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Cheap Flights from Chicago (CHIA) to San Diego (SANA)

Compare Chicago to San Diego flight deals

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

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Flight deals from Chicago to San Diego

Looking for a cheap last-minute deal or the best return flight from Chicago to San Diego? Find the lowest prices on one-way and return tickets right here.
San Diego.$166 per passenger.Departing Thu, 2 Oct, returning Tue, 7 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Oct, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 7 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $166, select.
San Diego.$166 per passenger.Departing Sat, 20 Sep, returning Mon, 22 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 20 Sep, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 22 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $166, select.
San Diego.$166 per passenger.Departing Mon, 18 Aug, returning Tue, 26 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 18 Aug, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 26 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $166, select.
San Diego.$192 per passenger.Departing Tue, 29 Jul, returning Fri, 15 Aug.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 29 Jul, arriving in San Diego International.Inbound indirect flight with Spirit Airlines, departs from San Diego International on Fri, 15 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $192, select.
San Diego.$210 per passenger.Departing Wed, 20 Aug, returning Fri, 5 Sep.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 20 Aug, arriving in San Diego International.Inbound indirect flight with Spirit Airlines, departs from San Diego International on Fri, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $210, select.
San Diego.$213 per passenger.Departing Tue, 29 Jul, returning Wed, 30 Jul.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 29 Jul, arriving in San Diego International.Inbound indirect flight with Spirit Airlines, departs from San Diego International on Wed, 30 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $213, select.
San Diego.$229 per passenger.Departing Wed, 27 Aug, returning Mon, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 27 Aug, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $229, select.
San Diego.$239 per passenger.Departing Sat, 20 Sep, returning Sun, 5 Oct.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 20 Sep, arriving in San Diego International.Inbound indirect flight with Spirit Airlines, departs from San Diego International on Sun, 5 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $239, select.

Find the cheapest month to fly from Chicago to San Diego

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to San Diego flights are currently cheapest in August.
Jul
from $213
Aug
from $166
Sep
from $166
Oct
from $166
Nov
from $260
Dec
from $485
Jan
from $559
Feb
from $560
Mar
from $560
Apr
from $589
May
Find prices
Jun
Find prices

Direct flights from Chicago to San Diego

Alternative Chicago to San Diego routes

Looking for the cheapest, fastest or easiest route from Chicago to San Diego? You could fly into the following airports instead.

Chicago to San Diego: Flight information

The things to know before you go.
Cheapest flight found$166
Cheapest month to flyAugust
Average flight time4 hrs, 22 mins
Most popular airlineSouthwest Airlines
Average flights per week304

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

There are 2 airports in San Diego: San Diego International and McClellan-Palomar.
The best price we found for a return flight from Chicago to San Diego is $166. 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.
Southwest Airlines, American Airlines and Alaska Airlines fly direct from Chicago to San Diego.
As of July 2025, there are 304 flights per week flying from Chicago to San Diego.
The cheapest month to fly from Chicago to San Diego is usually August.
If you're flying from Chicago, the cheapest airport near San Diego is San Diego International – which is 4.1 km away from the centre of San Diego. We've found flights into this airport from $166.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Diego on Monday, 18 August 2025.
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 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.
In July, the average temperature is usually around 22°C. August is typically the warmest month in San Diego, when it usually averages around 28°C. You can expect the least rain in June. The coldest month is December, with temperatures averaging 10°C. The rainiest month is February.
The cheapest airline that flies to San Diego is Southwest Airlines .

Flying from Chicago to San Diego: what you need to know

  • Your next exciting journey begins at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to San Diego leaving from either of these bases.

  • San Diego International Airport (SAN) and McClellan-Palomar Airport (CLD) are the chief entry points to San Diego.

  • Around 4 hours 20 minutes is how long you'll be travelling on a direct Chicago to San Diego flight.

  • San Diego is two hours behind Chicago and observes the UTC-7 timezone.

  • O'Hare International Airport (ORD) to San Diego International Airport (SAN) is the most popular route that connects these two cities. There are 58 departures a week to pick from. If you prefer a later start to the day, the last flight from Chicago to San Diego is with United Airlines at 21:30. Go for the first ORD to SAN departure with United Airlines at 07:10 to maximise your time in San Diego.

  • To ensure you catch your Chicago to San Diego flight, leave enough time for things like check-in and baggage drop. Turning up two hours before international departures and an hour before domestic flights is the general rule to follow.

  • Popular months like August or holiday periods such as Thanksgiving and Christmas will mean bigger lines at check-in and security. Be on the safe side and head to the terminal even earlier. Arriving two hours before domestic flights and four hours ahead of international departures is a smart idea.

How to find the cheapest flights from Chicago to San Diego

  • At the moment, $69 is the lowest price we've seen for a one-way ticket from Chicago to San Diego. The cheapest price for a return flight is $166. Remember fares may change due to demand at the time of booking.

  • Book two months before travelling. Pricing trends show that this is the ideal window for finding cheap Chicago to San Diego flights.

  • Organise your trip for May. That's the best month for scoring a great bargain on plane tickets from Chicago to San Diego. If you have flexibility with your dates, use the 'Whole month' tool to see the cheapest price across each month.

  • Stay on top of deals for cheap flights from Chicago to San Diego by creating a Price Alert. We'll send you an email or notification through the app when a new low fare is offered.

  • Tailor your flights using filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Cheapest' or 'Best' Chicago to San Diego flights.

Flying from Chicago

O'Hare International Airport (ORD)

  • You can catch a direct flight from Chicago to San Diego departing from O'Hare International Airport (ORD). Begin your journey at ORD and come in for landing at San Diego International Airport (SAN).

  • Lock in your Chicago to San Diego plane tickets with United Airlines. This airline is a popular option for direct flights from ORD.

  • The journey from central Chicago to ORD takes around 55 minutes by public transport. If you ride-share, drive or get a cab, you'll cover the 26 kilometres in 35 minutes or so, depending on traffic conditions.

  • Planning to catch an early flight from Chicago to San Diego? Avoid the stress of rushing to the airport (and sneak in some extra snooze time) by choosing one of these stays close to O'Hare International Airport:

  • When it comes to O'Hare International Airport's on-time performance, 74.85% of flights complete their journey on time.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can take a nonstop flight from Chicago to San Diego departing from Chicago Midway International Airport (MDW). Begin your travels at MDW and hop off the plane at San Diego International Airport (SAN).

  • Southwest Airlines offers direct Chicago to San Diego plane tickets from MDW. Book your favourite aisle (or window) seat and arrive at your destination without any detours.

  • Using public transport, you can travel from central Chicago to MDW in around 45 minutes. The airport is roughly 14 kilometres away. Driving will take you about 20 minutes.

  • Want to treat yourself to an extra night away before boarding your flight from Chicago to San Diego? Relax in a hotel near Chicago Midway International Airport before your holiday officially starts. Consider one of these stays:

  • 77.88% of flights leaving Chicago Midway International Airport arrive within the expected time frame.

  • You'll find MDW at 5700 South Cicero.

Arriving in San Diego

San Diego International Airport (SAN)

  • San Diego International Airport (SAN) is approximately 3 kilometres from the centre of San Diego. If you're catching a cab or a ride-share, the drive takes around 10 minutes.

  • If you're taking public transport, expect a journey time of about 20 minutes.

  • Consider booking a hotel close to SAN if you're coming in on a late flight from Chicago to San Diego. Settle into one of these options and avoid the hassle of a long transfer:

  • Follow your own route with a San Diego International Airport rental car. Book your wheels from Thrifty, Dollar or Budget and experience more of San Diego and beyond.

  • Lock in the best deal by reserving your vehicle from San Diego International Airport around two weeks ahead of your trip.

  • You'll find SAN at N Harbour Dr.

McClellan-Palomar Airport (CLD)

  • Central San Diego is approximately 48 kilometres from McClellan-Palomar Airport (CLD). Once your flight from Chicago to San Diego has touched down and you've navigated your way to arrivals, expect a drive of about 40 minutes.

  • If you're catching public transport, it'll take about 2 hours 15 minutes.

  • Budget, Hertz and Avis make collecting a McClellan-Palomar Airport rental car quick and easy. These providers are located around or in the terminal and will get you on your way in no time.

  • Avoid the long lines and paperwork at the rental desk by completing your booking beforehand. Secure your ride from CLD ahead of time so you can just grab the keys and go.

Best time to go to San Diego

  • July is the most popular month for flights from Chicago to San Diego. To steer clear of the crowds, visit San Diego in May.

  • When booking your Chicago to San Diego tickets, consider the kind of weather forecast you're hoping for. August is the warmest month in San Diego, with temperatures ranging from 17ºC (63ºF) to 28ºC (82ºF).

  • Search for cheap flights from Chicago to San Diego in February if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 7ºC (45ºF) and 23ºC (73ºF) on average.

More about San Diego

  • After booking your flight from Chicago to San Diego, decide where you'll be dropping your bags. Make one of these accommodation options your base for exploring San Diego:

  • There are so many things to explore in this city it can be difficult to know where to begin. San Diego Zoo, USS Midway Museum and SeaWorld San Diego are highlights which should be on any good San Diego itinerary.

Explore more of United States

  • San Diego has loads to offer, but there are so many other corners of United States you should also see. About 177 kilometres north-west of San Diego, a trip to Los Angeles will keep your itinerary packed. Start with attractions like Griffith Observatory, The Broad and La Brea Tar Pits & Museum.

  • Around 483 kilometres east of San Diego, Phoenix is another favourite stop in United States. Start your sightseeing at Desert Botanical Garden, Heard Museum and Papago Park.

Plan the rest of your trip from Chicago to San Diego

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