San Diego

$93+ Cheap flights from Chicago (CHI) to San Diego (SAN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAN
juin 17 — juin 241
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Cheapflights Tip: The best prices from Chicago to San Diego are usually found in June or August, booked 83 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to San Diego

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Diego (SAN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated juin 12, 2025.

Round-trip from

$176
(Cheapflightsfares)

One-way from

$93
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$301

Good round-trip deal

$221 or less

Good one-way deal

$128 or less
From Chicago (CHI) to San Diego
One-way flight from Chicago (CHI) to San Diego
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in June 2025
Price to beat on a round-trip flight from Chicago (CHI) to San Diego.
Price to beat on a one-way flight from Chicago (CHI) to San Diego.

Find flight deals from Chicago to San Diego

Cheapest flights from Chicago to San Diego
Explore the most affordable flight options available from Chicago to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juin 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 6/181:56 pmORD - SAN
Nonstop4h 12mFrontier
sam. 6/214:53 pmSAN - ORD
Nonstop4h 03mFrontier
Deal found 6/10$176
This FlightHub deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/2411:50 amORD - SAN
1 stop13h 39mSpirit Airlines
lun. 6/305:50 pmSAN - ORD
2 stops13h 48mSpirit Airlines
Deal found 6/10$177
This Priceline deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/241:56 pmORD - SAN
Nonstop4h 12mMultiple Airlines
lun. 6/307:31 pmSAN - ORD
1 stop8h 41mMultiple Airlines
Deal found 6/10$178
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/228:50 pmMDW - SAN
Nonstop4h 15mSouthwest
mar. 8/268:10 amSAN - MDW
Nonstop4h 00mSouthwest
Deal found 6/10$186
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/229:13 amORD - SAN
Nonstop4h 27mUnited Airlines
mar. 8/262:11 pmSAN - ORD
Nonstop4h 14mUnited Airlines
Deal found 6/10$186
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/151:03 pmORD - SAN
1 stop9h 51mAlaska Airlines
lun. 8/187:00 amSAN - ORD
1 stop14h 39mAlaska Airlines
Deal found 6/10$230
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 7/57:14 amORD - SAN
Nonstop4h 14mAmerican Airlines
sam. 7/1210:45 pmSAN - ORD
Nonstop4h 11mAmerican Airlines
Deal found 6/11$239
This Hawaiian Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/93:20 pmORD - SAN
1 stop9h 42mHawaiian Airlines
lun. 10/135:19 pmSAN - ORD
Nonstop4h 40mHawaiian Airlines
Deal found 6/12$247
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/231:08 pmMDW - SAN
1 stop6h 53mDelta
mar. 8/2610:30 pmSAN - MDW
1 stop8h 46mDelta
Deal found 6/10$257
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/27:00 amORD - SAN
1 stop7h 20mDelta
mar. 8/1210:40 pmSAN - ORD
1 stop7h 24mDelta
Deal found 6/11$257
This Booking.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/142:44 pmMDW - SAN
1 stop21h 08mFrontier
dim. 8/176:25 amSAN - MDW
1 stop27h 16mFrontier
Deal found 6/12$260
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 8/207:30 amORD - SAN
2 stops9h 50mSouthwest
dim. 8/246:20 amSAN - ORD
1 stop7h 00mSouthwest
Deal found 6/10$262

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to San Diego that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated juin 12, 2025.
Use the filters below to find and compare flights from Chicago to San Diego that are best for you.

Fly from

Chicago

Fly to

San Diego

Route

Depart

Return

Price

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

mer. 6/18

1:56 pm-4:08 pm

Nonstop4h 12m

San Diego

sam. 6/21

4:53 pm-10:56 pm

Nonstop4h 03m

$176

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

mar. 6/24

11:50 am-11:29 pm

1 stop13h 39m

San Diego

lun. 6/30

5:50 pm-9:38 am

2 stops13h 48m

$177

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

mar. 6/24

1:56 pm-4:08 pm

Nonstop4h 12m

San Diego

lun. 6/30

7:31 pm-6:12 am

1 stop8h 41m

$178

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

ven. 8/22

8:50 pm-11:05 pm

Nonstop4h 15m

San Diego

mar. 8/26

8:10 am-2:10 pm

Nonstop4h 00m

$186

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

ven. 8/22

9:13 am-11:40 am

Nonstop4h 27m

San Diego

mar. 8/26

2:11 pm-8:25 pm

Nonstop4h 14m

$186

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

dim. 8/17

9:00 pm-11:23 pm

Nonstop4h 23m

San Diego

sam. 8/23

1:08 pm-7:25 pm

Nonstop4h 17m

$199

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

ven. 8/15

1:03 pm-8:54 pm

1 stop9h 51m

San Diego

lun. 8/18

7:00 am-11:39 pm

1 stop14h 39m

$230

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

sam. 8/23

1:08 pm-6:01 pm

1 stop6h 53m

San Diego

mar. 8/26

10:30 pm-9:16 am

1 stop8h 46m

$257

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

sam. 8/2

7:00 am-12:20 pm

1 stop7h 20m

San Diego

lun. 8/11

10:30 pm-10:04 am

1 stop9h 34m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

jeu. 8/14

2:44 pm-9:52 am

1 stop21h 08m

San Diego

dim. 8/17

6:25 am-11:41 am

1 stop27h 16m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 25 results
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The best insider tips for Chicago to San Diego flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Diego trip
Airlines
United Airlines

Basic Economy on United allows a personal item only, no carry-on bags without exceptions.


United Economy Plus offers extra legroom seats at the front of the economy cabin.

Southwest

Southwest allows two free checked bags, including oversized items like skis or golf clubs.


Southwest offers free in-flight messaging and high-speed Wi-Fi for a fee.

Airports
ORD

For a quick snack, grab Garrett Popcorn near gate B8, a Chicago favorite, perfect before your flight.

Read more about ORDby Ramsey Qubein
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
SAN

Take the free San Diego Flyer shuttle between SAN and the Old Town Transit Center for a convenient and cost-effective option.

Read more about SANby Blane Bachelor
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Blane Bachelor

Blane Bachelor

Expert on SAN

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Best time to book a flight from Chicago to San Diego

Have a flexible travel schedule? Discover the best time to fly to San Diego from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Diego

How far ahead should I book a flight from Chicago to San Diego?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Diego. Price data was last updated on June 9, 2025.

Booking 83 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Diego. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to San Diego?

Currently, August is the cheapest month in which you can book a flight from Chicago to San Diego (average of $286). Flying from Chicago to San Diego in March is currently the most expensive (average of $366). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SAN?

Find hourly flight availability from Chicago to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juin 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego at noon. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Chicago to San Diego?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Diego. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to San Diego

Explore weekly flight availability from Chicago to San Diego. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated juin 12, 2025.

The most flights from CHI to SAN are scheduled on a Thursday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 on average).

Rainfall in San Diego by month

Plan your trip to San Diego by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Diego ranges from 0.0 - 2.3 inches per month. February is typically the wettest month, when rainfall can reach 2.3 in. July is typically the driest time to visit San Diego when rainfall is around 0.0 in.

Temperature in San Diego by month

Plan your trip to San Diego by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Diego, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 57.2 F).

Reviews of airlines servicing San Diego

Get insights into the airlines that provide service to San Diego. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Diego. Reviews last updated juin 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Chicago to San Diego by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
8.0
Very good

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Diego. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to San Diego from Chicago?

    For a flight from Chicago to San Diego, you will be flying into San Diego. San Diego (SAN) is just 2.6 mi from the center of the city. San Diego is the only San Diego airport and it handles 41 inbound flights from Chicago per day. 7 airlines have flights to San Diego from Chicago on a regular basis.

  • What are the cheapest airlines flying from Chicago to San Diego round-trip?

    Cheapflights users have booked flights from Chicago to San Diego round-trip from $176. Other airlines that can offer you cheap pricing are Spirit Airlines, from $177, and Southwest, from $186. Users have found that Frontier is 54% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to San Diego one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $93. However, be on the lookout for offers from Alaska Airlines and Frontier, as they are both options that can get you from Chicago to San Diego for a low price.

  • What are the most reliable airlines from Chicago to San Diego?

    No one likes to see their flight delayed. When booking a flight from Chicago to San Diego consider choosing Japan Airlines (96%), Austrian Airlines (90%) or Air Canada (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to San Diego?

    While on average a flight from Chicago to San Diego is generally $658, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Chicago O'Hare Intl - San Diego), you can expect to pay $94 for that flight.

  • Where are the most common layover locations when flying from Chicago to San Diego?

  • What are some popular things to do or see while on a layover in Denver?

    If you're on a layover in Denver and looking for things to do, consider visiting Coors Field, Paramount Theatre, or Larimer Square. Coors Field, Paramount Theatre and Larimer Square are located about 18.4 mi, 18.6 mi, and 18.9 mi, respectively from Denver Intl if you are interested in checking them out. Those looking to explore during their layover in Denver can rent a car from Denver Intl for about $54 per day.

  • What are some popular points of interest to see during a layover in Las Vegas?

    Fremont Street Experience, The Colosseum at Caesars Palace, and Fountains of Bellagio are the most popular attractions in Las Vegas if you're in need of something to do during your layover. Fremont Street Experience, The Colosseum at Caesars Palace, and Fountains of Bellagio can be visited by traveling about 5.9 mi, 2.6 mi, and 2.3 mi respectively from Las Vegas Harry Reid Intl. Those landing in Las Vegas looking to spend some time exploring during their layover can rent a car for about $55 per day.

  • Where are the least popular layover locations for Chicago to San Diego flights?

  • Can I find deals for flights from Chicago to San Diego that include hotel bookings?

    Yes. In addition to deals on Chicago to San Diego flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San Diego?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Diego.

  • Can I find deals for business class flights from Chicago to San Diego?

    Yes. Cheapflights offers flight deals from Chicago to San Diego by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San Diego?

    Currently, August is the cheapest month in which you can book a flight from Chicago to San Diego (average of $286). Flying from Chicago to San Diego in March is currently the most expensive (average of $366). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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Alternative routes for Chicago to San Diego

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Chicago to San Diego

Discover the top 7 airlines that operate flights from Chicago to San Diego. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$97Average$224FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$203FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$216Average$409FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$220Average$469FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$338FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$246Average$566FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$246Average$473FlexibilityNo cancel feeOn-time69%

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