$99 Cheap American Airlines flights Chicago (ORD) to San Diego (SAN)

View $99 flight on Mon, Mar 9, 2026Opens in a new window

$99 Cheap American Airlines flights Chicago (ORD) to San Diego (SAN)

Prices were available within the past 7 days and start at $99 for one-way flights and $214 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Mar 21 - Wed, Mar 25
ORD
Chicago
SAN
San Diego
$214 Roundtrip, found 1 day ago
$214
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 21 from Chicago to San Diego, returning Wed, Mar 25, priced at $214 found 1 day ago
American Airlines
Sat, Mar 21 - Wed, Mar 25
ORD
Chicago
SAN
San Diego
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 21 from Chicago to San Diego, returning Wed, Mar 25, priced at $224 found 1 day ago
American Airlines
Sat, Mar 21 - Wed, Mar 25
ORD
Chicago
SAN
San Diego
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 21 from Chicago to San Diego, returning Wed, Mar 25, priced at $228 found 1 day ago
American Airlines
Sat, Mar 21 - Wed, Mar 25
ORD
Chicago
SAN
San Diego
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 21 from Chicago to San Diego, returning Wed, Mar 25, priced at $230 found 1 day ago
American Airlines
Sat, Mar 21 - Wed, Mar 25
ORD
Chicago
SAN
San Diego
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 21 from Chicago to San Diego, returning Wed, Mar 25, priced at $243 found 1 day ago

Find the cheapest month to fly from Chicago (ORD) to San Diego (SAN)

February is typically the cheapest month to fly

From $91 - $166 per traveler.

Alternative airports near San Diego

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Diego Intl. SAN. Cheapest and Closest option available. Average driving time to city center is 5 minutes. Flights from $195
SAN
San Diego Intl.
CheapestClosest
Average driving time to city center5 min
Flights from $195
Flights from Chicago (ORD) to San Diego (SAN)
Origin airport
O'Hare Intl.
Destination airport
San Diego Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Hawaiian Airlines, Southwest Airlines, United
Popular airline
Alaska Airlines
Distance
2752 km
Average flight time
3 hours 1 min