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Cheap flights from Chicago to San Diego from $77

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 12/17. 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

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United Airlines Logo
2:40 pm - 8:49 pmORD-SAN
8h 09m1 stop
United Airlines Logo
7:00 am - 1:13 pmSAN-ORD
4h 13mnonstop
$161United Airlines
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Tue, Jan 13 - Tue, Jan 20
Frontier Logo
9:09 pm - 11:31 pmMDW-SAN
28h 22m1 stop
Frontier Logo
6:30 am - 10:19 pmSAN-MDW
13h 49m2 stops
$162Frontier
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Mon, Jan 19 - Fri, Jan 23
Frontier Logo
9:38 pm - 8:51 amORD-SAN
13h 13m1 stop
Frontier Logo
6:30 am - 10:46 pmSAN-ORD
14h 16m2 stops
$162Frontier
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Sun, Jan 25 - Fri, Jan 30
Southwest Logo
1:55 pm - 4:15 pmMDW-SAN
4h 20mnonstop
Southwest Logo
3:15 pm - 10:55 pmSAN-MDW
5h 40m1 stop
$163Southwest
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Wed, Dec 24 - Wed, Dec 31
Multiple Airlines Logo
9:38 pm - 8:51 amORD-SAN
13h 13m1 stop
Multiple Airlines Logo
5:10 pm - 11:37 pmSAN-ORD
4h 27mnonstop
$163Multiple Airlines
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Sun, Jan 25 - Fri, Jan 30
Frontier Logo
9:53 pm - 2:10 pmORD-SAN
18h 17m1 stop
Frontier Logo
6:34 am - 12:12 amSAN-ORD
15h 38m1 stop
$164Frontier
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Thu, Dec 11 - Mon, Dec 15
Southwest Logo
7:40 pm - 10:10 pmMDW-SAN
4h 30mnonstop
Southwest Logo
7:30 pm - 5:05 amSAN-MDW
7h 35m1 stop
$165Southwest
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Sat, Jan 10 - Sat, Jan 17
Alaska Airlines Logo
8:55 am - 11:22 amORD-SAN
4h 27mnonstop
Alaska Airlines Logo
1:45 pm - 7:54 pmSAN-ORD
4h 09mnonstop
$165Alaska Airlines
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Thu, Dec 11 - Wed, Dec 17
Alaska Airlines Logo
3:05 pm - 5:33 pmORD-SAN
4h 28mnonstop
Alaska Airlines Logo
8:00 am - 2:09 pmSAN-ORD
4h 09mnonstop
$167Alaska Airlines
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Mon, Dec 8 - Sat, Dec 13
American Airlines Logo
8:15 am - 10:48 amORD-SAN
4h 33mnonstop
American Airlines Logo
6:20 am - 12:29 pmSAN-ORD
4h 09mnonstop
$170American Airlines
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Wed, Dec 17 - Sun, Jan 11

Alaska Airlines flights from Chicago to San Diego

Our best Alaska Airlines deals on Chicago to San Diego flight tickets
Alaska Airlines
Dec 11
ORD8:55 amChicago O'Hare Intl
4h 27m
SAN11:22 amSan Diego
Dec 17
SAN1:45 pmSan Diego
4h 09m
ORD7:54 pmChicago O'Hare Intl
$165
Find similar
Alaska Airlines
Dec 8
ORD3:05 pmChicago O'Hare Intl
4h 28m
SAN5:33 pmSan Diego
Dec 13
SAN8:00 amSan Diego
4h 09m
ORD2:09 pmChicago O'Hare Intl
$167
Find similar
Alaska Airlines
Dec 17
ORD3:05 pmChicago O'Hare Intl
4h 28m
SAN5:33 pmSan Diego
Dec 24
SAN1:30 pmSan Diego
4h 32m
ORD8:02 pmChicago O'Hare Intl
$175
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American Airlines flights from Chicago to San Diego

Our best American Airlines deals on Chicago to San Diego flight tickets
American Airlines
Dec 17
ORD8:15 amChicago O'Hare Intl
4h 33m
SAN10:48 amSan Diego
Jan 11
SAN6:20 amSan Diego
4h 09m
ORD12:29 pmChicago O'Hare Intl
$170
Find similar
American Airlines
Feb 25
ORD5:49 pmChicago O'Hare Intl
4h 36m
SAN8:25 pmSan Diego
Mar 1
SAN3:23 pmSan Diego
4h 07m
ORD9:30 pmChicago O'Hare Intl
$178
Find similar
American Airlines
Dec 16
ORD6:10 pmChicago O'Hare Intl
4h 35m
SAN8:45 pmSan Diego
Dec 23
SAN3:03 pmSan Diego
4h 27m
ORD9:30 pmChicago O'Hare Intl
$188
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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 November 18, 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

Tue 1/13

2:40 pm-8:49 pm

1 stop8h 09m

San Diego

Tue 1/20

7:00 am-1:13 pm

Nonstop4h 13m

$161

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 1/19

9:09 pm-11:31 pm

1 stop28h 22m

San Diego

Fri 1/23

6:30 am-10:19 pm

2 stops13h 49m

$162

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 1/25

9:38 pm-8:51 am

1 stop13h 13m

San Diego

Fri 1/30

6:30 am-10:46 pm

2 stops14h 16m

$162

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 12/24

1:55 pm-4:15 pm

Nonstop4h 20m

San Diego

Wed 12/31

3:15 pm-10:55 pm

1 stop5h 40m

$163

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sun 1/25

9:38 pm-8:51 am

1 stop13h 13m

San Diego

Fri 1/30

5:10 pm-11:37 pm

Nonstop4h 27m

$163

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 12/11

9:53 pm-2:10 pm

1 stop18h 17m

San Diego

Mon 12/15

6:34 am-12:12 am

1 stop15h 38m

$164

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 1/10

7:40 pm-10:10 pm

Nonstop4h 30m

San Diego

Sat 1/17

7:30 pm-5:05 am

1 stop7h 35m

$165

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 12/11

8:55 am-11:22 am

Nonstop4h 27m

San Diego

Wed 12/17

1:45 pm-7:54 pm

Nonstop4h 09m

$165

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 12/8

3:05 pm-5:33 pm

Nonstop4h 28m

San Diego

Sat 12/13

8:00 am-2:09 pm

Nonstop4h 09m

$167

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Wed 12/17

8:15 am-10:48 am

Nonstop4h 33m

San Diego

Sun 1/11

6:20 am-12:29 pm

Nonstop4h 09m

$170

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 $314. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $437. 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 $276. Flights in the afternoon are often more expensive with an average ticket price of $421.

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 $328 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 $255 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.

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

As of November 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

$97

Fastest flight time

4h 15m

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 $97. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $190.
The fastest flight from Chicago to San Diego takes 4h 15m
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 20m.

  • 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 $87Free CancellationRating
6.3
8,146 reviews
Search Spirit Airlines flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,103 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $142Free CancellationRating
8.0
11,316 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $165Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
Hawaiian AirlinesPriceFrom $168Free CancellationRating
7.8
2,809 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $172Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
SouthwestPriceFrom $195Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
DeltaPriceFrom $223Free CancellationRating
7.9
8,007 reviews
Search Delta flights

  • Alaska Airlines Flights From Chicago to San Diego

    Alaska Airlines flies from Chicago to San Diego around 16 times per week, with 11,316 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 $230 for Alaska Airlines flights on this route.

  • Southwest Flights From Chicago to San Diego

    $195 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 $457, however, with flight time and availability significantly affecting the price. Southwest (8.0/10 from 4,245 user reviews) flies into San Diego from Chicago 29 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
National City
Imperial Beach
La Mesa
Poway
Borrego Springs
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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