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Cheap Flights from Chicago 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? If you want to travel next month, return fares start from $303. Find the lowest prices on one-way and return tickets right here.
San Diego.$303 per passenger.Departing Sat, 12 Sep, returning Thu, 17 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 12 Sep, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Thu, 17 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $303, select.
San Diego.$303 per passenger.Departing Tue, 27 Oct, returning Thu, 5 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 27 Oct, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $303, select.
San Diego.$339 per passenger.Departing Sat, 17 Oct, returning Thu, 22 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 17 Oct, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Thu, 22 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $339, select.
San Diego.$340 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 29 Aug, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Sat, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.
San Diego.$340 per passenger.Departing Tue, 25 Aug, returning Mon, 31 Aug.Return 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.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.
San Diego.$340 per passenger.Departing Wed, 23 Sep, returning Sat, 3 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 23 Sep, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.
San Diego.$340 per passenger.Departing Tue, 3 Nov, returning Tue, 10 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 3 Nov, arriving in San Diego International.Inbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 10 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $340, select.
San Diego.$345 per passenger.Departing Wed, 16 Sep, returning Tue, 22 Sep.Return flight with Alaska Airlines.Outbound direct flight with Alaska Airlines departs from Chicago O'Hare International on Wed, 16 Sep, arriving in San Diego International.Inbound direct flight with Alaska Airlines departs from San Diego International on Tue, 22 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $345, select.
San Diego.$368 per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 29 Aug, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $368, select.
San Diego.$368 per passenger.Departing Sat, 3 Oct, returning Sat, 10 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 3 Oct, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Sat, 10 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $368, select.
San Diego.$368 per passenger.Departing Sat, 7 Nov, returning Sat, 14 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Nov, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 14 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $368, select.
San Diego.$369 per passenger.Departing Sat, 31 Oct, returning Tue, 3 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 31 Oct, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Tue, 3 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $369, select.
San Diego.$385 per passenger.Departing Sat, 29 Aug, returning Sun, 30 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 29 Aug, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Sun, 30 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $385, select.
San Diego.$385 per passenger.Departing Sun, 27 Sep, returning Sat, 3 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 27 Sep, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $385, select.
San Diego.$407 per passenger.Departing Wed, 9 Dec, returning Sat, 12 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 9 Dec, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Sat, 12 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $407, select.
San Diego.$414 per passenger.Departing Wed, 20 Jan, returning Wed, 10 Feb.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 20 Jan, arriving in San Diego International.Inbound direct flight with United departs from San Diego International on Wed, 10 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From $414, 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 September.
Aug
from $340
Sep
from $303
Oct
from $339
Nov
from $340
Dec
from $407
Jan
from $442
Feb
from $555
Mar
from $635
Apr
from $660
May
from $635
Jun
from $635
Jul
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.

San Diego International

4km from central San Diego
ClosestCheapest
from $303
Search flights

McClellan-Palomar

48km from central San Diego
from $609
Search flights

Chicago to San Diego: Flight information

The things to know before you go.
Cheapest flight found$303
Cheapest month to flySeptember
Average flight time4 hrs, 27 mins
Most popular airlineAmerican Airlines
Average flights per week1,972

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 $303. 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 26 minutes is the average flight time from Chicago to San Diego.
American Airlines, Qatar Airways and Southwest Airlines fly direct from Chicago to San Diego.
As of August 2026, there are 4,437 flights per week flying from Chicago to San Diego.
The cheapest month to fly from Chicago to San Diego is usually September.
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 $303.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to San Diego on Saturday, 12 September 2026.
Yes – the average flight time is 4 hours and 26 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 August, the average temperature is usually around 23°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 Frontier Airlines. And the cheapest airline that flies to McClellan-Palomar Airport is Alaska Airlines.

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

  • Begin your trip planning by checking out the most convenient departure point for your flight from Chicago to San Diego. Explore your options for setting off from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW), two of the city's main airports.

  • When it comes to arriving in San Diego, San Diego International Airport (SAN) is a key hub. McClellan-Palomar Airport (CLD) is another.

  • The average length of a direct Chicago to San Diego flight is 4 hours 20 minutes.

  • San Diego is two hours behind Chicago and follows the UTC-8 timezone.

  • There are 76 weekly services between Chicago O'Hare International Airport (ORD) and San Diego International Airport (SAN). This is the most popular route when booking flights from Chicago to San Diego.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your Chicago to San Diego flight.

  • During popular months like July, it's best to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight when you travel during high season in general.

How to find the cheapest flights from Chicago to San Diego

  • Don't wait until the last moment. You're more likely to find cheap Chicago to San Diego flights if you book in advance. Airlines often have some fantastic early bird deals.

  • If you're willing to be flexible with your trip dates, try using the 'Whole month' tool. It'll give you the cheapest price across every month when searching for your plane ticket from Chicago to San Diego.

  • Locking in a cheap flight from Chicago to San Diego is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when a better deal is available.

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

Flying from Chicago

Chicago O'Hare International Airport (ORD)

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

  • Pick from a variety of airlines that offer direct Chicago to San Diego plane tickets out of ORD. Book your seat with one of these:

  • ORD is around 26 kilometres from central Chicago. If you're ride-sharing, catching a taxi or driving from the centre, it'll take 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the journey time to be around 45 minutes.

  • After a leisurely start to your break? Stay near Chicago O'Hare International Airport. Whether you're catching an early flight from Chicago to San Diego or want to avoid feeling rushed, these hotels are perfect:

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

  • ORD is located at 10000 West O'Hare.

Chicago Midway Airport (MDW)

  • Consider booking your direct flight from Chicago to San Diego departing Chicago Midway Airport (MDW). Nonstop connections from MDW will get you to San Diego International Airport (SAN).

  • Southwest Airlines offers direct Chicago to San Diego plane tickets from MDW. Book your favourite window seat and arrive at your destination in one go.

  • MDW is about 14 kilometres from central Chicago. It'll take you 25 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 30 minutes.

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

  • Chicago Midway Airport has an on-time performance of 76%. This figure gives an insight into how often flights that take off from this airport land on schedule.

  • You'll find MDW at 5700 South Cicero.

Arriving in San Diego

San Diego International Airport (SAN)

  • San Diego International Airport (SAN) is approximately 5 kilometres from central San Diego. If you're catching a taxi or a ride-share, the drive will take around 15 minutes.

  • Travelling to the centre on public transport takes roughly 25 minutes.

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

  • Explore without limits with a San Diego International Airport rental car. Book your wheels from Thrifty, Dollar or Budget and see more of San Diego and beyond.

  • For the best deal, book your vehicle from San Diego International Airport about two weeks in advance of your Chicago to San Diego flight.

  • The street address for SAN is N Harbour Dr.

McClellan-Palomar Airport (CLD)

  • McClellan-Palomar Airport (CLD) is roughly 48 kilometres from the centre of San Diego. After your flight from Chicago to San Diego, it takes approximately 35 minutes to reach the heart of the city in a taxi or ride-share.

  • The journey will take roughly 1 hour 30 minutes on public transport.

  • There are some great places ready to welcome you near CLD. Kick back after your Chicago to San Diego flight at one of these well-located options:

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

  • Typically, the sooner you book, the better the deals and choice of vehicles. Reserve your ride from CLD once your travel dates are set.

Best time to go to San Diego

  • August is the busiest month for flights from Chicago to San Diego. To avoid the crowds, go to San Diego in March.

  • Lock in a Chicago to San Diego ticket departing in August if you're eager to explore the city during its warmest month. Expect temperatures in San Diego to range from 16ºC to 27ºC.

  • Search for cheap flights from Chicago to San Diego in February if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between 8ºC and 22ºC on average.

More about San Diego

Explore more of the United States

  • Los Angeles is just one of the many cities in the United States waiting to be explored after you've experienced San Diego. Around 177 kilometres to the northwest, popular attractions include Hollywood Sign, Universal Studios Hollywood and Hollywood Bowl.

  • Around 483 kilometres east of San Diego, Phoenix is another essential stop in the United States. Experience major highlights starting with Camelback Mountain, Yayoi Kusama Fireflies Infinity Mirror Room and Heard Museum.

More travel options

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 12 days.