Flights to San Diego from Chicago S$224~

Airlines that fly from Chicago to San Diego

    Plan, book, fly with confidence
  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to San Diego (CHI-SAN)

Prices were available within the past 7 days and start at S$224 for one-way flights and S$423 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 23 Jan - Wed, 29 Jan
ORD
Chicago
SAN
San Diego
S$423 Return, found 1 day ago
S$423
Return
found 1 day ago
Select Delta flight, departing Thu, 23 Jan from Chicago to San Diego, returning Wed, 29 Jan, priced at S$423 found 1 day ago
Delta
Thu, 23 Jan - Wed, 29 Jan
ORD
Chicago
SAN
San Diego
S$426 Return, found 1 day ago
S$426
Return
found 1 day ago
Select Delta flight, departing Thu, 23 Jan from Chicago to San Diego, returning Wed, 29 Jan, priced at S$426 found 1 day ago
Delta
Thu, 23 Jan - Wed, 29 Jan
ORD
Chicago
SAN
San Diego
S$427 Return, found 1 day ago
S$427
Return
found 1 day ago
Select Delta flight, departing Thu, 23 Jan from Chicago to San Diego, returning Wed, 29 Jan, priced at S$427 found 1 day ago
Delta
Sun, 15 Dec - Tue, 24 Dec
ORD
Chicago
SAN
San Diego
S$430 Return, found 12 hours ago
S$430
Return
found 12 hours ago
Select Delta flight, departing Sun, 15 Dec from Chicago to San Diego, returning Tue, 24 Dec, priced at S$430 found 12 hours ago
Delta
Sun, 15 Dec - Tue, 24 Dec
ORD
Chicago
SAN
San Diego
S$513 Return, found 12 hours ago
S$513
Return
found 12 hours ago
Select Delta flight, departing Sun, 15 Dec from Chicago to San Diego, returning Tue, 24 Dec, priced at S$513 found 12 hours ago
Delta
Sun, 15 Dec - Tue, 24 Dec
ORD
Chicago
SAN
San Diego
S$522 Return, found 12 hours ago
S$522
Return
found 12 hours ago
Select Delta flight, departing Sun, 15 Dec from Chicago to San Diego, returning Tue, 24 Dec, priced at S$522 found 12 hours ago
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals
*Available to Expedia members.