San Diego

$81+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAN
ene. 21 — ene. 281
We work with more than 300 partners to bring you better travel deals

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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago to San Diego are usually found in April or May, booked 65 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 enero 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Kiwi.com)

One-way from

$81
(Trip.com)

Popular in

March

Cheapest in

April

Average price

$456
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
High demand for flights, 1% potential price rise
Best time to find cheap flights, 1% potential price drop
Average for round-trip flights in January 2025

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 enero 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
sáb. 2/158:44 pmMDW - SAN
1 stop18h 44mFrontier
vie. 2/216:25 amSAN - MDW
1 stop15h 52mFrontier
Deal found 1/15$148
This Cheapflightsfares deal was found by Cheapflights users on 1/15. 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.
jue. 5/83:31 pmORD - SAN
1 stop6h 18mFrontier
jue. 5/156:25 amSAN - ORD
1 stop6h 01mFrontier
Deal found 1/15$148
This FlightHub deal was found by Cheapflights users on 1/15. 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.
lun. 1/2710:47 pmORD - SAN
1 stop16h 08mSpirit Airlines
mié. 2/54:21 pmSAN - ORD
1 stop11h 10mSpirit Airlines
Deal found 1/15$149
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
vie. 1/318:46 pmORD - SAN
1 stop12h 59mMultiple Airlines
mar. 2/47:26 pmSAN - ORD
1 stop8h 05mMultiple Airlines
Deal found 1/15$154
This Kissandfly.com deal was found by Cheapflights users on 1/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/48:15 amMDW - SAN
2 stops14h 04mMultiple Airlines
mié. 2/126:15 amSAN - MDW
2 stops16h 02mMultiple Airlines
Deal found 1/16$251
This Delta deal was found by Cheapflights users on 1/15. 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.
jue. 2/62:25 pmORD - SAN
1 stop9h 54mDelta
dom. 2/96:25 amSAN - ORD
1 stop7h 05mDelta
Deal found 1/15$276
This Delta deal was found by Cheapflights users on 1/15. 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.
vie. 2/712:44 pmMDW - SAN
1 stop8h 07mDelta
sáb. 2/86:15 amSAN - MDW
1 stop6h 38mDelta
Deal found 1/15$279
This Southwest deal was found by Cheapflights users on 1/16. 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.
sáb. 2/158:45 pmMDW - SAN
Nonstop4h 30mSouthwest
sáb. 2/226:20 amSAN - MDW
Nonstop3h 50mSouthwest
Deal found 1/16$341

Find flights from Chicago to San Diego within your budget

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 enero 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

sáb. 2/15

8:44 pm-1:28 pm

1 stop18h 44m

San Diego

vie. 2/21

6:25 am-12:17 am

1 stop15h 52m

$148

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

jue. 5/8

3:31 pm-7:49 pm

1 stop6h 18m

San Diego

jue. 5/15

6:25 am-2:26 pm

1 stop6h 01m

$148

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

lun. 1/27

10:47 pm-12:55 pm

1 stop16h 08m

San Diego

mié. 2/5

4:21 pm-5:31 am

1 stop11h 10m

$149

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

vie. 1/31

8:46 pm-7:45 am

1 stop12h 59m

San Diego

mar. 2/4

7:26 pm-5:31 am

1 stop8h 05m

$154

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

mar. 2/4

8:15 am-8:19 pm

2 stops14h 04m

San Diego

mié. 2/12

6:15 am-12:17 am

2 stops16h 02m

$251

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

jue. 2/6

7:15 am-5:59 pm

1 stop12h 44m

San Diego

mar. 2/11

11:20 am-12:11 am

1 stop10h 51m

$264

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

vie. 2/7

12:44 pm-6:51 pm

1 stop8h 07m

San Diego

sáb. 2/8

6:15 am-2:53 pm

1 stop6h 38m

$279

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

sáb. 2/15

8:45 pm-11:15 pm

Nonstop4h 30m

San Diego

sáb. 2/22

4:55 pm-10:45 pm

Nonstop3h 50m

$341

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

jue. 1/30

7:25 am-11:52 pm

1 stop18h 27m

$81

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

vie. 2/28

9:56 pm-9:01 am

1 stop13h 05m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 22 results
1
2
3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice 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.

Travel insights for flights from Chicago to San Diego

Get recent, data-driven insights about flights from Chicago to San Diego including ideal travel times, pricing trends, and more.

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 10, 2025.

Booking 65 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 enero 16, 2025.

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 13% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon 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 enero 16, 2025.

The most flights from CHI to SAN are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 enero 16, 2025.
Get a feel of what it's like to fly with Spirit Airlines, Delta and Frontier 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.
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

8.1
Very good
4,659 reviews
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

8.0
Very good
9,681 reviews
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

8.0
Very good
8,511 reviews
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

7.4
Good
8,965 reviews
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

7.2
Good
10,000 reviews
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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. 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 $148. Other airlines that can offer you cheap pricing are Spirit Airlines, from $149, and Delta, from $276. Users have found that Frontier is 64% 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 Frontier, with whom users have recently found tickets for as low as $81. However, be on the lookout for offers from Spirit Airlines and Alaska 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 Brussels Airlines (82%), Air Canada (77%) or United Airlines (77%) 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 $686, our data shows the cheapest flight currently is $155. When looking at the most popular route, (Chicago O'Hare Intl - San Diego), you can expect to pay $107 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 Las Vegas?

    If you're on a layover in Las Vegas and looking for things to do, consider visiting Fremont Street Experience, Colosseum at Caesars Palace, or Stratosphere Tower. Fremont Street Experience, Colosseum at Caesars Palace and Stratosphere Tower are located about 5.9 mi, 2.6 mi, and 4.3 mi, respectively from Las Vegas Harry Reid Intl if you are interested in checking them out. Those looking to explore during their layover in Las Vegas can rent a car from Las Vegas Harry Reid Intl for about $54 per day.

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

    Coors Field, 16th Street Mall, and Paramount Theatre are the most popular attractions in Denver if you're in need of something to do during your layover. Coors Field, 16th Street Mall, and Paramount Theatre can be visited by traveling about 18.4 mi, 18.7 mi, and 18.6 mi respectively from Denver Intl. Those landing in Denver looking to spend some time exploring during their layover can rent a car for about $52 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?

Book flights to Chicago if you plan to visit one of these locations
El Cajon
Chula Vista
Lemon Grove
National City
Imperial Beach
La Mesa
Alpine
Poway
Santee
Coronado
Borrego Springs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 enero 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$103Average$220FlexibilityNo cancel feeOn-time65%
FrontierCheapest$106Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$201Average$483FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$426FlexibilityNo cancel feeOn-time71%
DeltaCheapest$235Average$401FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$246Average$476FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$399Average$698FlexibilityNo cancel feeOn-time75%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.