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

278 flights are operational weekly from Chicago to San Diego as of July 2025. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.

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

The number of flights available between Chicago and San Diego is 39 per day as of July 2025. The most frequent departure time is 4:00PM, with 44% of daily flights leaving in the afternoon.

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

Spirit Airlines, Southwest, and Frontier are the most popular carriers operating from Chicago to San Diego

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 54% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 7 different airlines that fly to San Diego on a routine basis, so you have a few additional options to choose from.

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 July 2025, there are 7 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.

$43 Cheap Flights from Chicago to San Diego in 2025

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Find the cheapest flights from Chicago to San Diego

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:10 am - 9:30 amMDW-SAN

4h 20mnonstop

6:25 pm - 12:25 amSAN-MDW

4h 00mnonstop

$104Southwest

Find Deal

Tue, Oct 7 - Wed, Oct 15

8:50 pm - 11:05 pmMDW-SAN

4h 15mnonstop

10:40 am - 4:40 pmSAN-MDW

4h 00mnonstop

$109Southwest

Find Deal

Mon, Aug 25 - Wed, Sep 3

8:50 pm - 11:05 pmMDW-SAN

4h 15mnonstop

1:40 pm - 7:40 pmSAN-MDW

4h 00mnonstop

$114Southwest

Find Deal

Thu, Aug 14 - Thu, Aug 21

1:39 pm - 3:59 pmORD-SAN

4h 20mnonstop

4:44 pm - 11:07 pmSAN-ORD

4h 23mnonstop

$115Frontier

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Wed, Aug 6 - Sat, Aug 9

7:08 am - 5:55 pmORD-SAN

12h 47m1 stop

7:00 pm - 6:03 amSAN-ORD

9h 03m1 stop

$116Spirit Airlines

Find Deal

Tue, Aug 5 - Wed, Aug 6

7:08 am - 5:55 pmORD-SAN

12h 47m1 stop

7:00 pm - 6:03 amSAN-ORD

9h 03m1 stop

$117Spirit Airlines

Find Deal

Tue, Aug 5 - Wed, Aug 6

7:00 am - 9:20 amORD-SAN

4h 20mnonstop

3:40 pm - 10:03 pmSAN-ORD

4h 23mnonstop

$121Frontier

Find Deal

Fri, Aug 29 - Mon, Sep 1

8:20 pm - 10:44 pmORD-SAN

4h 24mnonstop

10:30 pm - 4:37 amSAN-ORD

4h 07mnonstop

$143United Airlines

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Mon, Aug 18 - Tue, Aug 26

9:00 pm - 11:23 pmORD-SAN

4h 23mnonstop

2:57 pm - 9:14 pmSAN-ORD

4h 17mnonstop

$144American Airlines

Find Deal

Mon, Aug 18 - Tue, Aug 26

7:35 pm - 10:02 pmORD-SAN

4h 27mnonstop

4:11 pm - 12:45 amSAN-ORD

6h 34m1 stop

$149United Airlines

Find Deal

Thu, Aug 21 - Mon, Aug 25

Southwest flights from Chicago to San Diego

Our best Southwest deals on Chicago to San Diego flight tickets

Southwest

Oct 7

MDW7:10 amChicago Midway

4h 20m

SAN9:30 amSan Diego

Oct 15

SAN6:25 pmSan Diego

4h 00m

MDW12:25 amChicago Midway

$104

Find similar

Southwest

Aug 25

MDW8:50 pmChicago Midway

4h 15m

SAN11:05 pmSan Diego

Sep 3

SAN10:40 amSan Diego

4h 00m

MDW4:40 pmChicago Midway

$109

Find similar

Southwest

Aug 14

MDW8:50 pmChicago Midway

4h 15m

SAN11:05 pmSan Diego

Aug 21

SAN1:40 pmSan Diego

4h 00m

MDW7:40 pmChicago Midway

$114

Find similar

Frontier flights from Chicago to San Diego

Our best Frontier deals on Chicago to San Diego flight tickets

Frontier

Aug 6

ORD1:39 pmChicago O'Hare Intl

4h 20m

SAN3:59 pmSan Diego

Aug 9

SAN4:44 pmSan Diego

4h 23m

ORD11:07 pmChicago O'Hare Intl

$115

Find similar

Frontier

Aug 29

ORD7:00 amChicago O'Hare Intl

4h 20m

SAN9:20 amSan Diego

Sep 1

SAN3:40 pmSan Diego

4h 23m

ORD10:03 pmChicago O'Hare Intl

$121

Find similar

Frontier

Aug 28

ORD7:00 amChicago O'Hare Intl

4h 20m

SAN9:20 amSan Diego

Sep 1

SAN3:40 pmSan Diego

4h 23m

ORD10:03 pmChicago O'Hare Intl

$122

Find similar

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 cheapest month to fly to San Diego?

If you are unable to visit San Diego during the month of June, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $308.

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 Wednesday. Travelers who choose to depart for San Diego on a Wednesday will often find tickets for as low as $395. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $471. 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 $319. Flights in the evening are often more expensive with an average ticket price of $462.

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 $397 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 $311 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?

No. A direct flight is the cheapest option for a flight between Chicago to San Diego.

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

As of July 2025, prices for Chicago to San Diego flights are approximately 28% 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	$43
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 $43. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $104.

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 near San Diego: San Diego (SAN)

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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 July 2025, there are 7 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 (32.47% of total bookings). The next most popular plane models are Airbus A321-100/200 (13.35%), Airbus A321neo (13.20%), and Boeing 737-900 (9.90%).
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 30% of the total bookings. Other popular airlines include United Airlines with 29%, Frontier with 23%, and Southwest with 13%.

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 $93	Free Cancellation	Rating 6.3 8,055 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $108	Free Cancellation	Rating 5.9 3,271 reviews	Search Frontier flights
American Airlines	PriceFrom $200	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $218	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $237	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Delta	PriceFrom $240	Free Cancellation	Rating 8.0 7,952 reviews	Search Delta flights
United Airlines	PriceFrom $255	Free Cancellation	Rating 7.4 8,846 reviews	Search United Airlines flights

Southwest Flights From Chicago to San Diego
Southwest flies from Chicago to San Diego around 18 times per week, with 4,250 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to San Diego in the last 72 hours was $218 (round-trip), much lower than the average airfare cost of $466 for Southwest flights on this route.
Alaska Airlines Flights From Chicago to San Diego
$237 is the best Alaska Airlines flight deal from Chicago to San Diego found on momondo over the last 72 hours. The average Alaska Airlines ticket price found was closer to $496, however, with flight time and availability significantly affecting the price. Alaska Airlines (8.0/10 from 10,000 user reviews) flies into San Diego from Chicago 34 times in an average week so prices can vary.

Coronado

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Chula Vista

Julian

National City

La Mesa

Imperial Beach

San Ysidro

Poway

Borrego Springs

Lemon Grove

Alpine

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 $43

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 7/29. 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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Cheap round-trip flights

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Southwest flights from Chicago to San Diego

Our best Southwest deals on Chicago to San Diego flight tickets

Frontier flights from Chicago to San Diego

Our best Frontier deals on Chicago to San Diego flight tickets

See travel insights to San Diego from

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

What is the cheapest month to fly to San Diego?

If you are unable to visit San Diego during the month of June, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $308.

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 $319. Flights in the evening are often more expensive with an average ticket price of $462.

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?

No. A direct flight is the cheapest option for a flight between Chicago to San Diego.

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

As of July 2025, prices for Chicago to San Diego flights are approximately 28% cheaper when compared to flights at the same time last year.

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

Spirit Airlines, Southwest, and Frontier 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 39 per day as of July 2025. The most frequent departure time is 4:00PM, with 44% of daily flights leaving in the afternoon.

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

278 flights are operational weekly from Chicago to San Diego as of July 2025. The most popular departure day for this route is Thu, with 17% 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

Southwest Flights From Chicago to San Diego

Alaska Airlines 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