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Cheap flights from Chicago to San Diego

64 nonstop flights a week, 6 of them today. Operated by 4 airlines, about 4h 35m in the air, 1,731 mi (2,786 km). Tickets from $145, nonstop from $144.

Flights from Chicago to San Diego

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Chicago to San Diego

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Chicago to San Diego

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $117 22 January 2027, with a connection Cheapest nonstop $144 14 November 2026, Alaska Airlines Cheapest in the next 7 days $144 14 November, Sat Cheapest weekend departure $144 Sat, 14 November 2026
Cheapest day of the week Friday $145 on average over the next 120 days
Cheapest month January 2027 tickets from $117

Chicago to San Diego at a glance

flight time, from 4h 10m to 14h 49m
4h 35m
straight-line distance
1,731 mi (2,786 km)
flights a week
64
flights today
6
first and last departure
05:20 - 10:03
lowest price, with a connection, 15 January
$145
lowest nonstop price
$144
airlines
4

Chicago to San Diego ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: January 2027, tickets from $117. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is December 2026: from $169. The average across months is $143.

Chicago to San Diego flight schedule

64 flights a week, 6 today, 41 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 1484
Southwest Airlines
05:20 Chicago Midway International
13:45 San Diego International, terminal 1
10h 25m
Mon, Thu, Fri, Sun
AA 2343
American Airlines
06:45 , terminal 3
09:20 San Diego International, terminal 2
4h 35m
Daily
Boeing 737-800
UA 2428
United Airlines
07:00 , terminal 1
09:27 San Diego International, terminal 2
4h 27m
Daily
Airbus A320
AS 1470
Alaska Airlines
07:20 , terminal 2
10:03 San Diego International, terminal 2
4h 43m
Daily
Boeing 737-900
AS 1470
Alaska Airlines
07:26 , terminal 2
10:07 San Diego International, terminal 2
4h 41m
Mon, Fri, Sat, Sun
Boeing 737
WN 133
Southwest Airlines
07:40 Chicago Midway International
13:00 San Diego International, terminal 1
7h 20m
Sun
Boeing 737-800
WN 133
Southwest Airlines
07:50 Chicago Midway International
13:05 San Diego International, terminal 1
7h 15m
Mon, Thu, Fri, Sun
AA 2831
American Airlines
08:05 , terminal 3
10:54 San Diego International, terminal 2
4h 49m
Sat
Airbus A321
AA 2831
American Airlines
08:10 , terminal 3
10:59 San Diego International, terminal 2
4h 49m
Mon, Thu, Fri, Sun
Boeing 737-800
AA 1543
American Airlines
08:20 , terminal 3
10:56 San Diego International, terminal 2
4h 36m
Daily
Boeing 737-800
UA 660
United Airlines
08:50 , terminal 1
11:27 San Diego International, terminal 2
4h 37m
Daily
Airbus A320
AA 2131
American Airlines
09:59 , terminal 3
12:46 San Diego International, terminal 2
4h 47m
Mon, Thu, Fri, Sun
Airbus A321
AA 2131
American Airlines
10:00 , terminal 3
12:47 San Diego International, terminal 2
4h 47m
Sat
Airbus A321
WN 836
Southwest Airlines
10:00 Chicago Midway International
13:55 San Diego International, terminal 1
5h 55m
Mon, Thu, Fri, Sun
Boeing 737-800
AA 1802
American Airlines
10:03 , terminal 3
12:39 San Diego International, terminal 2
4h 36m
Daily
Airbus A321

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 3020
Southwest Airlines
06:00 Chicago Midway International
08:30 San Diego International, terminal 1
4h 30m
Seasonal
Boeing 737
WN 594
Southwest Airlines
08:15 Chicago Midway International
10:40 San Diego International, terminal 1
4h 25m
Seasonal
WN 1456
Southwest Airlines
09:50 Chicago Midway International
12:15 San Diego International, terminal 1
4h 25m
Seasonal
Boeing 737
AS 1470
Alaska Airlines
07:27 , terminal 2
10:12 San Diego International, terminal 2
4h 45m
Seasonal
Boeing 737-900
AA 877
American Airlines
08:05 , terminal 3
10:44 San Diego International, terminal 2
4h 39m
Seasonal
Boeing 737-800
AS 1470
Alaska Airlines
07:00 , terminal 2
09:46 San Diego International, terminal 2
4h 46m
Seasonal
Boeing 737-900
UA 2054
United Airlines
07:45 , terminal 1
20:34 San Diego International, terminal 2
14h 49m
Seasonal
Boeing 737-900
AS 1454
Alaska Airlines
07:40 , terminal 2
10:19 San Diego International, terminal 2
4h 39m
Seasonal
Boeing 737-900
UA 660
United Airlines
08:45 , terminal 1
11:21 San Diego International, terminal 2
4h 36m
Seasonal
Airbus A320
AA 2026
American Airlines
06:40 , terminal 3
09:21 San Diego International, terminal 2
4h 41m
Seasonal
Boeing 737-800
AA 1543
American Airlines
08:07 , terminal 3
10:48 San Diego International, terminal 2
4h 41m
Seasonal
Boeing 737-800
WN 1563
Southwest Airlines
10:00 Chicago Midway International
13:50 San Diego International, terminal 1
5h 50m
Seasonal
AA 1543
American Airlines
10:04 , terminal 3
12:43 San Diego International, terminal 2
4h 39m
Seasonal
Airbus A321
WN 356
Southwest Airlines
10:05 Chicago Midway International
12:35 San Diego International, terminal 1
4h 30m
Seasonal
Boeing 737
WN 2750
Southwest Airlines
06:55 Chicago Midway International
09:25 San Diego International, terminal 1
4h 30m
Seasonal
AA 2131
American Airlines
06:45 , terminal 3
09:20 San Diego International, terminal 2
4h 35m
Seasonal
Boeing 737-800
WN 2697
Southwest Airlines
07:55 Chicago Midway International
11:55 San Diego International, terminal 1
6h
Seasonal
Boeing 737-800
AA 562
American Airlines
08:29 , terminal 3
11:05 San Diego International, terminal 2
4h 36m
Seasonal
Boeing 737
UA 660
United Airlines
08:55 , terminal 1
11:17 San Diego International, terminal 2
4h 22m
Seasonal
Airbus A320
WN 2750
Southwest Airlines
10:00 Chicago Midway International
12:25 San Diego International, terminal 1
4h 25m
Seasonal
Boeing 737
AA 562
American Airlines
06:45 , terminal 3
09:20 San Diego International, terminal 2
4h 35m
Seasonal
Boeing 737-800
UA 2428
United Airlines
07:40 , terminal 1
10:11 San Diego International, terminal 2
4h 31m
Seasonal
Boeing 737
AA 1543
American Airlines
08:29 , terminal 3
11:05 San Diego International, terminal 2
4h 36m
Seasonal
Boeing 737
WN 2963
Southwest Airlines
05:45 Chicago Midway International
08:15 San Diego International, terminal 1
4h 30m
Seasonal
Boeing 737
WN 4063
Southwest Airlines
10:05 Chicago Midway International
12:40 San Diego International, terminal 1
4h 35m
Seasonal
Boeing 737
AS 1723
Alaska Airlines
08:00 , terminal 2
10:25 San Diego International, terminal 2
4h 25m
Seasonal
Boeing 737-900
WN 2963
Southwest Airlines
05:20 Chicago Midway International
07:50 San Diego International, terminal 1
4h 30m
Seasonal
WN 1688
Southwest Airlines
10:05 Chicago Midway International
14:00 San Diego International, terminal 1
5h 55m
Seasonal
UA 660
United Airlines
09:00 , terminal 1
11:22 San Diego International, terminal 2
4h 22m
Seasonal
Airbus A320
WN 4221
Southwest Airlines
06:00 Chicago Midway International
08:25 San Diego International, terminal 1
4h 25m
Seasonal
Boeing 737
AA 470
American Airlines
09:40 , terminal 3
12:13 San Diego International, terminal 2
4h 33m
Seasonal
Boeing 737-800
WN 4221
Southwest Airlines
07:20 Chicago Midway International
09:45 San Diego International, terminal 1
4h 25m
Seasonal
Boeing 737
WN 4221
Southwest Airlines
07:05 Chicago Midway International
09:30 San Diego International, terminal 1
4h 25m
Seasonal
Boeing 737
AA 2733
American Airlines
06:45 , terminal 3
09:04 San Diego International, terminal 2
4h 19m
Seasonal
Boeing 737-800
AA 470
American Airlines
10:02 , terminal 3
12:26 San Diego International, terminal 2
4h 24m
Seasonal
Airbus A321
AA 2484
American Airlines
06:45 , terminal 3
09:15 San Diego International, terminal 2
4h 30m
Seasonal
Boeing 737-800
WN 2747
Southwest Airlines
05:05 Chicago Midway International
07:15 San Diego International, terminal 1
4h 10m
Seasonal
Boeing 737
WN 2748
Southwest Airlines
09:55 Chicago Midway International
12:10 San Diego International, terminal 1
4h 15m
Seasonal
Boeing 737
AA 2484
American Airlines
06:49 , terminal 3
09:04 San Diego International, terminal 2
4h 15m
Seasonal
Boeing 737-800
AA 470
American Airlines
10:05 , terminal 3
12:27 San Diego International, terminal 2
4h 22m
Seasonal
Airbus A321
AA 2482
American Airlines
10:02 , terminal 3
12:21 San Diego International, terminal 2
4h 19m
Seasonal
Airbus A321

Days of the week are taken from the schedule for the next 14 days; schedules change by season. San Diego is 2 hours behind Chicago. The search shows seat availability and the price for your date.

Airlines flying Chicago to San Diego

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

American Airlines31 a week United Airlines14 a week Southwest Airlines12 a week Alaska Airlines7 a week

Airports

Where flights from Chicago to San Diego depart and land

Departure from Chicago

Chicago Midway International MDW

12 flights a week, 9 mi (14 km) from the city centre

About the airport

Arrival in San Diego

San Diego International SAN

64 flights a week, terminals 1, 2, 2 mi (4 km) from the city centre

About the airport

Frequently asked questions

How long is the flight from Chicago to San Diego?
A nonstop flight takes 4 hours 35 minutes on average, from 4h 10m to 14h 49m depending on the flight.
How far is San Diego from Chicago?
1,731 mi (2,786 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to San Diego?
American Airlines (31 a week), United Airlines (14 a week), Southwest Airlines (12 a week) and Alaska Airlines (7 a week).
How many flights a day are there from Chicago to San Diego?
6 flights today and 64 a week, about 9.1 a day on average.
When are the first and last flights from Chicago to San Diego?
The first departure is at 05:20 (WN1484), the last at 10:03 (AA1802). Local time.
What is the cheapest month to fly from Chicago to San Diego?
January 2027: tickets from $117. The most expensive is December 2026, from $169.
What is the cheapest upcoming date to fly from Chicago to San Diego?
22 January 2027 (Friday): from $117 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to San Diego?
Alaska Airlines: nonstop tickets from $144 on 14 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and San Diego?
San Diego is 2 hours behind Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to San Diego leave from?
Chicago Midway International (12 a week).