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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 1/20. 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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0 bags

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Cheap round-trip flights

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Frontier Logo
6:30 pm - 12:09 am
ORD
-
SAN
7h 39m1 stop
Frontier Logo
9:00 am - 1:07 am
SAN
-
ORD
14h 07m1 stop
$159Frontier
Fri, Mar 13 - Mon, Mar 16
Southwest Logo
8:05 am - 10:40 am
MDW
-
SAN
4h 35mnonstop
Southwest Logo
6:30 pm - 12:25 am
SAN
-
MDW
3h 55mnonstop
$160Southwest
Sat, Feb 14 - Tue, Feb 17
Multiple Airlines Logo
9:00 am - 5:03 pm
ORD
-
SAN
10h 03m1 stop
Multiple Airlines Logo
5:10 pm - 11:37 pm
SAN
-
ORD
4h 27mnonstop
$160Multiple Airlines
Thu, Jan 22 - Thu, Jan 29
Frontier Logo
4:31 pm - 7:31 pm
ORD
-
SAN
29h 00m1 stop
Frontier Logo
6:30 am - 6:31 pm
SAN
-
ORD
10h 01m1 stop
$161Frontier
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
5:49 pm - 8:23 pm
ORD
-
SAN
4h 34mnonstop
American Airlines Logo
6:15 am - 12:22 pm
SAN
-
ORD
4h 07mnonstop
$162American Airlines
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
2:40 pm - 8:49 pm
ORD
-
SAN
8h 09m1 stop
United Airlines Logo
2:11 pm - 8:25 pm
SAN
-
ORD
4h 14mnonstop
$163United Airlines
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
7:40 pm - 10:10 pm
MDW
-
SAN
4h 30mnonstop
Southwest Logo
7:25 am - 4:45 pm
SAN
-
MDW
7h 20m2 stops
$163Southwest
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
12:00 pm - 12:40 pm
ORD
-
SAN
26h 40m1 stop
Frontier Logo
11:50 am - 9:24 pm
SAN
-
ORD
7h 34m1 stop
$164Frontier
Tue, Jan 13 - Sun, Jan 18
Alaska Airlines Logo
3:44 pm - 6:26 pm
ORD
-
SAN
4h 42mnonstop
Alaska Airlines Logo
5:10 pm - 11:37 pm
SAN
-
ORD
4h 27mnonstop
$166Alaska Airlines
Fri, Jan 23 - Sat, Jan 31
Alaska Airlines Logo
3:07 pm - 5:52 pm
ORD
-
SAN
4h 45mnonstop
Alaska Airlines Logo
8:35 am - 2:58 pm
SAN
-
ORD
4h 23mnonstop
$167Alaska Airlines
Fri, Feb 27 - Sat, Mar 7

Alaska Airlines flights from Chicago to San Diego

Our best Alaska Airlines deals on Chicago to San Diego flight tickets
Alaska Airlines
Jan 23
ORD3:44 pmChicago O'Hare Intl
4h 42m
SAN6:26 pmSan Diego
Jan 31
SAN8:00 amSan Diego
4h 29m
ORD2:29 pmChicago O'Hare Intl
$166
Find similar
Alaska Airlines
Feb 14
ORD3:07 pmChicago O'Hare Intl
4h 45m
SAN5:52 pmSan Diego
Mar 23
SAN5:38 pmSan Diego
4h 21m
ORD11:59 pmChicago O'Hare Intl
$167
Find similar
Alaska Airlines
Jan 17
ORD3:44 pmChicago O'Hare Intl
4h 42m
SAN6:26 pmSan Diego
Jan 18
SAN5:10 pmSan Diego
4h 27m
ORD11:37 pmChicago O'Hare Intl
$187
Find similar

United Airlines flights from Chicago to San Diego

Our best United Airlines deals on Chicago to San Diego flight tickets
United Airlines
Jan 17
ORD2:40 pmChicago O'Hare Intl
8h 09m
1 stop
SAN8:49 pmSan Diego
Jan 24
SAN2:11 pmSan Diego
4h 14m
ORD8:25 pmChicago O'Hare Intl
$163
Find similar
United Airlines
Jan 28
ORD2:40 pmChicago O'Hare Intl
8h 09m
1 stop
SAN8:49 pmSan Diego
Jan 30
SAN2:11 pmSan Diego
4h 14m
ORD8:25 pmChicago O'Hare Intl
$173
Find similar
United Airlines
Jan 23
ORD1:00 pmChicago O'Hare Intl
4h 33m
SAN3:33 pmSan Diego
Jan 30
SAN2:11 pmSan Diego
4h 14m
ORD8:25 pmChicago O'Hare Intl
$177
Find similar

momondo Fare Finder

 
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, momondo users made 832,500 searches. Data last updated December 28, 2025.
Use the filters below to find and compare flights from Chicago to San Diego that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 3/13

6:30 pm-12:09 am

1 stop7h 39m

San Diego

Mon 3/16

9:00 am-1:07 am

1 stop14h 07m

$159

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 2/14

8:05 am-10:40 am

Nonstop4h 35m

San Diego

Tue 2/17

6:30 pm-12:25 am

Nonstop3h 55m

$160

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 1/22

9:00 am-5:03 pm

1 stop10h 03m

San Diego

Thu 1/29

5:10 pm-11:37 pm

Nonstop4h 27m

$160

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 1/15

4:31 pm-7:31 pm

1 stop29h 00m

San Diego

Thu 1/22

6:30 am-6:31 pm

1 stop10h 01m

$161

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 2/14

5:49 pm-8:23 pm

Nonstop4h 34m

San Diego

Tue 2/17

6:15 am-12:22 pm

Nonstop4h 07m

$162

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 1/17

2:40 pm-8:49 pm

1 stop8h 09m

San Diego

Sat 1/24

2:11 pm-8:25 pm

Nonstop4h 14m

$163

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 1/17

7:40 pm-10:10 pm

Nonstop4h 30m

San Diego

Sat 1/24

7:25 am-4:45 pm

2 stops7h 20m

$163

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Tue 1/13

12:00 pm-12:40 pm

1 stop26h 40m

San Diego

Sun 1/18

11:50 am-9:24 pm

1 stop7h 34m

$164

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 1/23

3:44 pm-6:26 pm

Nonstop4h 42m

San Diego

Sat 1/31

5:10 pm-11:37 pm

Nonstop4h 27m

$166

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 2/27

3:07 pm-5:52 pm

Nonstop4h 45m

San Diego

Sat 3/7

8:35 am-2:58 pm

Nonstop4h 23m

$167

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 $295. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $376. 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 $370.

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 $308 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 $250 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

$125

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 $125. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $194.
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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $84Free CancellationRating
6.3
8,211 reviews
Search Spirit Airlines flights
FrontierPriceFrom $103Free CancellationRating
5.8
3,070 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $142Free CancellationRating
8.0
11,548 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $153Free CancellationRating
7.8
2,819 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $161Free CancellationRating
7.2
11,069 reviews
Search American Airlines flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
SouthwestPriceFrom $172Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,021 reviews
Search Delta flights

  • Alaska Airlines Flights From Chicago to San Diego

    Alaska Airlines flies from Chicago to San Diego around 15 times per week, with 11,547 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Chicago to San Diego in the last 72 hours was $142 (round-trip), much lower than the average airfare cost of $247 for Alaska Airlines flights on this route.

  • Southwest Flights From Chicago to San Diego

    $172 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 $389, however, with flight time and availability significantly affecting the price. Southwest (8.0/10 from 4,256 user reviews) flies into San Diego from Chicago 20 times in an average week so prices can vary.

Traveling to a place near San Diego?

Book flights to San Diego if you plan to visit one of these locations
Coronado
Chula Vista
El Cajon
Julian
Poway
National City
Borrego Springs
Imperial Beach
La Mesa
San Ysidro
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.
Start using Trips
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