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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 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:40 pm - 11:10 pm
MDW
-
SAN
4h 30mnonstop
Southwest Logo
6:30 pm - 12:25 am
SAN
-
MDW
3h 55mnonstop
$157Southwest
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
8:00 pm - 10:34 pm
ORD
-
SAN
4h 34mnonstop
American Airlines Logo
10:35 pm - 4:39 am
SAN
-
ORD
4h 04mnonstop
$157American Airlines
Sat, Feb 14 - Tue, Feb 17
Frontier Logo
7:00 am - 2:31 pm
ORD
-
SAN
9h 31m
1 stop
Frontier Logo
9:18 pm - 9:43 am
SAN
-
ORD
10h 25m
1 stop
$158Frontier
Tue, Mar 10 - Sat, Mar 14
Frontier Logo
12:53 pm - 11:28 am
ORD
-
SAN
24h 35m
1 stop
Frontier Logo
9:45 am - 10:26 am
SAN
-
ORD
22h 41m
1 stop
$160Frontier
Fri, Feb 20 - Wed, Feb 25
American Airlines Logo
8:45 pm - 11:16 pm
ORD
-
SAN
4h 31mnonstop
American Airlines Logo
3:07 pm - 9:28 pm
SAN
-
ORD
4h 21mnonstop
$161American Airlines
Wed, Apr 22 - Sat, Apr 25
United Airlines Logo
7:59 pm - 10:44 pm
ORD
-
SAN
4h 45mnonstop
United Airlines Logo
7:50 pm - 5:07 am
SAN
-
ORD
7h 17m
1 stop
$163United Airlines
Wed, Mar 4 - Sat, Mar 7
Frontier Logo
10:36 pm - 2:05 pm
MDW
-
SAN
17h 29m
1 stop
Frontier Logo
6:45 am - 11:13 pm
SAN
-
MDW
14h 28m
1 stop
$163Frontier
Mon, Mar 30 - Mon, Apr 6
Alaska Airlines Logo
3:44 pm - 6:26 pm
ORD
-
SAN
4h 42mnonstop
Alaska Airlines Logo
5:42 pm - 11:59 pm
SAN
-
ORD
4h 17mnonstop
$164Alaska Airlines
Mon, Feb 9 - Fri, Feb 13
Multiple Airlines Logo
9:05 am - 8:24 pm
ORD
-
SAN
13h 19m
1 stop
Multiple Airlines Logo
5:42 pm - 11:59 pm
SAN
-
ORD
4h 17mnonstop
$168Multiple Airlines
Tue, Feb 24 - Fri, Feb 27
Multiple Airlines Logo
8:00 am - 1:57 pm
ORD
-
SAN
7h 57m
1 stop
Multiple Airlines Logo
5:10 pm - 11:37 pm
SAN
-
ORD
4h 27mnonstop
$169Multiple Airlines
Mon, Feb 9 - Tue, Feb 10

Southwest flights from Chicago to San Diego

Our best Southwest deals on Chicago to San Diego flight tickets
Southwest
Feb 14
MDW8:40 pmChicago Midway
4h 30m
SAN11:10 pmSan Diego
Feb 17
SAN6:30 pmSan Diego
3h 55m
MDW12:25 amChicago Midway
$157
Southwest
Mar 6
MDW8:55 pmChicago Midway
4h 30m
SAN11:25 pmSan Diego
Mar 10
SAN6:30 amSan Diego
4h 05m
MDW12:35 pmChicago Midway
$167
Southwest
Feb 14
MDW8:40 pmChicago Midway
4h 30m
SAN11:10 pmSan Diego
Feb 17
SAN6:30 pmSan Diego
3h 55m
MDW12:25 amChicago Midway
$169

American Airlines flights from Chicago to San Diego

Our best American Airlines deals on Chicago to San Diego flight tickets
American Airlines
Feb 14
ORD8:00 pmChicago O'Hare Intl
4h 34m
SAN10:34 pmSan Diego
Feb 17
SAN10:35 pmSan Diego
4h 04m
ORD4:39 amChicago O'Hare Intl
$157
American Airlines
Apr 22
ORD8:45 pmChicago O'Hare Intl
4h 31m
SAN11:16 pmSan Diego
Apr 25
SAN3:07 pmSan Diego
4h 21m
ORD9:28 pmChicago O'Hare Intl
$161
American Airlines
Feb 14
ORD5:49 pmChicago O'Hare Intl
4h 31m
SAN8:20 pmSan Diego
Feb 20
SAN3:19 pmSan Diego
4h 16m
ORD9:35 pmChicago O'Hare Intl
$167

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 January 20, 2026.
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

MDW - SAN

MDWSAN

Chicago Midway

Sat 2/14

8:40 pm-11:10 pm

Nonstop4h 30m

San Diego

Tue 2/17

6:30 pm-12:25 am

Nonstop3h 55m

$157

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 2/14

8:00 pm-10:34 pm

Nonstop4h 34m

San Diego

Tue 2/17

10:35 pm-4:39 am

Nonstop4h 04m

$157

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Tue 3/10

7:00 am-2:31 pm

1 stop9h 31m

San Diego

Sat 3/14

9:18 pm-9:43 am

1 stop10h 25m

$158

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Fri 2/20

12:53 pm-11:28 am

1 stop24h 35m

San Diego

Wed 2/25

9:45 am-10:26 am

1 stop22h 41m

$160

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 4/22

8:45 pm-11:16 pm

Nonstop4h 31m

San Diego

Sat 4/25

3:07 pm-9:28 pm

Nonstop4h 21m

$161

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 3/4

7:59 pm-10:44 pm

Nonstop4h 45m

San Diego

Sat 3/7

7:50 pm-5:07 am

1 stop7h 17m

$163

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 3/30

10:36 pm-2:05 pm

1 stop17h 29m

San Diego

Mon 4/6

6:45 am-11:13 pm

1 stop14h 28m

$163

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 2/9

3:44 pm-6:26 pm

Nonstop4h 42m

San Diego

Fri 2/13

5:42 pm-11:59 pm

Nonstop4h 17m

$164

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Tue 2/24

9:05 am-8:24 pm

1 stop13h 19m

San Diego

Fri 2/27

5:42 pm-11:59 pm

Nonstop4h 17m

$168

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 2/9

8:00 am-1:57 pm

1 stop7h 57m

San Diego

Tue 2/10

5:10 pm-11:37 pm

Nonstop4h 27m

$169

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 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 February is also very affordable. Most momondo users find prices during this month for around $237.

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 Saturday. Travelers who choose to depart for San Diego on a Saturday will often find tickets for as low as $284. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $364. 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 $263. Flights in the afternoon are often more expensive with an average ticket price of $350.

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 $298 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 $225 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 3% 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 January 2026, prices for Chicago to San Diego flights are approximately 8% more expensive 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

$115

Fastest flight time

4h 05m

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 $115. 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 05m
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 05m.

  • 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
8,350 reviews
Search Spirit Airlines flights
FrontierPriceFrom $98Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
DeltaPriceFrom $128Free CancellationRating
7.9
8,077 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $138Free CancellationRating
7.8
2,829 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $142Free CancellationRating
8.0
11,760 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
9,179 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,164 reviews
Search American Airlines flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,267 reviews
Search Southwest flights

  • Alaska Airlines Flights From Chicago to San Diego

    Alaska Airlines flies from Chicago to San Diego around 8 times per week, with 11,764 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 $256 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 $372, however, with flight time and availability significantly affecting the price. Southwest (8.0/10 from 4,266 user reviews) flies into San Diego from Chicago 16 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
Imperial Beach
San Ysidro
Borrego Springs
La Mesa
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.
Start using Trips
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