Oakland San Francisco Bay Airport
Oakland, United StatesOAK / KOAK
Major airport · 61 direct destinations · 4 runways · longest runway 10,518 ft
68 °F · ClearSource: METAR observation via the NOAA Aviation Weather Center
Route
Oakland → Chicago
OAK
OaklandOakland San Francisco Bay Airport
OaklandOakland San Francisco Bay AirportMDWChicagoChicago Midway International Airport
ChicagoChicago Midway International Airport- Distance
- 1,840 mi
- Estimated flight time
- ~4h 10m
Chicago is currently 2 hours ahead of Oakland.
Observed nonstop
How often does this route fly?
Frequency
A couple of times a day
On average around 2 flights a day, observed from October 2025 to September 2026.
- 2
- flights per day
- 2
- busiest month · Mar
- 1
- quietest month · Oct
- 3 hr 35 min
- measured flight time
- 12 / 12
- months seen
Through the year
Per day, month by month
- 1Jan2026
- 1Feb
- 2Mar
- 2Apr
- 2May
- 2Jun
- 2Jul
- 2Aug
- 2Sep
- 1Oct2025
- 1Nov
- 1Dec
Airlines
Who flies it
Southwest Airlinesall year
Through the day
Departure times
Local time in Oakland. Most departures between 05:00 and 08:00.
- 00:00
- 01:00
- 02:00
- 03:00
- 04:00
- 05:00
- 06:00
- 07:00
- 08:00
- 09:00
- 10:00
- 11:00
- 12:00
- 13:00
- 14:00
- 15:00
- 16:00
- 17:00
- 18:00
- 19:00
- 20:00
- 21:00
- 22:00
- 23:00
Through the week
By weekday
- 1.8Mon
- 1.7Tue
- 1.8Wed
- 1.6Thu
- 1.7Fri
- 1.2Sat
- 1.5Sun
Fleet
Aircraft observed
- Boeing 737 MAX 8B38M52%
- Boeing 737-800B73828%
- Boeing 737-700B7379%
- Gulfstream VGLF51%
- Bombardier Challenger 350CL351%
All the numbers in a table
| Month | Per day | Seen | Airlines |
|---|---|---|---|
| January 2026 | 1 | 35 |
|
| February 2026 | 1 | 32 |
|
| March 2026 | 2 | 52 |
|
| April 2026 | 2 | 56 |
|
| May 2026 | 2 | 49 |
|
| June 2026 | 2 | 64 |
|
| July 2026 | 2 | 63 |
|
| August 2026 | 2 | 60 |
|
| September 2026 | 2 | 60 |
|
| October 2025 | 1 | 40 |
|
| November 2025 | 1 | 33 |
|
| December 2025 | 1 | 34 |
|
Airlines observed on this route
From observed callsign routes on OAK-MDW - not a booking guarantee.
About this route
- Domestic route: both airports are in the same country.
- The opposite direction has also been observed as a direct connection.
- Direct destinations observed from Oakland: 61.
- Direct destinations observed from Chicago: 108.
The airports on this route
Chicago Midway International Airport
Chicago, United StatesMDW / KMDW
Major airport · 108 direct destinations · 4 runways · longest runway 6,522 ft
52 °F · CloudySource: METAR observation via the NOAA Aviation Weather Center
Alternative airports for this journey
Same journey, a different airport nearby - with an observed direct connection.
SFO MDWSan Francisco International AirportSan Francisco is about 11 mi from Oakland.View route →OAK ORDChicago O'Hare International AirportChicago is about 16 mi from Chicago.View route →OAK GYYGary/Chicago International AirportGary is about 21 mi from Chicago.View route →SJC MDWMineta San Jose International AirportSan Jose is about 29 mi from Oakland.View route →
About the route from Oakland to Chicago
The observed direct connection between Oakland San Francisco Bay Airport (OAK) and Chicago Midway International Airport (MDW) covers approximately 1,840 mi. The estimated flight time is around 4h 10m. Southwest Airlines has been observed on this connection in the available route data.
Frequently asked questions about this route
- How far is Oakland from Chicago by air?
- The great-circle distance between Oakland San Francisco Bay Airport and Chicago Midway International Airport is approximately 1,840 mi.
- How long is the flight from Oakland to Chicago?
- Based on the distance, the estimated flight time is about 4h 10m. This is an estimate, not a schedule.
- Is there a direct connection from Oakland to Chicago?
- Yes, a direct connection between OAK and MDW has been observed in our route data.
- Which airlines have been observed on this route?
- In the available route data: Southwest Airlines.
- How often is there a flight from Oakland to Chicago?
- On average around 2 flights a day, measured over twelve months (October 2025 to September 2026) in the flight archive, with 578 observed flights. Mainly Southwest Airlines. That is an observation, not a timetable.
- What is the current time difference between Oakland and Chicago?
- Chicago is currently 2 hours ahead of Oakland.
Where this data comes from
The route data comes from the flight archive (ADS-B, adsb.lol): which connections actually flew over the last twelve full months and who flew them, combined with our own airport, runway, and airline datasets. It is reference data about observed routes - not a current timetable and no claim about bookability.
The frequency and aircraft on this page come from the flight archive (ADS-B, 12 months, October 2025 to September 2026), summarized per route per month. We do not see every flight, so it is a floor, not a count.
Route data updated on October 11, 2026.