San Diego International Airport
San Diego, United StatesSAN / KSAN
Major airport · 90 direct destinations · 1 runway · longest runway 9,400 ft
87 °F · Partly cloudySource: METAR observation via the NOAA Aviation Weather Center
Route
San Diego → Chicago
SAN
San DiegoSan Diego International Airport
San DiegoSan Diego International AirportMDWChicagoChicago Midway International Airport
ChicagoChicago Midway International Airport- Distance
- 1,725 mi
- Estimated flight time
- ~4h
Chicago is currently 2 hours ahead of San Diego.
Observed nonstop
How often does this route fly?
Frequency
A couple of times a day
On average around 3 flights a day, observed from October 2025 to September 2026.
- 3
- flights per day
- 4
- busiest month · Sep
- 2
- quietest month · Jan
- 3 hr 24 min
- measured flight time
- 12 / 12
- months seen
Through the year
Per day, month by month
- 2Jan2026
- 2Feb
- 3Mar
- 3Apr
- 3May
- 3.5Jun
- 3Jul
- 3Aug
- 4Sep
- 3Oct2025
- 3Nov
- 3Dec
Airlines
Who flies it
Southwest Airlinesall year
Through the day
Departure times
Local time in San Diego. Most departures between 06:00 and 09:00.
- 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
- 2.7Mon
- 3.3Tue
- 2.7Wed
- 2.7Thu
- 3.4Fri
- 3.3Sat
- 2.7Sun
Fleet
Aircraft observed
- Boeing 737 MAX 8B38M42%
- Boeing 737-700B73728%
- Boeing 737-800B73826%
- Bombardier Challenger 350CL351%
- Cessna Citation XC7500%
All the numbers in a table
| Month | Per day | Seen | Airlines |
|---|---|---|---|
| January 2026 | 2 | 66 |
|
| February 2026 | 2 | 63 |
|
| March 2026 | 3 | 91 |
|
| April 2026 | 3 | 97 |
|
| May 2026 | 3 | 94 |
|
| June 2026 | 3.5 | 108 |
|
| July 2026 | 3 | 100 |
|
| August 2026 | 3 | 98 |
|
| September 2026 | 4 | 107 |
|
| October 2025 | 3 | 90 |
|
| November 2025 | 3 | 79 |
|
| December 2025 | 3 | 78 |
|
Airlines observed on this route
From observed callsign routes on SAN-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 San Diego: 90.
- 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.
SAN ORDChicago O'Hare International AirportChicago is about 16 mi from Chicago.View route →SNA MDWJohn Wayne Orange County International AirportSanta Ana is about 76 mi from San Diego.View route →SAN MKEGeneral Mitchell International AirportMilwaukee is about 81 mi from Chicago.View route →PSP MDWPalm Springs International AirportPalm Springs is about 85 mi from San Diego.View route →
About the route from San Diego to Chicago
The observed direct connection between San Diego International Airport (SAN) and Chicago Midway International Airport (MDW) covers approximately 1,725 mi. The estimated flight time is around 4h. Southwest Airlines has been observed on this connection in the available route data.
Frequently asked questions about this route
- How far is San Diego from Chicago by air?
- The great-circle distance between San Diego International Airport and Chicago Midway International Airport is approximately 1,725 mi.
- How long is the flight from San Diego to Chicago?
- Based on the distance, the estimated flight time is about 4h. This is an estimate, not a schedule.
- Is there a direct connection from San Diego to Chicago?
- Yes, a direct connection between SAN 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 San Diego to Chicago?
- On average around 3 flights a day, measured over twelve months (October 2025 to September 2026) in the flight archive, with 1,071 observed flights. Mainly Southwest Airlines. That is an observation, not a timetable.
- What is the current time difference between San Diego and Chicago?
- Chicago is currently 2 hours ahead of San Diego.
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.