Cheap flights Chicago — San Diego (CHI — SAN)

Good to know - Cheap tickets Chicago — San Diego

Cheapest flight found $44
Minimal flight time 4h 10m
Flight distance 2787 km
Most popular airline United Airlines

Airfare Chicago – San Diego by month

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

Month One-way Round-trip
October 2025
September 2025
August 2025
July 2025
June 2025
May 2025
April 2025
March 2025
February 2025
January 2025
December 2024
November 2024

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 — San Diego

Departure Arrival Flight days Flight Airlines Flight time Airports
07:11 09:34 daily UA264 United Airlines 4h 23m O'Hare International Airport — San Diego International Airport Select dates
07:14 09:28 daily AA2343 American Airlines 4h 14m O'Hare International Airport — San Diego International Airport Select dates
07:25 09:40 sat WN2014 Southwest Airlines 4h 15m Chicago Midway International Airport — San Diego International Airport Select dates
07:35 09:50 tue, wed WN2014 Southwest Airlines 4h 15m Chicago Midway International Airport — San Diego International Airport Select dates
07:40 09:55 mon, thu, fri WN2014 Southwest Airlines 4h 15m Chicago Midway International Airport — San Diego International Airport Select dates
08:05 10:25 mon, thu, fri, sat WN3175 Southwest Airlines 4h 20m Chicago Midway International Airport — San Diego International Airport Select dates
08:10 10:25 sun WN3851 Southwest Airlines 4h 15m Chicago Midway International Airport — San Diego International Airport Select dates
08:20 10:40 tue, wed WN3175 Southwest Airlines 4h 20m Chicago Midway International Airport — San Diego International Airport Select dates
09:05 11:33 daily UA660 United Airlines 4h 28m O'Hare International Airport — San Diego International Airport Select dates
10:05 12:22 daily AA2131 American Airlines 4h 17m O'Hare International Airport — San Diego International Airport Select dates
All routes

Sales of tickets from Chicago to San Diego in the last 48 hours

2025-08-03 one-way

Dynamics airfare Chicago — San Diego 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 — San Diego

The graph shows that booking flights Chicago — San Diego is best planned for October and flights Chicago — San Diego — Chicago in the month of September.

Flights Chicago — San Diego

The selection of cheap flights Chicago — San Diego

Here you can find and purchase the cheapest flights Chicago — San Diego from $44 and Chicago — San Diego — Chicago from $86.

The price of the flight Chicago — San Diego (United States) — Chicago from $86 (round-trip).

The average price of the flight Chicago — San Diego (United States) — Chicago $408 (round-trip).

Low cost flights Chicago — San Diego (CHI — SAN)

The distance between Chicago and San Diego 1732 miles (or 2787 kilometres).

The time difference between Chicago and San Diego is 2 h.

Minimal flight time from Chicago to San Diego 4h 10m.

LowCostClub always do a comparison of airfares Chicago — San Diego with several airlines (include United Airlines, American Airlines, Southwest Airlines). They will always give you all available options so you can find the cheapest flight to San Diego. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — San Diego. Last week, for instance, the cheapest round-trip prices stood at $86 while the cheapest one-way price that was available within the last week cost $44

Routes from nearby cities to San Diego

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

The most frequent flight to San Diego is from Milwaukee. The cheapest airfare can be purchased with a flight from Madison from $57. The nearest airports from Chicago with a flight to San Diego are in Peoria.

Popular International routes from Chicago

Popular routes from San Diego

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

Popular domestic routes from Chicago

FAQ about Chicago — San Diego

Yes, they do: UA264, AA2343, WN2014, WN3175, WN3851, UA660, AA2131, UA2294, AA2309, F91855, WN2365, UA2683, UA2417, AA1543, WN3466, UA8124, WN1275, AA1861

Yes, you can fly from Chicago to San Diego. 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. United Airlines, American Airlines, Southwest Airlines, Frontier (O'Malley the Mallard Duck Livery) depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through 21 Air, Air Canada, Alaska Horizon, Allegiant Air, British Airways, Contour Aviation, Copa Airlines, Delta Air Lines (SkyTeam Livery), FedEx, Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Air, KLM, Lufthansa, National Airlines, NetJets, SkyWest Airlines, Spirit Airlines, Sun Country Airlines, UPS, WestJet.

A direct flight lasts an average of 4h 10m, during which time the aircraft covers a distance of 2787 km.

The price of flights Chicago — San Diego starts from $44.

Planes fly Chicago — San Diego 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 San Diego — Montgomery Field, Miramar MS, North Island NAS, San Diego International Airport, Brown Field Municipalcipal, Gillespie Field, McClellan-Palomar Airport.

The following flights fly between Chicago and San Diego: UA264, AA2343, WN2014, WN2014, WN2014, WN3175, WN3851, WN3175, UA660, AA2131, UA2294, UA2294, AA2309, F91855, WN2365, UA2683, WN2365, WN2365, WN2365, UA2417, UA2417, UA2417, AA1543, AA1543, AA1543, WN3466, UA8124, WN1275, WN1275, AA1861, AA1861, AA1861

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

The following airlines have direct flights Chicago — San Diego: United Airlines, American Airlines, Southwest Airlines, Frontier (O'Malley the Mallard Duck Livery).

All the following airlines flights Chicago — San Diego: 21 Air, Air Canada, Alaska Horizon, Allegiant Air, American Airlines, British Airways, Contour Aviation, Copa Airlines, Delta Air Lines (SkyTeam Livery), FedEx, Frontier (O'Malley the Mallard Duck Livery), Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Air, KLM, Lufthansa, National Airlines, NetJets, SkyWest Airlines, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Airlines, UPS, WestJet.

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