Flights from Chicago to San Diego from $53

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Flights San Diego → Chicago
Flights Schedule   Cheap Tickets   Airlines   Airports

Airfare Deals Chicago to San Diego

On HolidayPrice.com you will find 4 direct and 3 connecting flights from Chicago to San Diego at a price of from $53. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out CHI - SAN flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Chicago to San Diego (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to San Diego.

You might be interested in this:

Cheap flights from Chicago
Cheap flights to San Diego
Airline tickets to United States

One way flight from Chicago to San Diego

Below are the prices of tickets for direct one-way flights from Chicago to San Diego. The cheapest flight from Chicago to San Diego starts from $53 – the departure date for this flight is 20 May 2025.

*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Chicago to San Diego

You can buy a round-trip ticket from Chicago to San Diego (United States) and back using the table below. The best offer starts from $125, the flight dates are: there on 22 May 2025 year and back on 26 May 2025 year.

*Prices include: baggage, hand luggage, airline fees and charges.
From Chicago to San Diego from $154! Airfare Deals by Frontier Airlines
from $154 left 0 days
Sales dates 01 May 2025 Flight dates: 19 May 2025
Chicago - San Diego One way, Economy - from $154
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Flight Schedule Chicago to San Diego 2025

The current flight schedule for the route from Chicago to San Diego for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 12 flights every day, from 4hours 19min. Local departure and arrival times are indicated.
06:48 → 09:09
American Airlines AA2131 American Airlines AA2131
ORD → SAN
- - - - - Sa -
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06:50 → 09:19
American Airlines AA2131 American Airlines AA2131
ORD → SAN
Mo Tu We Th Fr - Su
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07:55 → 10:25
Southwest Airlines WN581 Southwest Airlines WN581
MDW → SAN
- - - - - Sa -
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08:15 → 10:40
Southwest Airlines WN816 Southwest Airlines WN816
MDW → SAN
Mo - - Th Fr - -
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08:30 → 11:00
Southwest Airlines WN1404 Southwest Airlines WN1404
MDW → SAN
- - - - - - Su
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08:40 → 11:10
Southwest Airlines WN3595 Southwest Airlines WN3595
MDW → SAN
- Tu We - - - -
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09:05 → 11:42
United Airlines UA660 United Airlines UA660
ORD → SAN
Mo Tu We Th Fr Sa Su
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10:08 → 12:39
American Airlines AA2131 American Airlines AA2131
ORD → SAN
Mo Tu We Th - - Su
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10:12 → 12:43
American Airlines AA2189 American Airlines AA2189
ORD → SAN
Mo Tu We Th Fr - Su
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11:20 → 13:56
United Airlines UA2294 United Airlines UA2294
ORD → SAN
Mo Tu We Th Fr Sa Su
Check price
12:05 → 16:45
Southwest Airlines WN3339 Southwest Airlines WN3339
MDW → SAN
- - - - - - Su
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12:20 → 14:50
Southwest Airlines WN2272 Southwest Airlines WN2272
MDW → SAN
Mo - - Th Fr - -
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Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to San Diego from Chicago takes 04:14 minutes (excluding transfers). The distance between Chicago and San Diego is 1728 miles (2782 kilometers). Planes depart from Chicago between 00:00 and 23:50. The fastest flight from the company Southwest Airlines with flight number WN 1137. Flies for just 04:00 minutes with departure from Chicago Midway and arrival in San Diego.

time

Average flight time

04:14 min

distance

Distance

1728 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:50

Airplane

The fastest flight

04:00

Airlines

Direct flight

There are 4 airlines that fly directly from Chicago to San Diego. The most popular company carrying out non-stop flights is Southwest Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Chicago to San Diego can be bought from 3 airlines:

  • Southwest Airlines: Denver, Las Vegas
  • United Airlines: Long Beach
  • American Airlines: Long Beach, Tulsa, Las Vegas

*Transit cities

Airports

Airports serving the air communication between Chicago and San Diego. You can fly to San Diego from 2 Chicago airports. Planes arrive at 1 airport in San Diego.

Chicago airports:

Chicago Midway  ~ 14 km* from $ 59O'Hare  ~ 25 km* from $ 31

San Diego airports:

San Diego  ~ 3 km* from $ 26

*Distance from the airport to the city center

Aircraft

You can fly from Chicago to San Diego on board of 4 airlines that utilize 7 aircraft models.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900

Connecting cities

The list of cities on transfer flights to San Diego from Chicago. The best options are to fly through: Denver, Long Beach, Las Vegas, Tulsa.

Denver
Long Beach
Las Vegas
Tulsa

Cheap airline tickets from Chicago to United States

Here is a list of flights from Chicago to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Chicago - New York AA 2382 American Airlines Boeing 737-800
01:13 O'Hare
in a way 1 hours 47 min Direct
03:00 Newark Liberty
Flights
from $32 21 May 2025
Chicago - Los Angeles AA 2744 American Airlines Airbus A321
20:03 O'Hare
in a way 3 hours 57 min Direct
00:00 Los Angeles
Flights
from $47 20 May 2025
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from $36 20 May 2025
Chicago - San Francisco AA 1312 American Airlines Boeing 737-800
17:55 O'Hare
in a way 4 hours 5 min Direct
22:00 Norman Y. Mineta San Jose
Flights
from $63 21 May 2025
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $41 26 May 2025

All flights from Chicago

Flights from United States to San Diego

Here are the cheapest flight bookings from United States to San Diego made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - San Diego UA 1827 United Airlines Boeing 737-700
23:35 Newark Liberty
in a way 5 hours 25 min Direct
05:00 San Diego
Flights
from $105 21 May 2025
Los Angeles - San Diego AA 6089 American Airlines Embraer EMB 175
19:35 Los Angeles
in a way 0 hours 25 min Direct
20:00 San Diego
Flights
from $49 26 May 2025
Miami - San Diego AA 2674 American Airlines Airbus A321
02:44 Miami
in a way 5 hours 3 min Direct
07:47 San Diego
Flights
from $51 26 May 2025
Chicago - San Diego WN 1137 Southwest Airlines Boeing 737-800
14:05 Chicago Midway
in a way 4 hours 0 min Direct
18:05 San Diego
Flights
from $53 20 May 2025
San Francisco - San Diego WN 179 Southwest Airlines Boeing 737-700
07:25 Norman Y. Mineta San Jose
in a way 1 hours 10 min Direct
08:35 San Diego
Flights
from $28 26 May 2025

All flights to San Diego

Tips for buying a ticket

Chicago – San Diego – Chicago round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Chicago to San Diego
San Diego city

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