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Cheap Flights from Chicago to San Diego International

Compare Chicago to San Diego International flight deals

Find the cheapest month or even day of the year to fly to San Diego International

Book the best San Diego International fare with no extra fees

Flight deals from Chicago to San Diego International

Looking for a cheap last-minute deal or the best return flight from Chicago to San Diego International Airport? If you want to travel next month, return fares start from R 3,633. Find the lowest prices on one-way and return tickets right here.
San Diego.R 1,584 per passenger.Departing Tue, 21 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 21 Jul, arriving in San Diego International.Price includes taxes and charges.From R 1,584, select.
San Diego.R 1,601 per passenger.Departing Fri, 5 Jun.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri, 5 Jun, arriving in San Diego International.Price includes taxes and charges.From R 1,601, select.
San Diego.R 1,642 per passenger.Departing Tue, 1 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 1 Sep, arriving in San Diego International.Price includes taxes and charges.From R 1,642, select.
San Diego.R 1,651 per passenger.Departing Wed, 27 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 27 May, arriving in San Diego International.Price includes taxes and charges.From R 1,651, select.
San Diego.R 1,837 per passenger.Departing Tue, 25 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 25 Aug, arriving in San Diego International.Price includes taxes and charges.From R 1,837, select.
San Diego.R 1,958 per passenger.Departing Thu, 13 Aug.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 13 Aug, arriving in San Diego International.Price includes taxes and charges.From R 1,958, select.
San Diego.R 1,973 per passenger.Departing Wed, 3 Jun.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Wed, 3 Jun, arriving in San Diego International.Price includes taxes and charges.From R 1,973, select.
San Diego.R 2,050 per passenger.Departing Sat, 30 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 30 May, arriving in San Diego International.Price includes taxes and charges.From R 2,050, select.
San Diego.R 2,235 per passenger.Departing Thu, 24 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 24 Sep, arriving in San Diego International.Price includes taxes and charges.From R 2,235, select.
San Diego.R 2,866 per passenger.Departing Sun, 18 Oct.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from Chicago O'Hare International on Sun, 18 Oct, arriving in San Diego International.Price includes taxes and charges.From R 2,866, select.
San Diego.R 2,868 per passenger.Departing Thu, 2 Jul.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from Chicago O'Hare International on Thu, 2 Jul, arriving in San Diego International.Price includes taxes and charges.From R 2,868, select.
San Diego.R 2,880 per passenger.Departing Fri, 15 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 15 Jan, arriving in San Diego International.Price includes taxes and charges.From R 2,880, select.
San Diego.R 2,888 per passenger.Departing Fri, 13 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 13 Nov, arriving in San Diego International.Price includes taxes and charges.From R 2,888, select.
San Diego.R 2,892 per passenger.Departing Tue, 30 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 30 Mar, arriving in San Diego International.Price includes taxes and charges.From R 2,892, select.
San Diego.R 3,055 per passenger.Departing Fri, 4 Dec.One-way flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from Chicago O'Hare International on Fri, 4 Dec, arriving in San Diego International.Price includes taxes and charges.From R 3,055, select.
San Diego.R 21,006 per passenger.Departing Fri, 2 Apr.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 2 Apr, arriving in San Diego International.Price includes taxes and charges.From R 21,006, select.

Find the cheapest month to fly from Chicago to San Diego International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to San Diego International flights are currently cheapest in July.
May
from R 1,651
Jun
from R 1,601
Jul
from R 1,584
Aug
from R 1,837
Sep
from R 1,642
Oct
from R 2,866
Nov
from R 2,888
Dec
from R 3,055
Jan
from R 2,880
Feb
Find prices
Mar
from R 2,892
Apr
from R 21,006

Direct flights from Chicago to San Diego International

Chicago to San Diego International: Alternative routes

Compare routes from Chicago to San Diego below. You may find an airport to fly into that's cheaper, faster, or easier than San Diego International.

San Diego International

4km from central San Diego
ClosestCheapest
from R 1,584
Search flights

McClellan-Palomar

48km from central San Diego
from R 2,604
Search flights

Chicago to San Diego: Flight information

The things to know before you go.
Cheapest flight foundR 1,584
Cheapest month to flyJuly
Average flight time4 hrs, 22 mins
Most popular airlineAmerican Airlines
Average flights per week339

Finding cheap flights from Chicago to San Diego International: Frequently asked questions

The best price we found for a return flight from Chicago to San Diego International is R 2,852. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 22 minutes is the average flight time from Chicago to San Diego International.
American Airlines, Southwest Airlines and British Airways fly direct from Chicago to San Diego International.
As of May 2026, there are 339 flights per week flying from Chicago to San Diego International.
The cheapest month to fly from Chicago to San Diego International is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Diego International Airport on Tuesday, 26 May 2026.
Yes – the average flight time is 4 hours and 22 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Diego International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Diego is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from Chicago to San Diego International Airport (SAN): What you need to know

  • Your trip gets off the ground at one of Chicago's main airports, Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore the options for booking a flight from Chicago to San Diego International Airport (SAN) setting off from either of these.

  • Take off on a direct Chicago to San Diego International Airport flight and you'll be travelling for an average of 4 hours 25 minutes.

  • The timezone in San Diego is UTC-8, which is two hours behind Chicago. San Diego International Airport is located in San Diego.

  • Choose from 77 direct services a week between Chicago O'Hare International Airport (ORD) and San Diego International Airport (SAN). This is the most popular route when departing from Chicago.

  • Leave plenty of time to catch your flight from Chicago to SAN. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Hopping on a plane during a peak month like July? High seasons (like Thanksgiving, Christmas and spring break) can add another hour at check-in and security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) makes it easy to travel directly to your destination. Nonstop flights from Chicago to San Diego International Airport (SAN) leave from this terminal.

  • Well-known airlines that offer direct flights from Chicago to San Diego International Airport leaving from ORD include:

  • United is the airline with the highest number of bookings for flights from ORD to SAN.

  • United is the most consistent performer for punctuality on this route.

  • ORD is about 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take 30 minutes or so to get there, depending on traffic. If you're taking public transport, expect the travel time to be around 45 minutes.

  • Want an easy start to your journey? Stay near Chicago O'Hare International Airport. Whether you're catching an early flight from Chicago to San Diego International Airport or just don't want to be rushed, these hotels have you covered:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights stick to their scheduled arrival time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Planning to catch a flight from Chicago Midway International Airport (MDW)? Direct Chicago to San Diego International Airport (SAN) plane tickets can be booked from this popular hub.

  • Southwest Airlines operates direct flights from Chicago to SAN out of MDW. Book your favourite aisle (or window) seat and get to your destination without any detours.

  • On the MDW to SAN route, Southwest Airlines is the airline most travellers rely on.

  • With 73.55% of its services arriving as planned, Southwest Airlines is the top on-time carrier flying between Chicago Midway International Airport and San Diego International Airport.

  • MDW is around 16 kilometres from central Chicago. It takes 25 minutes or so to get to the airport driving from the city centre. Public transport takes approximately 30 minutes.

  • Want to enjoy an extra night away before your Chicago to SAN flight? Unwind in a hotel near Chicago Midway International Airport before your break officially starts. These stays are calling your name:

  • When it comes to keeping flights punctual, Chicago Midway International Airport has an on-time arrival performance of 76%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From central Chicago, RFD is around 145 kilometres away. It'll take you roughly 1 hour 40 minutes to get to the airport by car and 2 hours or so if you use public transport.

  • Make catching an early Chicago to San Diego International Airport flight the easiest part of your trip. Book a room at one of these hotels close to Chicago Rockford International Airport and get to the check-in counter with time to spare:

  • The on-time performance rate of RFD is 71%. In simpler terms, that's how often flights departing this airport arrive as planned.

  • The street address of Chicago Rockford International Airport is 2 Airport Cir.

About San Diego International Airport (SAN)

  • The last thing you need is a long journey to your hotel if you're arriving on a late flight from Chicago to San Diego International Airport. Stay at one of these accommodation options near SAN instead:

  • To get the lowest price, reserve your ride around two weeks ahead of your Chicago to San Diego International Airport flight.

  • The street address for SAN is N Harbour Dr.

Getting from San Diego International Airport (SAN) to central San Diego

  • From San Diego International Airport, central San Diego is around 5 kilometres away. It takes about 15 minutes to reach the city centre by car.

  • It typically takes 25 minutes if you're using public transport.

How to find the cheapest flights from Chicago to San Diego International Airport (SAN)

  • R 1,584 is currently the lowest price for a one-way ticket from Chicago to San Diego International Airport. Return flights start from R 2,852. These fares may change depending on demand.

  • Don't leave things to the last minute. You're more likely to walk away with cheap flights from Chicago to SAN if you book in advance. Airlines often offer some great early bird discounts.

  • Cheap Chicago to San Diego International Airport tickets are easier to find when you have flexibility in your schedule. Use the 'Whole month' search tool to compare fares across each month and then pick the cheapest day.

  • Finding a cheap plane ticket from Chicago to SAN is a breeze with Price Alerts. All you need to do is set up one of these automatic alerts and we'll notify you as soon as prices go down.

  • Filters make it easier to track down a bargain for your flight from Chicago to San Diego International Airport. Pick the departure times, airlines and number of stops that line up with your plans. Then sort the results by 'Cheapest' to zero in on the cheapest fare fast.

The best time to fly from Chicago to San Diego International Airport (SAN)

  • December is the quietest month for flights from Chicago to San Diego International Airport (SAN), while July is the busiest. Choose the best time to visit San Diego based on whether you like a laid-back vibe or a lively atmosphere.

  • The warmest month in San Diego is August, with temperatures ranging between 16ºC (61ºF) and 27ºC (81ºF). Lock in your Chicago to SAN plane ticket then if this is the type of weather you enjoy.

  • February sees temperatures of between 8ºC (46ºF) and 22ºC (72ºF). Look for cheap tickets from Chicago to San Diego International Airport around that time if you like travelling in cooler conditions.

More about San Diego

  • Start your San Diego trip right by choosing the ideal place to stay. Once you've booked your flight from Chicago to San Diego International Airport, explore our selection of accommodation options including:

  • Your visit to San Diego wouldn't be complete without a bit of sightseeing. Leading attractions worth exploring include San Diego Zoo, San Diego Balboa Park and USS Midway Museum.

Explore more of the United States

  • San Diego has plenty to offer, but there are so many other corners of the United States waiting to be explored. About 177 kilometres northwest of San Diego, a trip to Los Angeles will keep you on the move. Start with leading sights like Hollywood Sign, Universal Studios Hollywood and Hollywood Bowl.

  • If you're looking to explore another corner of the United States, head for Long Beach, about 145 kilometres northwest of San Diego. The Queen Mary, Museum of Latin American Art (MOLAA) and Long Beach Lighthouse are among its highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.