San Diego

$79+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAN
Mar 5 — Mar 121
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Find cheap flights from Chicago to San Diego with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago to San Diego are usually found in October or February, booked 48 days in advance, depart on a Saturday or Friday and return on a Thursday

Cheap 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 February 3, 2026.

This Southwest deal was found by Cheapflights users on 2/2. 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.
Sat 2/2811:20 am
MDW
-
SAN
1 stop8h 15m
Southwest
Sat 3/76:00 pm
SAN
-
MDW
1 stop5h 55m
Southwest
Deal found 2/2$160
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:05 am
ORD
-
SAN
2 stops30h 42m
Frontier
Sat 3/76:55 am
SAN
-
ORD
1 stop15h 26m
Frontier
Deal found 2/1$160
This WAYA deal was found by Cheapflights users on 2/1. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:30 pm
ORD
-
SAN
1 stop7h 38m
Multiple Airlines
Sat 3/145:42 pm
SAN
-
ORD
Nonstop4h 17m
Multiple Airlines
Deal found 2/1$161
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/214:29 pm
ORD
-
SAN
2 stops17h 55m
Frontier
Sat 2/2811:41 am
SAN
-
ORD
1 stop9h 36m
Frontier
Deal found 2/1$162
This WAYA deal was found by Cheapflights users on 2/1. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/228:20 am
ORD
-
SAN
Nonstop4h 49m
Multiple Airlines
Thu 2/266:25 am
SAN
-
ORD
1 stop6h 29m
Multiple Airlines
Deal found 2/1$163
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sat 2/2811:20 am
MDW
-
SAN
1 stop8h 15m
Southwest
Wed 3/412:10 pm
SAN
-
MDW
1 stop7h 05m
Southwest
Deal found 2/1$164
This WAYA deal was found by Cheapflights users on 2/1. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:07 pm
ORD
-
SAN
Nonstop4h 45m
Multiple Airlines
Mon 3/99:58 pm
SAN
-
ORD
1 stop6h 10m
Multiple Airlines
Deal found 2/1$164
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:25 am
MDW
-
SAN
2 stops13h 26m
Frontier
Sun 3/18:20 pm
SAN
-
MDW
1 stop25h 34m
Frontier
Deal found 2/1$165
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:43 am
ORD
-
SAN
1 stop8h 42m
Frontier
Mon 4/209:07 pm
SAN
-
ORD
1 stop7h 40m
Frontier
Deal found 2/3$165
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 4/256:25 pm
MDW
-
SAN
1 stop7h 00m
Southwest
Sat 5/210:40 pm
SAN
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/31$166
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:44 pm
ORD
-
SAN
1 stop8h 32m
Frontier
Tue 3/102:08 pm
SAN
-
ORD
1 stop14h 00m
Frontier
Deal found 2/1$166
This Southwest deal was found by Cheapflights users on 2/1. 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.
Tue 3/37:50 pm
MDW
-
SAN
Nonstop4h 30m
Southwest
Thu 3/56:45 am
SAN
-
MDW
Nonstop4h 00m
Southwest
Deal found 2/1$167

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$160
(Southwest)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

October

Average price

$243

Good round-trip deal

$200 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Chicago (CHI)-San Diego flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-San Diego flights.
From Chicago (CHI) to San Diego
One-way flight from Chicago (CHI) to San Diego
Highest demand for flights based on searches. 11% potential increase in price ($38 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in February 2026
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.

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 February 3, 2026.
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

Wed 4/22

2:15 pm-8:39 pm

1 stop8h 24m

San Diego

Wed 4/29

10:30 pm-4:35 am

Nonstop4h 05m

$163

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 3/7

8:55 pm-11:25 pm

Nonstop4h 30m

San Diego

Sat 3/14

10:40 pm-4:35 am

Nonstop3h 55m

$167

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 3/5

3:07 pm-5:52 pm

Nonstop4h 45m

San Diego

Tue 3/10

8:35 am-2:58 pm

Nonstop4h 23m

$167

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 3/11

5:10 pm-7:40 pm

Nonstop4h 30m

San Diego

Fri 3/13

4:45 pm-10:35 pm

Nonstop3h 50m

$167

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 3/8

7:05 am-9:47 am

Nonstop4h 42m

San Diego

Wed 3/11

7:00 am-1:15 pm

Nonstop4h 15m

$167

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 3/9

8:55 pm-11:25 pm

Nonstop4h 30m

San Diego

Wed 3/11

10:40 pm-4:35 am

Nonstop3h 55m

$167

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 2/21

8:40 pm-11:10 pm

Nonstop4h 30m

San Diego

Tue 2/24

6:20 am-3:25 pm

1 stop7h 05m

$168

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 3/13

7:05 am-9:47 am

Nonstop4h 42m

San Diego

Sun 3/15

10:30 pm-4:29 am

Nonstop3h 59m

$177

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 4/6

8:20 pm-10:59 pm

Nonstop4h 39m

San Diego

Fri 4/10

4:49 pm-10:59 pm

Nonstop4h 10m

$177

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sun 5/3

9:10 pm-11:25 pm

Nonstop4h 15m

San Diego

Mon 5/18

10:40 pm-4:35 am

Nonstop3h 55m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 41 results
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Compare providers for flights from Chicago to San Diego

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Diego in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San Diego flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Diego flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Diego flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San Diego flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Diego flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 January 30, 2026.

Booking 48 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, April is the cheapest month in which you can book a flight from Chicago to San Diego (average of $84). Flying from Chicago to San Diego in May is currently the most expensive (average of $177). 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 February 3, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego in the evening. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight at noon.

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 January 31, 2026.

Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday mornings 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 February 3, 2026.

The most flights from CHI to SAN are scheduled on a Friday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Chicago to San Diego?

The best insider tips for Chicago to San Diego flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Diego trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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.

Blane Bachelor

Blane Bachelor

Expert on SAN

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.

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 February 3, 2026.
Read through reviews of airlines operating flights from Chicago to San Diego, such as Alaska Airlines, Southwest, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 21 inbound flights from Chicago per day. 8 airlines have flights to San Diego from Chicago on a regular basis.

  • How long is the flight from Chicago to San Diego?

    For as low as $167, United Airlines can have you in San Diego from Chicago in 4h 30m. Airlines will cover a distance of 1725 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $66. Other airlines that can offer you cheap pricing are Frontier, from $98, and Delta, from $128. Users have found that Spirit Airlines is 77% 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 $43. However, be on the lookout for offers from Frontier and Hawaiian Airlines, 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 United Airlines (74%), Austrian Airlines (71%) or Air Canada (70%) 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 $599, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Chicago O'Hare Intl - San Diego), you can expect to pay $131 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, 16th Street Mall, or Paramount Theatre. Coors Field, 16th Street Mall and Paramount Theatre are located about 18.4 mi, 18.7 mi, and 18.6 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 $46 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, April is the cheapest month in which you can book a flight from Chicago to San Diego (average of $84). Flying from Chicago to San Diego in May is currently the most expensive (average of $177). 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove

Browse thousands of different options on Cheapflights for your next trip

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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 8 airlines flying from Chicago to San Diego

Discover the top 8 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$185FlexibilityNo cancel feeOn-time65%
FrontierCheapest$98Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$297FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$138Average$240FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$142Average$258FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$157Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$297FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$177Average$358FlexibilityNo cancel feeOn-time63%

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