Cheap flights from Chicago to San Diego

Flights overview

Useful information for finding cheap flights from Chicago to San Diego and booking your next trip
Cheapest round-trip flights $157
American Nonstop 5 hr Sat, Feb 28 — Sat, Mar 7
The cheapest round-trip flight from Chicago to San Diego is currently $157
Cheapest one-way flight $79
American Nonstop 5 hr Wed, Feb 18
The cheapest one-way flight from Chicago to San Diego is currently $79
Last-minute weekend getaway $394
Frontier 1 stop 8 hr Fri, Jan 30 — Mon, Feb 2
The cheapest last-minute weekend getaway from Chicago to San Diego is currently $394
Cheapest business class flights $727
Alaska Nonstop 5 hr Thu, Apr 16 — Wed, Apr 22
The cheapest business class round-trip flight from Chicago to San Diego is currently $727
Fastest flight 4 hr 15 min The fastest nonstop flight from Chicago to San Diego takes 4 hr 15 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to San Diego is typically September. The most expensive month to fly is typically May.
September
Cheapest
Typical prices: $130–190
May
Most expensive
Typical prices: $180–265

Popular airlines from Chicago to San Diego

  • Southwest
    Nonstop
    from $157
    Typical price: $195–475
    14 weekly nonstop flights
    MDW - SAN Every day
    2568 weekly connecting flights
    MDW, ORD - SAN Every day
  • United
    Nonstop
    from $157
    Typical price: $175–460
    25 weekly nonstop flights
    ORD - SAN Every day
    362 weekly connecting flights
    ORD - SAN Every day
  • American
    Nonstop
    from $157
    Typical price: $180–510
    14 weekly nonstop flights
    ORD - SAN Every day
    305 weekly connecting flights
    ORD - SAN Every day
  • Alaska
    Nonstop
    from $157
    Typical price: $195–560
    14 weekly nonstop flights
    ORD - SAN Every day
    19 weekly connecting flights
    ORD - SAN Every day
  • Delta
    from $237
    Typical price: $255–600
    340 weekly connecting flights
    MDW, ORD - SAN Every day
  • Frontier
    from $180
    Typical price: $155–355
    28 weekly connecting flights
    MDW, ORD - SAN Every Mon, Wed, Thu, Fri, Sat, Sun

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 27 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near San Diego

  • San Diego International Airport (SAN)
    San Diego United States 10 min 2 mi
  • Tijuana International Airport (TIJ)
    Tijuana Mexico 37 min 16 mi
  • Los Angeles International Airport (LAX)
    Los Angeles United States 2 hr 2 min 111 mi
  • John Wayne Airport (SNA)
    Santa Ana United States 1 hr 21 min 78 mi

Frequently asked questions about flying from Chicago to San Diego

The cheapest flights from Chicago to San Diego are usually in September. Typical ticket prices in September range from $130 to $190.
The cheapest round-trip flight from Chicago to San Diego recently found on Google Flights was with American from $157. The cheapest one-way flight was with American from $79.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San Diego is $157, flying from Apr 18 to Apr 25.
  • The cheapest United flight from Chicago to San Diego is $157, flying from Mar 7 to Mar 14.
  • The cheapest American flight from Chicago to San Diego is $157, flying from Feb 28 to Mar 7.
  • The cheapest Alaska flight from Chicago to San Diego is $157, flying from Apr 25 to May 2.
  • The cheapest Delta flight from Chicago to San Diego is $237, flying from Feb 26 to Mar 4.
  • The cheapest Frontier flight from Chicago to San Diego is $180, flying from Apr 9 to Apr 15.
The cheapest round-trip flight from Chicago to San Diego starts at $157 from Sat, Feb 28 to Sat, Mar 7. The cheapest one-way flight starts at $79 and departs on Wed, Feb 18.
4 hr 15 min is the shortest flight time from Chicago to San Diego.
Jun–Aug is when most people visit San Diego, where the weather's temperate year-round. Beaches are less crowded Dec–Feb, which bring cooler temperatures but brighter sun. Whale-watching season is from mid-Dec–mid-Mar. Major annual events include Comic-Con International (Jul), a massive comic book convention with workshops and film screenings. Fleet Week (autumn) is a large military appreciation event featuring Navy ship tours, an air show and more.
It's easy to use Google Flights to find the cheapest days to fly from Chicago to San Diego.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to San Diego really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to San Diego.

In terms of nonstop flights, United is the most popular. United offers 25 nonstop flights and 362 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 2,568 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .

Other popular airlines flying from Chicago to San Diego are:
  • American offers 14 nonstop flights and 305 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .
  • Alaska offers 14 nonstop flights and 19 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .
  • Delta offers 340 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .
  • Frontier offers 28 connecting flights per week. Frontier flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to San Diego International Airport (SAN) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and San Diego.
The cheapest round-trip flight from Chicago to San Diego recently found on Google Flights was with American from $157. The cheapest one-way flight was with American from $79.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San Diego is $157, flying from Apr 18 to Apr 25.
  • The cheapest United flight from Chicago to San Diego is $157, flying from Mar 7 to Mar 14.
  • The cheapest American flight from Chicago to San Diego is $157, flying from Feb 28 to Mar 7.
  • The cheapest Alaska flight from Chicago to San Diego is $157, flying from Apr 25 to May 2.
  • The cheapest Delta flight from Chicago to San Diego is $237, flying from Feb 26 to Mar 4.
  • The cheapest Frontier flight from Chicago to San Diego is $180, flying from Apr 9 to Apr 15.
Southwest, United, American and Alaska fly direct from Chicago to San Diego.
  • There are 14 Southwest direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 25 United direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 14 American direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 14 Alaska direct flights from Chicago to San Diego per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and San Diego at price $394 is offered by Frontier from Fri, Jan 30 to Mon, Feb 2.
Southwest, United, American and Alaska fly direct from Chicago to San Diego.
  • There are 14 Southwest direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 25 United direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 14 American direct flights from Chicago to San Diego per week. Flights are available every day.
  • There are 14 Alaska direct flights from Chicago to San Diego per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Chicago to San Diego on a daily basis.
The cheapest direct (nonstop) round-trip flights between Chicago and San Diego start at $157 from Sat, Feb 28 to Sat, Mar 7 with American.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to San Diego, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and San Diego start at $727 from Thu, Apr 16 to Wed, Apr 22 with Alaska.
The cheapest economy class round-trip flights between Chicago and San Diego start at $157 from Sat, Feb 28 to Sat, Mar 7.
To book business class trips from Chicago to San Diego, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and San Diego starts at $394 from Fri, Jan 30 to Mon, Feb 2 with Frontier.
The cheapest last-minute deal between Chicago and San Diego at price $394 is offered by Frontier from Fri, Jan 30 to Mon, Feb 2.
To find last-minute flight deals from Chicago to San Diego, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

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