Cheap flights from Chicago (CHI) to San Diego (SAN)

CHI — SAN
Jan 31 — Feb 71

The best prices from Chicago to San Diego are usually found in February or January, booked 40 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

How to find the cheapest flight from Chicago (CHI) to San Diego (SAN)

All the information you need to plan the best CHI to SAN flight in 2023: compare Chicago to San Diego flight prices with the expected peak season, weather and rainfall in San Diego.

CHI - SAN

Price

$305 - $537

SAN

Temperature

57.2 - 71.6 °F

SAN

Rainfall

0 - 2.3 inches

Popular inJulyHigh demand for flights, 22% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 27% potential price drop
Round-trip from$305From Chicago (CHI) to San Diego
One-way from$69One-way flight from Chicago (CHI) to San Diego

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

Flights from Chicago to San Diego are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San Diego.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 41 days in advance, which can save you up to 39% on flights from Chicago to San Diego compared to booking the week you need them. Waiting 41 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $481. For sooner than that we have options available in the next 3 days from $627.

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

Our data shows that February tends to be the cheapest month to fly to San Diego from Chicago. Users have commonly found prices around $419 for the month, but tickets can be as low as $197. Due to multiple factors, prepare for potentially higher prices in July.

When is the cheapest time to fly from Chicago to San Diego (CHI - SAN)?

A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego in the morning. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the afternoon.

Cheap flights from Chicago to San Diego in January, February 2023

The best prices found for CHI to SAN flights for January, February
Feb 27 - Mar 1
MDW

Chicago Midway

SAN

San Diego

1 stop

27h 03m
SAN

San Diego

MDW

Chicago Midway

1 stop

13h 21m
$100

Frontier

Pick Dates

Deal found 1/23

Feb 8 - Feb 15
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 16m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

12h 59m
$110

Spirit Airlines

Pick Dates

Deal found 1/23

Feb 8 - Feb 9
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 16m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

5h 58m
$111

Spirit Airlines

Pick Dates

Deal found 1/25

Chicago to San Diego 2023 flight deals

Cheap flights to San Diego from Chicago found for this year
Feb 27 - Mar 1
MDW

Chicago Midway

SAN

San Diego

1 stop

27h 03m
SAN

San Diego

MDW

Chicago Midway

1 stop

13h 21m
$100

Frontier

Pick Dates

Deal found 1/23

Feb 22 - Feb 28
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

13h 49m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

7h 54m
$107

Spirit Airlines

Pick Dates

Deal found 1/25

Mar 8 - Mar 8
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 41m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

6h 40m
$108

Spirit Airlines

Pick Dates

Deal found 1/23

Cheap Frontier flights from Chicago to San Diego

Feb 27 - Mar 1
MDW

Chicago Midway

SAN

San Diego

1 stop

27h 03m
SAN

San Diego

MDW

Chicago Midway

1 stop

13h 21m
$100

Frontier

Pick Dates

Deal found 1/23

Feb 7 - Feb 10
MDW

Chicago Midway

SAN

San Diego

1 stop

10h 34m
SAN

San Diego

MDW

Chicago Midway

1 stop

14h 46m
$131

Frontier

Pick Dates

Deal found 1/24

Mar 3 - Mar 8
MDW

Chicago Midway

SAN

San Diego

1 stop

27h 23m
SAN

San Diego

MDW

Chicago Midway

1 stop

11h 10m
$134

Frontier

Pick Dates

Deal found 1/23

  • One of the most popular airlines traveling from Chicago to San Diego is Frontier. Flights from Frontier traveling this route typically cost $495.45 RT. This price is typically 20% cheaper than other airlines that offer Chicago to San Diego flights. When booking this route, the cheapest RT price found was $200. Chicago O'Hare Intl Airport is the most common Chicago airport to take off from when flying to San Diego. San Diego Airport is the most popular arrival airport in San Diego. When flying from Chicago to San Diego, Frontier flights are 29% more popular than any other airline flying that same route.

Cheap Spirit Airlines flights from Chicago to San Diego

Mar 8 - Mar 8
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 41m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

6h 40m
$108

Spirit Airlines

Pick Dates

Deal found 1/23

Feb 8 - Feb 15
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 16m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

12h 59m
$110

Spirit Airlines

Pick Dates

Deal found 1/23

Feb 8 - Feb 9
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 16m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

5h 58m
$111

Spirit Airlines

Pick Dates

Deal found 1/25

  • If you’re traveling from Chicago to San Diego, one of the more common airlines traveling that route is Spirit Airlines. Chicago to San Diego flights are typically 21% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $506.86 RT. The cheapest Spirit Airlines flight found for this route was $256. When traveling from Chicago to San Diego on Spirit Airlines, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is San Diego Airport. When flying from Chicago to San Diego, Spirit Airlines flights are 23% more popular than any other airline flying that same route.

Non-stop flights to San Diego from Chicago

Save time with Chicago to San Diego direct flight deals
Mar 7 - Mar 14
ORD

Chicago O'Hare Intl

SAN

San Diego

Nonstop

4h 25m
SAN

San Diego

ORD

Chicago O'Hare Intl

Nonstop

3h 55m
$318

United Airlines

Pick Dates

Deal found 1/23

Feb 25 - Feb 28
ORD

Chicago O'Hare Intl

SAN

San Diego

Nonstop

4h 30m
SAN

San Diego

ORD

Chicago O'Hare Intl

Nonstop

3h 57m
$328

United Airlines

Pick Dates

Deal found 1/26

Feb 27 - Mar 1
ORD

Chicago O'Hare Intl

SAN

San Diego

Nonstop

4h 27m
SAN

San Diego

ORD

Chicago O'Hare Intl

Nonstop

4h 02m
$338

American Airlines

Pick Dates

Deal found 1/23

Last minute flights from Chicago to San Diego

Late deals on return flights to San Diego from Chicago, departing today and this week
Feb 1 - Feb 8
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

11h 05m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

7h 54m
$124

Spirit Airlines

Pick Dates

Deal found 1/24

Feb 1 - Feb 8
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

7h 34m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

12h 59m
$126

Multiple Airlines

Pick Dates

Deal found 1/24

Feb 1 - Mar 14
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

13h 56m
SAN

San Diego

ORD

Chicago O'Hare Intl

1 stop

14h 50m
$127

Spirit Airlines

Pick Dates

Deal found 1/23

One-way flights to San Diego from Chicago

The cheapest one-way flights from Chicago to San Diego
Feb 28
MDW

Chicago Midway

SAN

San Diego

1 stop

16h 59m
$42

Frontier

Pick Dates

Deal found 1/23

Feb 27
MDW

Chicago Midway

SAN

San Diego

1 stop

27h 03m
$54

Frontier

Pick Dates

Deal found 1/23

Feb 28
ORD

Chicago O'Hare Intl

SAN

San Diego

1 stop

11h 16m
$54

Frontier

Pick Dates

Deal found 1/25

Reviews of Airlines Servicing San Diego

Spirit Airlines
6.9
Okay
707 reviews

Boarding

7.2

Crew

7.4

Comfort

6.4

Entertainment

5.6

Food

5.6

Overall

6.9

Reviews

1 / 10

I had entered my TSA number, confirmed with the telephone representative that it was on the ticket, and it did not print on my ticket. I had to go through the security line twice. I was charged $74 to check in a bag, and $60 for a carry-on. For round-trip, this adds $260 above the cost of the ticket. For a 1.5 hour flight. I will never fly Spirit Airlines again.

Spirit Airlines
6.9
Okay
707 reviews
Spirit Airlines
6.9
Okay
707 reviews

Boarding

7.2

Crew

7.4

Comfort

6.4

Entertainment

5.6

Food

5.6

Overall

6.9

Reviews

1 / 10

I had entered my TSA number, confirmed with the telephone representative that it was on the ticket, and it did not print on my ticket. I had to go through the security line twice. I was charged $74 to check in a bag, and $60 for a carry-on. For round-trip, this adds $260 above the cost of the ticket. For a 1.5 hour flight. I will never fly Spirit Airlines again.

Frontier
6.1
Okay
536 reviews
Spirit Airlines
6.9
Okay
707 reviews

Boarding

7.2

Crew

7.4

Comfort

6.4

Entertainment

5.6

Food

5.6

Overall

6.9

Reviews

1 / 10

I had entered my TSA number, confirmed with the telephone representative that it was on the ticket, and it did not print on my ticket. I had to go through the security line twice. I was charged $74 to check in a bag, and $60 for a carry-on. For round-trip, this adds $260 above the cost of the ticket. For a 1.5 hour flight. I will never fly Spirit Airlines again.

Related info for your journey

Useful info, stats and facts about Chicago to San Diego flights.

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 26 inbound flights from Chicago per day. 11 airlines have flights to San Diego from Chicago on a regular basis.

Which airlines flying from Chicago to San Diego have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Spirit Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to San Diego for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to San Diego for under $100. The cheapest flight booked recently is on Frontier for just $100, but on average you can expect to pay $116.

Are there nonstop flights from Chicago to San Diego for under $400 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San Diego under $400. A good price for a nonstop flight from Chicago to San Diego is less than $363.

Are there last-minute flights available from Chicago to San Diego for under $200?

There are currently 20+ open flights from Chicago to San Diego within the next 7 days for less than $200.

What days are nonstop flights available from Chicago to San Diego?

Days when nonstop flights are available for this flight are: Friday.

How many flights depart from Chicago to San Diego on average per day?

On average 7 flights depart from Chicago to San Diego per day.
Afternoon (Noon - 6pm) - 43% of flight departures
Evening (6pm - Midnight) - 57% of flight departures

How long is the flight from Chicago to San Diego?

For as low as $100, Frontier can have you in San Diego from Chicago in 7h 41m. Airlines will cover a distance of 1729 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 $100. Another airline that can offer you cheap pricing is Spirit Airlines. Users have found that Frontier is 76% cheaper than the other options available to this destination.

What are the most popular airlines that fly from Chicago to San Diego?

Consider Undisclosed Carrier, American Airlines or Alaska Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to San Diego.

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 LOT (100%), Austrian Airlines (84%) or Brussels Airlines (84%) 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 $835, our data shows the cheapest flight currently is $66. When looking at the most popular route, (Chicago O'Hare Intl - San Diego), you can expect to pay $109 for that flight.

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

The chart below displays the airlines Cheapflights users traveling from Chicago to San Diego choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$12Average$22FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$115Average$248FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
FrontierCheapest$117Average$242FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
DeltaCheapest$168Average$556FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$197Average$481FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$200Average$495FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
United AirlinesCheapest$256Average$507FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chicago to San Diego

See what time of day planes typically take off from Chicago to San Diego
7%of flight departuresEarly morningMidnight to 6 am
24%of flight departuresMorning6 am to noon
47%of flight departuresAfternoonNoon to 6 pm
22%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to San Diego

See how many times per day planes take to the skies headed from Chicago to San Diego
Sunday24daily flights
Monday34daily flights
Tuesday29daily flights
Wednesday33daily flights
Thursday29daily flights
Friday30daily flights
Saturday3daily flights
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