Flights from San Diego to Chicago from $284
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Airfare Deals San Diego to Chicago
On HolidayPrice.com you will find 4 direct and 3 connecting flights from San Diego to Chicago at a price of from $284. 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 SAN - CHI flight schedule to find best flight time, convenient departure and arrival airports.
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The cost of airline tickets from San Diego to Chicago (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 Chicago.
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Cheap flights from San DiegoCheap flights to Chicago
Airline tickets to United States
One way flight from San Diego to Chicago
Below are the prices of tickets for direct one-way flights from San Diego to Chicago. The cheapest flight from San Diego to Chicago starts from $284 – the departure date for this flight is 21 May 2025.
03.06.2025
Tuesday
from $88
Kupi.com
Economy
Found 2025-05-16
1 Stopover
6 hours 37 min
Find Flights
Round trip from San Diego to Chicago
You can buy a round-trip ticket from San Diego to Chicago (United States) and back using the table below. The best offer starts from $129, the flight dates are: there on 20 May 2025 year and back on 21 May 2025 year.
*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.
Flight Schedule San Diego to Chicago 2025
The current flight schedule for the route from San Diego to Chicago 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 11 flights every day, from 3hours 50min. Local departure and arrival times are indicated.
*Schedule is indicated only for direct scheduled flights and low-cost airlines.
Flight Information
Flying to Chicago from San Diego takes 04:14 minutes (excluding transfers). The distance between San Diego and Chicago is 1728 miles (2782 kilometers). Planes depart from San Diego between 00:00 and 23:59. The fastest flight from the company United Airlines with flight number UA 1900. Flies for just 03:40 minutes with departure from San Diego and arrival in O'Hare.
Average flight time
04:14 min
Distance
1728 mi
The earliest flight
00:00
The latest flight
23:59
The fastest flight
03:40
Airlines
Direct flight
There are 4 airlines that fly directly from San Diego to Chicago. The most popular company carrying out non-stop flights is Southwest Airlines.
- Southwest Airlines: WN 2324, WN 2392, WN 5383
- United Airlines: UA 913, UA 794, UA 555
- American Airlines: AA 956, AA 134, AA 2680
- Spirit Airlines: NK 564, NK 356
*Flight number
Flights with Transfers
Flights with transfers from San Diego to Chicago can be bought from 3 airlines:
- Southwest Airlines: Dallas, San Francisco, Las Vegas
- United Airlines: Long Beach
- American Airlines: Phoenix, Dallas
*Transit cities
Airports
Airports serving the air communication between San Diego and Chicago. You can fly to Chicago from 1 San Diego airports. Planes arrive at 2 airport in Chicago.
San Diego airports:
San Diego ~ 3 km* from $ 27Chicago airports:
Chicago Midway ~ 14 km* from $ 44O'Hare ~ 25 km* from $ 48*Distance from the airport to the city center
Aircraft
You can fly from San Diego to Chicago 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 Chicago from San Diego. The best options are to fly through: Dallas, San Francisco, Las Vegas, Denver, Sacramento, Long Beach, Phoenix, Baltimore, Kansas City, Indianapolis.
Cheap airline tickets from San Diego to United States
Here is a list of flights from San Diego 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.
San Diego - New York UA 395
United Airlines Airbus A319
07:35
San Diego
in a way 4 hours 59 min
Direct
12:34
Newark Liberty
Flights
from $88 21 May 2025
from $88 21 May 2025
San Diego - Los Angeles AA 6062
American Airlines Embraer EMB 175
16:20
San Diego
in a way 0 hours 40 min
Direct
17:00
Los Angeles
Flights
from $48 20 May 2025
from $48 20 May 2025
San Diego - Miami AA 1209
American Airlines Boeing 737-800
07:15
San Diego
in a way 4 hours 45 min
Direct
12:00
Miami
Flights
from $82 20 May 2025
from $82 20 May 2025
San Diego - Chicago UA 1900
United Airlines Airbus A320
00:20
San Diego
in a way 3 hours 40 min
Direct
04:00
O'Hare
Flights
from $284 21 May 2025
from $284 21 May 2025
San Diego - San Francisco UA 1001
United Airlines Boeing 737
03:50
San Diego
in a way 1 hours 10 min
Direct
05:00
San Francisco
Flights
from $27 26 May 2025
from $27 26 May 2025
Flights from United States to Chicago
Here are the cheapest flight bookings from United States to Chicago 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 - Chicago UA 761
United Airlines Boeing 737-800
13:00
LaGuardia
in a way 2 hours 0 min
Direct
15:00
O'Hare
Flights
from $33 20 May 2025
from $33 20 May 2025
Los Angeles - Chicago UA 910
United Airlines Boeing 737-800
10:23
Los Angeles
in a way 3 hours 37 min
Direct
14:00
O'Hare
Flights
from $48 20 May 2025
from $48 20 May 2025
Miami - Chicago AA 2796
American Airlines Boeing 767-300
17:05
Miami
in a way 2 hours 55 min
Direct
20:00
O'Hare
Flights
from $36 22 May 2025
from $36 22 May 2025
Miami - Chicago WN 1626
Southwest Airlines Boeing 737
13:35
Fort Lauderdale Executive Airport
in a way 3 hours 0 min
Direct
16:35
Chicago Midway
Flights
from $36 22 May 2025
from $36 22 May 2025
San Francisco - Chicago UA 1800
United Airlines Airbus A319
04:15
San Francisco
in a way 3 hours 45 min
Direct
08:00
O'Hare
Flights
from $83 20 May 2025
from $83 20 May 2025
Tips for buying a ticket
San Diego – Chicago – San Diego round-trip route are always cheaper than tickets purchased there and back separately.
To start searching for tickets, Specify dates.