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Cheap flights Chicago — San Diego

Chicago (CHI, US) San Diego (SAN, US)
from $85 2 786 km ~3h 47m 5 flights found 3 airlines cheapest on Thursday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $85 on 17.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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Th
Fr
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Su
December 2026
Mo
Tu
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January 2027
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Tu
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Prices found for 3 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
17 Dec 2026, Thu
Frontier Airlines F9 1483
16:00
ORD O'Hare International Airport
21:33
SAN San Diego International Airport
5h 33m 1 stop
Kiwi.com
$85
View this ticket
17 Dec 2026, Thu
Alaska Airlines AS 1447
23:17
ORD O'Hare International Airport
04:02
SAN San Diego International Airport
4h 45m Direct
Kiwi.com
$108
View this ticket
17 Nov 2026, Tue
Southwest Airlines WN 1456
19:10
MDW Chicago Midway International Airport
23:35
SAN San Diego International Airport
4h 25m Direct
Farera
$134
View this ticket
18 Nov 2026, Wed
Southwest Airlines WN 1071
00:45
MDW Chicago Midway International Airport
05:15
SAN San Diego International Airport
4h 30m Direct
Farera
$134
View this ticket
Route characteristics
Distance
2 786 km
Flight time
3h 47m
Time difference
-2h
Minimum price
from $85 (17.12.2026)
Average price
$118
Maximum price
$134
Cheapest day
Thursday
Departure airports (2)
MDW Chicago Midway International Airport ORD O'Hare International Airport
Arrival airports (1)
SAN San Diego International Airport
Airlines (3)
F9 Frontier Airlines AS Alaska Airlines WN Southwest Airlines
Agencies (3)
Kiwi.com Farera Clickavia
Prices by day of week
Tuesday
$134
avg $134
Wednesday
$134
avg $134
Thursday
$85
avg $97
Cheapest
Price trend by month
November 2026
from $134
avg $134
2 flights
December 2026
from $85
avg $97
2 flights
Airlines — cheapest prices 3
Frontier Airlines
Frontier Airlines
Low-cost 1 flights · 1 days
$85
Alaska Airlines
Alaska Airlines
2 flights · 2 days
$108
Southwest Airlines
Southwest Airlines
Low-cost 2 flights · 2 days
$134
Where to buy tickets 3
Kiwi.com
2 tickets · 1 days
from $85
Farera
2 tickets · 2 days
from $134
Clickavia
1 tickets · 1 days
from $157
Airports

From — Chicago (2)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport

To — San Diego (1)

  • SAN San Diego International Airport
Other destinations from Chicago
Las Vegas
US · Hub
Denver
US · Hub
Nashville
US
Fort Lauderdale
US
Minneapolis
US · Hub
St Louis
US
Atlanta
US · Hub
Philadelphia
US · Hub
Tampa
US
Baltimore
US
Phoenix
US
New Orleans
US
Frequently asked questions about the route Chicago — San Diego
How long is the flight from Chicago to San Diego?
Approximate flight time — 3h 47m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Chicago to San Diego?
The straight-line distance — 2 786 km.
How much do flights from Chicago to San Diego cost?
The minimum price over 3 months — from $85 on 17.12.2026.
What is the average ticket price?
The average price — $118. Range: $85 — $134.
What is the time difference between Chicago and San Diego?
The difference — -2h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport), ORD (O'Hare International Airport).
To which airports in San Diego do flights arrive?
To San Diego: SAN (San Diego International Airport).
Which airlines fly this route?
This route is served by 3 airlines: Frontier Airlines, Alaska Airlines, Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $108. Total direct flights found: 3.
Which day of the week is cheapest?
The cheapest day of the week — Thursday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Chicago — San Diego

Flights Chicago — San Diego is a popular route. The straight-line distance is 2 786 km. Flight time 3h 47m. Time difference -2h.

From Chicago (CHI) flights depart from 2 airports: MDW, ORD. To San Diego (SAN) — 1 arrival airport: SAN.

3 airlines operate on this route: Frontier Airlines, Alaska Airlines, Southwest Airlines.

The minimum price for the next 3 months — from $85 (17.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $118, ranging from $85 to $134. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Thursday.

Other destinations in United States from Chicago
Denver
US
Las Vegas
US
Nashville
US
Fort Lauderdale
US
Minneapolis
US
St Louis
US
Atlanta
US
Philadelphia
US

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