Flight Routes from Chicago to San Diego

Compare cheap outbound and return flights from Chicago (CHI) to San Diego (SAN) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€360
Fastest outbound flight
Fastest inbound flight
non-stop flights
156x / week
Flight distance
2,791 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL
Most popular airlines
  1. United AirlinesUnited Airlines
  2. American AirlinesAmerican Airlines
  3. Southwest AirlinesSouthwest Airlines
  4. Alaska AirlinesAlaska Airlines

Flight schedule from Chicago (CHI) to San Diego (SAN)

Select a travel date in the flight schedule for the route from Chicago (CHI) to San Diego (SAN) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–SAN · 47 of 47
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. MDWSAN
      nonstop
      1. Southwest Airlines
    2. MDWSAN
      nonstop
      1. Southwest Airlines
    3. MDWSAN
      nonstop
      1. Southwest Airlines
    4. MDWSAN
      nonstop
      1. Southwest Airlines
    5. ORDSAN
      nonstop
      1. American Airlines
    6. ORDSAN
      nonstop
      1. United Airlines
    7. ORDSAN
      nonstop
      1. Alaska Airlines
    8. ORDSAN
      nonstop
      1. Alaska Airlines
    9. ORDSAN
      nonstop
      1. United Airlines
    10. ORDSAN
      nonstop
      1. United Airlines
    11. MDWSAN
      nonstop
      1. Southwest Airlines
    12. MDWSAN
      nonstop
      1. Southwest Airlines
    13. MDWSAN
      nonstop
      1. Southwest Airlines
    14. ORDSAN
      nonstop
      1. American Airlines
    15. MDWSAN
      nonstop
      1. Southwest Airlines

      Tips and tricks to help you find cheap flights from Chicago to San Diego

      Favorite airline: Spirit Airlines
      The favorite airline for flights from Chicago to San Diego is Spirit Airlines.
      Spirit Airlines
      34 %
      Alaska Airlines
      22 %
      United Airlines
      22 %
      Direct flights are more expensive
      On this route, direct flights are $179.00 more expensive than flights with a stopover.
      non stop flight
      1 stop
      04h 15min
      14h 15min
      $352
      $173
      Favourite connection: via Las Vegas
      The most popular route is via Las Vegas and is booked by 36 % of all travelers.
      Route
      bookings
      1 stopover Las Vegas - McCarran International Airport, NV
      14h 15min, from $173
      36 %
      Direct flights
      04h 15min, from $352
      28 %
      1 stopover San Francisco International Airport, CA
      12h 42min, from $421
      15 %

      Important flight information

      Frequently Asked Questions (FAQ)

      How long is the flight from Chicago to San Diego?
      A nonstop flight from Chicago to San Diego typically takes around 4 hours 22 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 9 hours 8 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
      Are there nonstop flights from Chicago to San Diego?
      Yes, there are nonstop flights from Chicago to San Diego, averaging around 22 to 23 flights per day, operated by, among others, United Airlines, American Airlines and Southwest. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
      Which airlines fly from Chicago to San Diego?
      Direct flights from Chicago to San Diego are operated by, among others, United Airlines, American Airlines and Southwest. Connecting flights with one stop are also available, for example with Delta (via Atlanta). If travel time matters to you, a direct flight is usually the most convenient option. Connecting flights often give you more choice of departure times and airlines.
      On which days are there nonstop flights from Chicago to San Diego?
      Nonstop flights from Chicago to San Diego operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
      How many flights are there per day from Chicago to San Diego?
      From Chicago to San Diego, there are on average around 22 to 23 flights per day. This usually means you have a good choice of departure times. If you are flexible, you can easily compare times, prices, and airlines.
      How many flights per week are there from Chicago to San Diego?
      From Chicago to San Diego, there are around 156 to 157 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
      When does the first flight from Chicago to San Diego depart?
      The earliest nonstop flight from Chicago to San Diego usually departs at 5:30 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in San Diego.
      When does the last flight from Chicago to San Diego depart?
      The last nonstop flight from Chicago to San Diego usually departs at 11:05 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.

      Discover more flights around Chicago and San Diego

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport San Diego - Lindberg Field International, CA (SAN)
      Destination country Flights to United States
      Departure airport - Destination country Chicago-IL, all airports - United States