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Find cheap one-way flights from Chicago to San Diego starting at US$45.

Book one-way or return flights from Chicago to San Diego from as little as US$45. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to book flights from Chicago to San Diego?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Cheapest airlines flights from Chicago to San Diego

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From US$45
Spirit Airlines
From US$56
American Airlines
From US$88
Sun Country Airlines
From US$94
Southwest Airlines
From US$94
Alaska Airlines
From US$107
Delta Air Lines
From US$112
Allegiant Air
From US$138
United Airlines
From US$152
Jetblue Airways
From US$315
ANA airlines

Find more flights and airlines

Find cheap flights from Chicago to San Diego by different airports

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to San Diego.

  • Cheapest
    Frontier Airlines
    MDW
    05:30
    13h 45m
    1 transfer
    SAN
    17:15
    Midway International Airport - San Diego International Airport
    Wed, Apr 17Frontier Airlines
    US$45
  • Frontier Airlines
    ORD
    23:05
    13h 11m
    1 transfer
    SAN
    10:16
    O'Hare International Airport - San Diego International Airport
    Tue, Apr 9Frontier Airlines
    US$63
  • Allegiant Air
    RFD
    12:23
    7h 12m
    1 transfer
    SAN
    17:35
    Chicago Rockford International Airport - San Diego International Airport
    Thu, Mar 28Allegiant Air
    US$138
  • Allegiant Air
    RFD
    12:23
    7h 12m
    1 transfer
    SAN
    17:35
    Chicago Rockford International Airport - San Diego International Airport
    Thu, Mar 28Allegiant Air
    US$138
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to San Diego (SAN) the cheapest?

    Airlines adjust prices for flights from Chicago to San Diego based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Chicago (CHI) to San Diego (SAN) cost?

    According to Trip.com's data, the lowest price is around $367.
  • How long does it take to fly from Chicago (CHI) to San Diego (SAN) and what is the distance?

    It takes around 4 hours 21 minutes to fly from Chicago (CHI) to San Diego (SAN).
  • What is the transportation method from the main airport to downtown in San Diego?

    • The distance from San Diego International Airport to downtown is about 3km. It takes about 20 minutes by taxi.
  • What are the most popular airlines that fly from Chicago (CHI) to San Diego (SAN)?

Chicago to San Diego Flight Information

Cheapest nonstop flight price

$44

Cheapest round-trip ticket price

$130

Off-season for travel

December

Peak season for travel

June