What is the cheapest airline that flies from Chicago to San Diego?

Southwest, United Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to San Diego

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

151 flights are operational weekly from Chicago to San Diego as of December 2025. The most popular departure day for this route is Thu, with 26% of flights per week taking off on this day.

What airlines fly to San Diego?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to San Diego from Chicago according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 8 different airlines that fly to San Diego on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Chicago and San Diego is 21 per day as of December 2025. The most frequent departure time is 6:00PM, with 50% of daily flights leaving in the evening.

When did momondo last update prices for flights from Chicago to San Diego Airport?

Prices for flights from Chicago to San Diego Airport refresh daily.

How many operators does momondo search for flights from Chicago to San Diego Airport?

As of December 2025, there are 8 operators available to choose from for flights from Chicago to San Diego Airport.

How old do you have to be to fly from Chicago to San Diego Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to San Diego Airport.

What documentation or ID do you need to fly to San Diego Airport?

The travel and health documents you'll need for your trip to San Diego Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Diego Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$79 Cheap Flights from Chicago to San Diego in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and San Diego?

Prices are currently low for flights on this route. Typical prices usually range from $177 to $402. The lowest price recently found on this route was $157.

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Find the cheapest flights from Chicago to San Diego

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:55 pm - 11:25 pm

MDW

SAN

4h 30mnonstop

10:40 pm - 4:35 am

SAN

MDW

3h 55mnonstop

$157Southwest

Sat, Mar 14 - Wed, Mar 18

1:00 pm - 3:36 pm

ORD

SAN

4h 36mnonstop

7:00 am - 1:13 pm

SAN

ORD

4h 13mnonstop

$157United Airlines

Sat, Jan 17 - Wed, Jan 21

7:50 pm - 10:26 pm

ORD

SAN

4h 36mnonstop

1:58 pm - 8:15 pm

SAN

ORD

4h 17mnonstop

$158American Airlines

Sat, Jan 10 - Tue, Jan 13

12:53 pm - 11:28 am

ORD

SAN

24h 35m1 stop

9:50 am - 10:30 pm

SAN

ORD

10h 40m1 stop

$160Frontier

Fri, Feb 20 - Mon, Feb 23

11:05 am - 12:24 am

MDW

SAN

15h 19m1 stop

6:54 am - 5:20 pm

SAN

MDW

8h 26m1 stop

$161Frontier

Thu, Jan 15 - Sun, Jan 18

4:16 pm - 12:08 am

ORD

SAN

9h 52m1 stop

4:12 pm - 2:30 pm

SAN

ORD

20h 18m1 stop

$161Frontier

Thu, Feb 19 - Sun, Feb 22

7:25 pm - 8:24 pm

MDW

SAN

26h 59m1 stop

9:45 am - 3:19 pm

SAN

MDW

27h 34m1 stop

$162Frontier

Mon, Feb 23 - Fri, Feb 27

12:56 pm - 7:25 pm

ORD

SAN

8h 29m1 stop

2:00 pm - 10:51 am

SAN

ORD

18h 51m2 stops

$162Frontier

Sun, Feb 22 - Mon, Mar 2

3:44 pm - 6:26 pm

ORD

SAN

4h 42mnonstop

8:00 am - 2:29 pm

SAN

ORD

4h 29mnonstop

$166Alaska Airlines

Sun, Jan 18 - Thu, Jan 22

3:07 pm - 5:52 pm

ORD

SAN

4h 45mnonstop

5:42 pm - 11:59 pm

SAN

ORD

4h 17mnonstop

$167Alaska Airlines

Fri, Feb 27 - Wed, Mar 4

American Airlines flights from Chicago to San Diego

Our best American Airlines deals on Chicago to San Diego flight tickets

American Airlines

Jan 10

ORD7:50 pmChicago O'Hare Intl

4h 36m

SAN10:26 pmSan Diego

Jan 13

SAN1:58 pmSan Diego

4h 17m

ORD8:15 pmChicago O'Hare Intl

$158

Find similar

American Airlines

Dec 22

ORD11:43 amChicago O'Hare Intl

4h 30m

SAN2:13 pmSan Diego

Dec 25

SAN6:15 amSan Diego

4h 25m

ORD12:40 pmChicago O'Hare Intl

$393

Find similar

American Airlines

Dec 22

ORD1:40 pmChicago O'Hare Intl

6h 57m

1 stop

SAN6:37 pmSan Diego

Dec 25

SAN6:15 amSan Diego

4h 25m

ORD12:40 pmChicago O'Hare Intl

$403

Find similar

Southwest flights from Chicago to San Diego

Our best Southwest deals on Chicago to San Diego flight tickets

Southwest

Jan 17

MDW7:40 pmChicago Midway

4h 30m

SAN10:10 pmSan Diego

Jan 21

SAN6:25 amSan Diego

4h 00m

MDW12:25 pmChicago Midway

$157

Find similar

Southwest

Jan 10

MDW8:25 amChicago Midway

4h 40m

SAN11:05 amSan Diego

Jan 13

SAN11:40 amSan Diego

5h 25m

1 stop

MDW7:05 pmChicago Midway

$167

Find similar

Southwest

Jan 27

MDW7:50 pmChicago Midway

4h 30m

SAN10:20 pmSan Diego

Jan 31

SAN7:25 amSan Diego

3h 55m

MDW1:20 pmChicago Midway

$177

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 3/14

8:55 pm-11:25 pm

Nonstop4h 30m

San Diego

Wed 3/18

10:40 pm-4:35 am

Nonstop3h 55m

$157

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 1/17

1:00 pm-3:36 pm

Nonstop4h 36m

San Diego

Wed 1/21

7:00 am-1:13 pm

Nonstop4h 13m

$157

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 1/10

7:50 pm-10:26 pm

Nonstop4h 36m

San Diego

Tue 1/13

1:58 pm-8:15 pm

Nonstop4h 17m

$158

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 2/20

12:53 pm-11:28 am

1 stop24h 35m

San Diego

Mon 2/23

9:50 am-10:30 pm

1 stop10h 40m

$160

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 1/15

11:05 am-12:24 am

1 stop15h 19m

San Diego

Sun 1/18

6:54 am-5:20 pm

1 stop8h 26m

$161

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 2/19

4:16 pm-12:08 am

1 stop9h 52m

San Diego

Sun 2/22

4:12 pm-2:30 pm

1 stop20h 18m

$161

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 2/23

7:25 pm-8:24 pm

1 stop26h 59m

San Diego

Fri 2/27

9:45 am-3:19 pm

1 stop27h 34m

$162

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 2/22

12:56 pm-7:25 pm

1 stop8h 29m

San Diego

Mon 3/2

2:00 pm-10:51 am

2 stops18h 51m

$162

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 1/18

3:44 pm-6:26 pm

Nonstop4h 42m

San Diego

Thu 1/22

8:00 am-2:29 pm

Nonstop4h 29m

$166

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 2/27

3:07 pm-5:52 pm

Nonstop4h 45m

San Diego

Wed 3/4

5:42 pm-11:59 pm

Nonstop4h 17m

$167

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to San Diego

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Chicago and San Diego?

What is the cheapest month to fly to San Diego?

If you are unable to visit San Diego during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $244.

What is the cheapest day to depart on your flight to San Diego?

The cheapest day to depart from Chicago to San Diego is on a Friday. Travelers who choose to depart for San Diego on a Friday will often find tickets for as low as $294. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $379. These prices are subject to change though, so be sure to set up a Price Alert for flights to San Diego.

What is the cheapest time of day to depart on your flight to San Diego?

The cheapest time of day to fly to San Diego is at noon when flights can be purchased for as low as $266. Flights in the afternoon are often more expensive with an average ticket price of $374.

What is the cheapest Chicago to San Diego flight route?

Fly from Chicago O'Hare Intl to San Diego for the best Chicago - San Diego flight prices

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

You are more likely to see cheaper flights to San Diego from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $309 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Diego from Chicago for as low as $251 on momondo.

What cabin class options are available on Chicago to San Diego flights?

There are 4 cabin classes available to choose from on Chicago to San Diego flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San Diego flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago to San Diego flight.

How have Chicago to San Diego flight prices changed over time?

As of December 2025, prices for Chicago to San Diego flights are approximately 4% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San Diego

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San Diego according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to San Diego (CHI to SAN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Diego

Best Price Found	$121
Fastest flight time	4h 10m
Direct flights	Every day
Airports in San Diego	1 airport

The best one-way flight to San Diego from Chicago in the past 72 hours is $121. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $205.

The fastest flight from Chicago to San Diego takes 4h 10m

Direct flights go from Chicago to San Diego every day.

There is 1 airport in San Diego. From Chicago there are direct flights to San Diego (SAN).

Search flight deals

How far is Chicago to San Diego by plane?
There are 1730.3 mi between Chicago and San Diego. In terms of flight time, this usually takes a little over 4h 10m.
When did momondo last update prices for flights from Chicago to San Diego Airport?
Prices for flights from Chicago to San Diego Airport refresh daily.
How many operators does momondo search for flights from Chicago to San Diego Airport?
As of December 2025, there are 8 operators available to choose from for flights from Chicago to San Diego Airport.
How old do you have to be to fly from Chicago to San Diego Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to San Diego Airport.
What documentation or ID do you need to fly to San Diego Airport?
The travel and health documents you'll need for your trip to San Diego Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Diego Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to San Diego?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San Diego is Boeing 737-800 (25.36% of total bookings). The next most popular plane models are Airbus A321neo (20.11%), Boeing 737 MAX 9 (13.44%), and Boeing 737-800 Passenger/BBJ2 (winglets) (12.49%).
What is the most popular airline from Chicago to San Diego?
Based on momondo bookings for flights between Chicago and San Diego, the leading airline is American Airlines, making up 26% of the total bookings. Other popular airlines include United Airlines with 23%, Frontier with 23%, and Alaska Airlines with 14%.

Best airlines flying from Chicago to San Diego

Compare and see reviews for airlines that fly from Chicago to San Diego with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $84	Free Cancellation	Rating 6.3 8,189 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $103	Free Cancellation	Rating 5.8 3,081 reviews	Search Frontier flights
Alaska Airlines	PriceFrom $141	Free Cancellation	Rating 8.0 11,478 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $161	Free Cancellation	Rating 7.2 11,055 reviews	Search American Airlines flights
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Hawaiian Airlines	PriceFrom $168	Free Cancellation	Rating 7.8 2,820 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $177	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights

Alaska Airlines Flights From Chicago to San Diego
Alaska Airlines flies from Chicago to San Diego around 3 times per week, with 11,478 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Chicago to San Diego in the last 72 hours was $141 (round-trip), much lower than the average airfare cost of $238 for Alaska Airlines flights on this route.
Southwest Flights From Chicago to San Diego
$177 is the best Southwest flight deal from Chicago to San Diego found on momondo over the last 72 hours. The average Southwest ticket price found was closer to $392, however, with flight time and availability significantly affecting the price. Southwest (7.9/10 from 4,250 user reviews) flies into San Diego from Chicago 12 times in an average week so prices can vary.

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Julian

National City

Poway

Imperial Beach

Borrego Springs

La Mesa

San Ysidro

Alpine

Lemon Grove

Santee

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Diego?

Finding the right flight to San Diego from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San Diego quick and easy, saving you time and money.

Can I find flights from Chicago to San Diego with flexible booking policies on momondo?

Flights from Chicago to San Diego with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to San Diego?

momondo provides multiple filters to help you find the best flight to San Diego from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San Diego right now. Can momondo alert me if prices change?

If you are simply researching potential flights to San Diego, momondo offers a useful price alert feature which will track prices for flights to San Diego from Chicago and alert you when they change.

An easier way to manage your San Diego trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago to San Diego from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Diego departing on 1/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Filter for what you want

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Our best American Airlines deals on Chicago to San Diego flight tickets

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Our best Southwest deals on Chicago to San Diego flight tickets

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Use the filters below to find and compare flights from Chicago to San Diego that are best for you.

See travel insights to San Diego from

How to get the cheapest flight ticket from Chicago to San Diego

What is the typical price of a round-trip flight between Chicago and San Diego?

What is the cheapest month to fly to San Diego?

If you are unable to visit San Diego during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $244.

What is the cheapest day to depart on your flight to San Diego?

What is the cheapest time of day to depart on your flight to San Diego?

The cheapest time of day to fly to San Diego is at noon when flights can be purchased for as low as $266. Flights in the afternoon are often more expensive with an average ticket price of $374.

What is the cheapest Chicago to San Diego flight route?

Fly from Chicago O'Hare Intl to San Diego for the best Chicago - San Diego flight prices

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

What cabin class options are available on Chicago to San Diego flights?

There are 4 cabin classes available to choose from on Chicago to San Diego flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San Diego flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago to San Diego flight.

How have Chicago to San Diego flight prices changed over time?

As of December 2025, prices for Chicago to San Diego flights are approximately 4% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to San Diego?

Southwest, United Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to San Diego

What airlines fly to San Diego?

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

The number of flights available between Chicago and San Diego is 21 per day as of December 2025. The most frequent departure time is 6:00PM, with 50% of daily flights leaving in the evening.

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

151 flights are operational weekly from Chicago to San Diego as of December 2025. The most popular departure day for this route is Thu, with 26% of flights per week taking off on this day.

When to book flights from Chicago to San Diego

Cheap Chicago to San Diego (CHI to SAN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Diego

Best Price Found

Fastest flight time

Direct flights

Airports in San Diego

How far is Chicago to San Diego by plane?

When did momondo last update prices for flights from Chicago to San Diego Airport?

How many operators does momondo search for flights from Chicago to San Diego Airport?

How old do you have to be to fly from Chicago to San Diego Airport?

What documentation or ID do you need to fly to San Diego Airport?

What is the most popular plane model from Chicago to San Diego?

What is the most popular airline from Chicago to San Diego?

Best airlines flying from Chicago to San Diego

Compare and see reviews for airlines that fly from Chicago to San Diego with momondo

Alaska Airlines Flights From Chicago to San Diego

Southwest Flights From Chicago to San Diego

Traveling to a place near San Diego?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Diego?

Can I find flights from Chicago to San Diego with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to San Diego?

I’m not ready to book a flight from Chicago to San Diego right now. Can momondo alert me if prices change?

An easier way to manage your San Diego trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing California