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Cheap flights from Chicago to San Diego from $74

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 9/7. 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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Cheap round-trip flights

Frontier Logo
7:30 am - 1:36 pmORD-SAN
8h 06m1 stop
Frontier Logo
4:03 pm - 10:25 pmSAN-ORD
4h 22mnonstop
$132Frontier
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Fri, Sep 26 - Sun, Sep 28
Frontier Logo
7:55 am - 10:30 amORD-SAN
4h 35mnonstop
Frontier Logo
9:03 pm - 11:59 pmSAN-ORD
24h 56m1 stop
$133Frontier
Find Deal
Sun, Sep 14 - Thu, Sep 18
Southwest Logo
8:25 pm - 10:45 pmMDW-SAN
4h 20mnonstop
Southwest Logo
4:50 pm - 10:50 pmSAN-MDW
4h 00mnonstop
$139Southwest
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Wed, Oct 22 - Sat, Oct 25
Alaska Airlines Logo
3:50 pm - 6:50 pmORD-SAN
5h 00mnonstop
Alaska Airlines Logo
8:00 am - 1:54 pmSAN-ORD
3h 54mnonstop
$139Alaska Airlines
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Tue, Oct 14 - Tue, Oct 28
United Airlines Logo
4:00 pm - 6:20 pmORD-SAN
4h 20mnonstop
United Airlines Logo
2:11 pm - 8:25 pmSAN-ORD
4h 14mnonstop
$149United Airlines
Find Deal
Sat, Sep 20 - Sat, Sep 27
Southwest Logo
7:25 pm - 9:35 pmMDW-SAN
4h 10mnonstop
Southwest Logo
10:45 am - 4:45 pmSAN-MDW
4h 00mnonstop
$149Southwest
Find Deal
Sat, Sep 20 - Sat, Sep 27
Alaska Airlines Logo
7:59 pm - 10:59 pmORD-SAN
5h 00mnonstop
Alaska Airlines Logo
1:52 pm - 12:24 amSAN-ORD
8h 32m1 stop
$175Alaska Airlines
Find Deal
Wed, Oct 15 - Tue, Oct 28
United Airlines Logo
7:35 pm - 10:02 pmORD-SAN
4h 27mnonstop
United Airlines Logo
5:01 pm - 11:14 pmSAN-ORD
4h 13mnonstop
$178United Airlines
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Tue, Sep 23 - Fri, Sep 26
Spirit Airlines Logo
12:46 pm - 6:42 pmORD-SAN
7h 56m1 stop
Spirit Airlines Logo
6:15 am - 4:59 pmSAN-ORD
8h 44m1 stop
$180Spirit Airlines
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Sat, Sep 6 - Mon, Sep 8
Spirit Airlines Logo
5:35 pm - 11:37 pmORD-SAN
8h 02m1 stop
Spirit Airlines Logo
6:15 am - 6:14 pmSAN-ORD
9h 59m2 stops
$183Spirit Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 17

Frontier flights from Chicago to San Diego

Our best Frontier deals on Chicago to San Diego flight tickets
Frontier
Sep 26
ORD7:30 amChicago O'Hare Intl
8h 06m
1 stop
SAN1:36 pmSan Diego
Sep 28
SAN4:03 pmSan Diego
4h 22m
ORD10:25 pmChicago O'Hare Intl
$132
Find similar
Frontier
Sep 14
ORD7:55 amChicago O'Hare Intl
4h 35m
SAN10:30 amSan Diego
Sep 18
SAN9:03 pmSan Diego
24h 56m
1 stop
ORD11:59 pmChicago O'Hare Intl
$133
Find similar
Frontier
Oct 23
ORD7:15 amChicago O'Hare Intl
4h 22m
SAN9:37 amSan Diego
Oct 27
SAN4:06 pmSan Diego
4h 18m
ORD10:24 pmChicago O'Hare Intl
$136
Find similar

Delta flights from Chicago to San Diego

Our best Delta deals on Chicago to San Diego flight tickets
Delta
Sep 9
MDW1:08 pmChicago Midway
6h 56m
1 stop
SAN6:04 pmSan Diego
Sep 12
SAN10:15 pmSan Diego
8h 25m
1 stop
MDW8:40 amChicago Midway
$278
Find similar
Delta
Aug 31
MDW9:31 amChicago Midway
6h 27m
1 stop
SAN1:58 pmSan Diego
Sep 16
SAN10:15 pmSan Diego
8h 25m
1 stop
MDW8:40 amChicago Midway
$287
Find similar
Delta
Sep 9
MDW1:08 pmChicago Midway
6h 56m
1 stop
SAN6:04 pmSan Diego
Sep 14
SAN6:15 amSan Diego
9h 20m
1 stop
MDW5:35 pmChicago Midway
$307
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 August 26, 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 9/26

7:30 am-1:36 pm

1 stop8h 06m

San Diego

Sun 9/28

4:03 pm-10:25 pm

Nonstop4h 22m

$132

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 9/14

7:55 am-10:30 am

Nonstop4h 35m

San Diego

Thu 9/18

9:03 pm-11:59 pm

1 stop24h 56m

$133

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 10/22

8:25 pm-10:45 pm

Nonstop4h 20m

San Diego

Sat 10/25

4:50 pm-10:50 pm

Nonstop4h 00m

$139

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Tue 10/14

3:50 pm-6:50 pm

Nonstop5h 00m

San Diego

Tue 10/28

8:00 am-1:54 pm

Nonstop3h 54m

$139

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 9/20

4:00 pm-6:20 pm

Nonstop4h 20m

San Diego

Sat 9/27

2:11 pm-8:25 pm

Nonstop4h 14m

$149

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 9/20

7:25 pm-9:35 pm

Nonstop4h 10m

San Diego

Sat 9/27

10:45 am-4:45 pm

Nonstop4h 00m

$149

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 10/15

7:59 pm-10:59 pm

Nonstop5h 00m

San Diego

Tue 10/28

1:52 pm-12:24 am

1 stop8h 32m

$175

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Tue 9/23

7:35 pm-10:02 pm

Nonstop4h 27m

San Diego

Fri 9/26

5:01 pm-11:14 pm

Nonstop4h 13m

$178

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 9/6

12:46 pm-6:42 pm

1 stop7h 56m

San Diego

Mon 9/8

6:15 am-4:59 pm

1 stop8h 44m

$180

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 8/30

5:35 pm-11:37 pm

1 stop8h 02m

San Diego

Wed 9/17

6:15 am-6:14 pm

2 stops9h 59m

$183

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 August, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $277.

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 $382. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $466. 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 $285. Flights in the afternoon are often more expensive with an average ticket price of $450.

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 $376 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 $289 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 16% 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 August 2025, prices for Chicago to San Diego flights are approximately 11% 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

$88

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 $88. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $168.
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)
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 $93Free CancellationRating
6.3
8,031 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.8
3,200 reviews
Search Frontier flights
Hawaiian AirlinesPriceFrom $138Free CancellationRating
7.8
2,681 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $139Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $167Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $233Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $240Free CancellationRating
7.9
7,979 reviews
Search Delta flights
United AirlinesPriceFrom $244Free CancellationRating
7.4
8,943 reviews
Search United Airlines flights

  • Alaska Airlines Flights From Chicago to San Diego

    Alaska Airlines flies from Chicago to San Diego around 11 times per week, with 10,000 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Chicago to San Diego in the last 72 hours was $139 (round-trip), much lower than the average airfare cost of $425 for Alaska Airlines flights on this route.

  • Southwest Flights From Chicago to San Diego

    $233 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 $462, however, with flight time and availability significantly affecting the price. Southwest (8.0/10 from 4,243 user reviews) flies into San Diego from Chicago 18 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
La Mesa
National City
Imperial Beach
Poway
San Ysidro
Borrego Springs
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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