Cheap flights San Diego — Chicago (SAN — CHI)

Good to know - Cheap tickets San Diego — Chicago

Cheapest flight found $44
Minimal flight time 3h 55m
Flight distance 2787 km
Most popular airline United Airlines

Airfare San Diego – Chicago by month

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

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

Departure Arrival Flight days Flight Airlines Flight time Airports
06:15 12:40 daily AA1494 American Airlines 4h 25m San Diego International Airport — O'Hare International Airport Select dates
06:30 12:35 wed, thu WN4602 Southwest Airlines 4h 5m San Diego International Airport — Chicago Midway International Airport Select dates
06:35 12:40 mon, tue, thu, fri, sun WN2153 Southwest Airlines 4h 5m San Diego International Airport — Chicago Midway International Airport Select dates
07:00 13:00 sat WN3768 Southwest Airlines 4h 0m San Diego International Airport — Chicago Midway International Airport Select dates
07:00 13:13 daily UA2343 United Airlines 4h 13m San Diego International Airport — O'Hare International Airport Select dates
07:00 13:11 mon, tue, wed UA2343 United Airlines 4h 11m San Diego International Airport — O'Hare International Airport Select dates
07:10 13:10 sat WN2153 Southwest Airlines 4h 0m San Diego International Airport — Chicago Midway International Airport Select dates
10:51 17:05 daily UA2677 United Airlines 4h 14m San Diego International Airport — O'Hare International Airport Select dates
10:52 17:03 fri, sat, sun UA2677 United Airlines 4h 11m San Diego International Airport — O'Hare International Airport Select dates
10:56 17:09 thu, fri, sat, sun UA1748 United Airlines 4h 13m San Diego International Airport — O'Hare International Airport Select dates
All routes

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

2025-12-31 one-way

2025-12-31 one-way

Flights San Diego — Chicago

The selection of cheap flights San Diego — Chicago

Here you can find and purchase the cheapest flights San Diego — Chicago from $44 and San Diego — Chicago — San Diego from $36.

The price of the flight San Diego — Chicago (United States) — San Diego from $36 (round-trip).

The average price of the flight San Diego — Chicago (United States) — San Diego $418 (round-trip).

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

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

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

Minimal flight time from San Diego to Chicago 3h 55m.

LowCostClub always do a comparison of airfares San Diego — Chicago with several airlines (include American Airlines, Southwest Airlines, United 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 San Diego — Chicago. Last week, for instance, the cheapest round-trip prices stood at $36 while the cheapest one-way price that was available within the last week cost $44

Routes from nearby cities to Chicago

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

The most frequent flight to Chicago is from Los Angeles. The cheapest airfare can be purchased with a flight from Phoenix from $31. The nearest airports from San Diego with a flight to Chicago are in Prescott.

Popular International routes from San Diego

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 San Diego

FAQ about San Diego — Chicago

Yes, they do: AA1494, WN4602, WN2153, WN3768, UA2343, UA2677, UA1748, AS1186, WN1748, AA2131, AS1478, UA1779, AA2065, AA1861, WN3683, QR8596, UA2624

Yes, you can fly from San Diego to Chicago. San Diego has 7 airports (Montgomery Field, Miramar MS, North Island NAS, San Diego International Airport, Brown Field Municipalcipal, Gillespie Field, McClellan-Palomar Airport) for flights. American Airlines, Southwest Airlines, United Airlines, Alaska Airlines, Qatar Airways depart from San Diego on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, AlphaSky, Amazon Air, British Airways, Contour Aviation, Copa Airlines, Delta Air Lines, FedEx, Frontier (Sage the Pygmy Rabbit Livery), Japan Airlines, Jet Linx Aviation, JetBlue, JSX, Kalitta Air, Kalitta Charters, Lufthansa, National Airlines, NetJets, Phoenix Air, SkyWest Airlines, Sun Country Airlines, UPS, WestJet.

A direct flight lasts an average of 3h 55m, during which time the aircraft covers a distance of 2787 km.

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

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

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

The following flights fly between San Diego and Chicago: AA1494, WN4602, WN2153, WN3768, UA2343, UA2343, WN2153, UA2677, UA2677, UA1748, WN3768, AS1186, WN1748, AA2131, AA2131, AA2131, AA2131, WN1748, AS1478, AS1478, AS1478, UA1779, AA2065, AA1861, WN3683, WN4602, WN4602, WN4602, QR8596, UA2624, QR8596

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

The following airlines have direct flights San Diego — Chicago: American Airlines, Southwest Airlines, United Airlines, Alaska Airlines, Qatar Airways.

All the following airlines flights San Diego — Chicago: Air Canada, Alaska Airlines, AlphaSky, Amazon Air, American Airlines, British Airways, Contour Aviation, Copa Airlines, Delta Air Lines, FedEx, Frontier (Sage the Pygmy Rabbit Livery), Japan Airlines, Jet Linx Aviation, JetBlue, JSX, Kalitta Air, Kalitta Charters, Lufthansa, National Airlines, NetJets, Phoenix Air, Qatar Airways, SkyWest Airlines, Southwest Airlines, Sun Country Airlines, United Airlines, UPS, WestJet.

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