San Diego

$94+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAN
Feb 25 — Mar 41
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The best prices from Chicago to San Diego are usually found in April or May, booked 58 days in advance, depart on a Tuesday or Wednesday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$139
(Mytrip)

One-way from

$94
(Cheapflightsfares)

Popular in

March

Cheapest in

April

Average price

$386

Good round-trip deal

$387 or less

Good one-way deal

$215 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
High demand for flights, 0% potential price rise
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/22:34 pmORD - SAN
1 stop11h 17mSpirit Airlines
Tue 4/83:29 pmSAN - ORD
2 stops13h 04mSpirit Airlines
Deal found 2/19$139
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/106:40 amMDW - SAN
1 stop19h 40mFrontier
Thu 3/139:46 pmSAN - MDW
1 stop5h 45mFrontier
Deal found 2/19$140
This Frontier deal was found by Cheapflights users on 2/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/256:50 amORD - SAN
1 stop6h 58mFrontier
Sat 3/112:05 pmSAN - ORD
1 stop10h 56mFrontier
Deal found 2/18$140
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/286:30 amORD - SAN
1 stop7h 18mMultiple Airlines
Tue 4/18:07 pmSAN - ORD
1 stop8h 35mMultiple Airlines
Deal found 2/19$144
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 3/126:15 amORD - SAN
2 stops10h 21mDelta
Sat 3/1511:05 amSAN - ORD
1 stop10h 48mDelta
Deal found 2/20$288
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 3/181:16 pmMDW - SAN
1 stop9h 22mDelta
Tue 3/256:20 amSAN - MDW
1 stop5h 55mDelta
Deal found 2/19$299
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/78:40 amMDW - SAN
3 stops17h 04mMultiple Airlines
Sun 3/97:50 amSAN - MDW
1 stop24h 19mMultiple Airlines
Deal found 2/19$368
This Southwest deal was found by Cheapflights users on 2/18. 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.
Thu 5/811:55 amMDW - SAN
Nonstop4h 15mSouthwest
Mon 5/125:55 pmSAN - MDW
Nonstop4h 00mSouthwest
Deal found 2/18$383

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 February 20, 2025.

Fly from

Chicago

Fly to

San Diego

Route

Depart

Return

Price

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 4/2

2:34 pm-11:51 pm

1 stop11h 17m

San Diego

Tue 4/8

3:29 pm-6:33 am

2 stops13h 04m

$139

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 3/10

6:40 am-12:20 am

1 stop19h 40m

San Diego

Thu 3/13

9:46 pm-5:31 am

1 stop5h 45m

$140

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 3/10

7:59 pm-7:17 pm

1 stop25h 18m

San Diego

Thu 3/13

12:38 pm-12:23 am

1 stop9h 45m

$140

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 3/28

6:30 am-11:48 am

1 stop7h 18m

San Diego

Tue 4/1

8:07 pm-6:42 am

1 stop8h 35m

$144

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 3/12

6:15 am-2:36 pm

2 stops10h 21m

San Diego

Sat 3/15

11:05 am-11:53 pm

1 stop10h 48m

$288

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 3/18

1:16 pm-8:38 pm

1 stop9h 22m

San Diego

Tue 3/25

6:20 am-2:15 pm

1 stop5h 55m

$299

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 3/7

8:40 am-11:44 pm

3 stops17h 04m

San Diego

Sun 3/9

7:50 am-10:09 am

1 stop24h 19m

$368

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 5/8

11:55 am-2:10 pm

Nonstop4h 15m

San Diego

Mon 5/12

5:55 pm-11:55 pm

Nonstop4h 00m

$383

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 3/7

6:40 am-11:48 am

1 stop7h 08m

$94

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 4/25

5:25 pm-12:14 am

1 stop8h 49m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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 February.
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
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust 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 February 14, 2025.

Booking 58 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 February 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego in the afternoon. If you’re flexible enough to do this you can expect to save up to 9% 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 February 16, 2025.

Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday 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 February 20, 2025.

The most flights from CHI to SAN are scheduled on a Thursday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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.

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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.

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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.

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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.

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

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 24 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 $139. Other airlines that can offer you cheap pricing are Frontier, from $140, and Delta, from $288. Users have found that Spirit Airlines is 66% 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 $94. However, be on the lookout for offers from Spirit Airlines and Delta, 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 (83%), United Airlines (79%) or Air Canada (79%) 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 $762, our data shows the cheapest flight currently is $163. When looking at the most popular route, (Chicago O'Hare Intl - San Diego), you can expect to pay $81 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 $47 per day.

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

    Fremont Street Experience, Colosseum at Caesars Palace, and Stratosphere Tower are the most popular attractions in Las Vegas if you're in need of something to do during your layover. Fremont Street Experience, Colosseum at Caesars Palace, and Stratosphere Tower can be visited by traveling about 5.9 mi, 2.6 mi, and 4.3 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 $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, 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
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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$103Average$221FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$188FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$421FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$218Average$477FlexibilityNo cancel feeOn-time63%
DeltaCheapest$237Average$413FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$246Average$476FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$403Average$721FlexibilityNo cancel feeOn-time75%
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