Flight Routes from San Diego to Chicago

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

Trip type
Cheapest roundtrip flight
from€335
Fastest flight
non-stop flights
164x / 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 Airlines
  2. American Airlines
  3. Alaska Airlines
  4. Southwest Airlines

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

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

offers
Active filtersnone
Matching outbound flightsSAN–CHI · 28 of 28
fromto
dep.arr.
durationstopovers
  1. October 4 – 10, 2026
  2. October 11 – 17, 2026
  3. October 18 – 24, 2026
    1. SANORD
      nonstop
      1. American Airlines
    2. SANMDW
      nonstop
      1. Southwest Airlines
    3. SANMDW
      nonstop
      1. Southwest Airlines
    4. SANMDW
      nonstop
      1. Southwest Airlines
    5. SANORD
      nonstop
      1. United Airlines
    6. SANMDW
      nonstop
      1. Southwest Airlines
    7. SANORD
      nonstop
      1. Alaska Airlines
    8. SANMDW
      nonstop
      1. Southwest Airlines
    9. SANORD
      nonstop
      1. United Airlines
    10. SANMDW
      nonstop
      1. Southwest Airlines
    11. SANMDW
      nonstop
      1. Southwest Airlines
    12. SANMDW
      nonstop
      1. Southwest Airlines
    13. SANMDW
      nonstop
      1. Southwest Airlines
    14. SANORD
      nonstop
      1. American Airlines
    15. SANMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Frequently Asked Questions (FAQ)

      How long is the flight from San Diego to Chicago?
      A nonstop flight from San Diego to Chicago typically takes around 3 hours 54 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 9 hours 12 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
      Are there nonstop flights from San Diego to Chicago?
      Yes, there are nonstop flights from San Diego to Chicago, averaging around 23 to 24 flights per day, operated by, among others, United Airlines, American Airlines and Alaska Airlines. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
      Which airlines fly from San Diego to Chicago?
      Direct flights from San Diego to Chicago are operated by, among others, United Airlines, American Airlines and Alaska Airlines. Connecting flights with one stop are also available, for example with Delta (via Atlanta, Los Angeles). 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 San Diego to Chicago?
      Nonstop flights from San Diego to Chicago 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 San Diego to Chicago?
      From San Diego to Chicago, there are on average around 23 to 24 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 San Diego to Chicago?
      From San Diego to Chicago, there are around 165 to 166 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 San Diego to Chicago depart?
      The earliest nonstop flight from San Diego to Chicago usually departs at 6:15 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 Chicago.
      When does the last flight from San Diego to Chicago depart?
      The last nonstop flight from San Diego to Chicago usually departs at 10:45 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 San Diego and Chicago

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