, during which time the aircraft covers a distance of 2972 km.
How much do flights Oakland — Chicago cost?
The price of flights Oakland — Chicago starts from $67.
What days does the plane fly Oakland — Chicago?
Planes fly Oakland — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Oakland and Chicago?
In Oakland — Metropolitan Oakland International Airport, Convention Center Heliport. 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.
What flights are currently flying from Oakland to Chicago?
The following flights fly between Oakland and Chicago: WN189, WN189, WN585, WN189, WN585, WN585, WN346, WN585, WN585, WN3105
What month is the cheapest to fly from Oakland to Chicago?
High season is considered to be January and the cheapest month is July. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Oakland — Chicago flight deals.
Which airlines direct fly from Oakland to Chicago?
Only one airline operates a direct flight Oakland — Chicago: Southwest Airlines.
Which airlines fly from Oakland to Chicago?
All the following airlines flights Oakland — Chicago: Advanced Air, Alaska SkyWest, Allegiant Air, Breeze Airways, Contour Aviation, Delta Air Lines, Everts Air Alaska, FedEx, Jet Linx Aviation, NetJets, SkyWest Charter, Southwest Airlines, Spirit Airlines, Sun Country Airlines, UPS, Viva, Volaris.