A river with a yellow boat, surrounded by tall buildings and a bridge.

AED 1,100 Cheap Flights from San Diego (SAN) to Chicago (CHI)

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

Prices were available within the past 7 days and start at AED 1,100 for one-way flights, for the period specified. Prices and availability are subject to change.
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,100
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,100 Found 4 hours ago
Delta
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,100
One way
Found 4 hours ago
Select Delta flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,100 Found 4 hours ago
Southwest Airlines
Tuesday, 13 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,130
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Tuesday, 13 October, 2026 from San Diego to Chicago, priced at AED 1,130 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,180
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,180 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,200
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,200 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,210
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,210 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,230
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,230 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,280
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,280 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,310
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,310 Found 4 hours ago
Southwest Airlines
Tuesday, 13 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,320
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Tuesday, 13 October, 2026 from San Diego to Chicago, priced at AED 1,320 Found 4 hours ago
Delta
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,330
One way
Found 4 hours ago
Select Delta flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,330 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,390
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,390 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,410
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,410 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,420
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,420 Found 4 hours ago
Delta
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,530
One way
Found 4 hours ago
Select Delta flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,530 Found 4 hours ago
Delta
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,540
One way
Found 4 hours ago
Select Delta flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,540 Found 4 hours ago
Delta
Tuesday, 13 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,620
One way
Found 4 hours ago
Select Delta flight, departing Tuesday, 13 October, 2026 from San Diego to Chicago, priced at AED 1,620 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,730
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,730 Found 4 hours ago
Southwest Airlines
Wednesday, 14 October, 2026
SAN
San Diego
MDW
Chicago
AED 1,750
One way
Found 4 hours ago
Select Southwest Airlines flight, departing Wednesday, 14 October, 2026 from San Diego to Chicago, priced at AED 1,750 Found 4 hours ago
United
Wednesday, 14 October, 2026
CLD
Carlsbad
MDW
Chicago
AED 3,130
One way
Found 4 hours ago
Select United flight, departing Wednesday, 14 October, 2026 from Carlsbad to Chicago, priced at AED 3,130 Found 4 hours ago

Travel information

Origin airport
San Diego Intl. Airport
Destination airport
Chicago Midway Airport
Distance
2,777 km away
Airlines serving
Southwest Airlines, Delta, Frontier Airlines
Popular airline
Southwest Airlines
Roundtrip price
AED 1,100
Average flight time
4 hours 16 mins
*Available to One Key members.