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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 1/27. 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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Alaska Airlines Logo
3:49 pm - 6:31 pmORD-SAN
4h 42mnonstop
Alaska Airlines Logo
5:10 pm - 11:37 pmSAN-ORD
4h 27mnonstop
$157Alaska Airlines
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Wed, Jan 7 - Tue, Jan 13
Frontier Logo
9:07 pm - 12:23 pmMDW-SAN
17h 16m1 stop
Frontier Logo
1:43 pm - 1:07 pmSAN-MDW
21h 24m2 stops
$158Frontier
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Fri, Jan 9 - Wed, Jan 14
Multiple Airlines Logo
6:38 pm - 12:23 pmORD-SAN
19h 45m2 stops
Multiple Airlines Logo
6:25 am - 6:50 pmSAN-ORD
10h 25m1 stop
$158Multiple Airlines
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Mon, Jan 5 - Thu, Jan 15
Multiple Airlines Logo
7:30 am - 3:14 pmORD-SAN
9h 44m1 stop
Multiple Airlines Logo
5:49 pm - 11:59 pmSAN-ORD
4h 10mnonstop
$159Multiple Airlines
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Mon, Nov 17 - Thu, Nov 20
Southwest Logo
8:35 pm - 11:05 pmMDW-SAN
4h 30mnonstop
Southwest Logo
7:15 am - 1:15 pmSAN-MDW
4h 00mnonstop
$160Southwest
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Thu, Feb 19 - Sat, Feb 21
United Airlines Logo
7:10 am - 9:52 amORD-SAN
4h 42mnonstop
United Airlines Logo
7:50 pm - 5:03 amSAN-ORD
7h 13m1 stop
$163United Airlines
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Sat, Feb 21 - Wed, Feb 25
United Airlines Logo
2:21 pm - 8:05 pmORD-SAN
7h 44m1 stop
United Airlines Logo
10:30 pm - 4:34 amSAN-ORD
4h 04mnonstop
$164United Airlines
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Mon, Nov 24 - Wed, Nov 26
Southwest Logo
6:05 am - 8:30 amMDW-SAN
4h 25mnonstop
Southwest Logo
6:35 am - 12:40 pmSAN-MDW
4h 05mnonstop
$165Southwest
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Tue, Nov 25 - Fri, Nov 28
American Airlines Logo
7:50 pm - 10:26 pmORD-SAN
4h 36mnonstop
American Airlines Logo
6:20 am - 12:29 pmSAN-ORD
4h 09mnonstop
$170American Airlines
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Thu, Jan 15 - Sun, Jan 18
Delta Logo
1:50 pm - 8:42 pmMDW-SAN
8h 52m1 stop
Delta Logo
10:30 pm - 9:54 amSAN-MDW
9h 24m1 stop
$237Delta
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Thu, Dec 11 - Wed, Dec 17

Southwest flights from Chicago to San Diego

Our best Southwest deals on Chicago to San Diego flight tickets
Southwest
Feb 19
MDW8:35 pmChicago Midway
4h 30m
SAN11:05 pmSan Diego
Feb 21
SAN7:15 amSan Diego
4h 00m
MDW1:15 pmChicago Midway
$160
Find similar
Southwest
Nov 25
MDW6:05 amChicago Midway
4h 25m
SAN8:30 amSan Diego
Nov 28
SAN6:35 amSan Diego
4h 05m
MDW12:40 pmChicago Midway
$165
Find similar
Southwest
Feb 21
MDW4:40 pmChicago Midway
4h 30m
SAN7:10 pmSan Diego
Feb 25
SAN7:20 amSan Diego
7h 10m
1 stop
MDW4:30 pmChicago Midway
$167
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Hawaiian Airlines flights from Chicago to San Diego

Our best Hawaiian Airlines deals on Chicago to San Diego flight tickets
Hawaiian Airlines
Nov 27
ORD8:20 amChicago O'Hare Intl
4h 26m
SAN10:46 amSan Diego
Dec 2
SAN1:45 pmSan Diego
4h 09m
ORD7:54 pmChicago O'Hare Intl
$161
Find similar
Hawaiian Airlines
Nov 8
ORD2:54 pmChicago O'Hare Intl
4h 25m
SAN5:19 pmSan Diego
Nov 11
SAN5:49 pmSan Diego
4h 10m
ORD11:59 pmChicago O'Hare Intl
$253
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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 October 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

Wed 1/7

3:49 pm-6:31 pm

Nonstop4h 42m

San Diego

Tue 1/13

5:10 pm-11:37 pm

Nonstop4h 27m

$157

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 1/9

9:07 pm-12:23 pm

1 stop17h 16m

San Diego

Wed 1/14

1:43 pm-1:07 pm

2 stops21h 24m

$158

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 1/5

6:38 pm-12:23 pm

2 stops19h 45m

San Diego

Thu 1/15

6:25 am-6:50 pm

1 stop10h 25m

$158

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 11/17

7:30 am-3:14 pm

1 stop9h 44m

San Diego

Thu 11/20

5:49 pm-11:59 pm

Nonstop4h 10m

$159

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 2/19

8:35 pm-11:05 pm

Nonstop4h 30m

San Diego

Sat 2/21

7:15 am-1:15 pm

Nonstop4h 00m

$160

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Sat 2/21

7:10 am-9:52 am

Nonstop4h 42m

San Diego

Wed 2/25

7:50 pm-5:03 am

1 stop7h 13m

$163

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Mon 11/24

2:21 pm-8:05 pm

1 stop7h 44m

San Diego

Wed 11/26

10:30 pm-4:34 am

Nonstop4h 04m

$164

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 11/25

6:05 am-8:30 am

Nonstop4h 25m

San Diego

Fri 11/28

6:35 am-12:40 pm

Nonstop4h 05m

$165

ChicagoSan Diego

ORD - SAN

ORDSAN

Chicago O'Hare Intl

Thu 1/15

7:50 pm-10:26 pm

Nonstop4h 36m

San Diego

Sun 1/18

6:20 am-12:29 pm

Nonstop4h 09m

$170

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 12/11

1:50 pm-8:42 pm

1 stop8h 52m

San Diego

Wed 12/17

10:30 pm-9:54 am

1 stop9h 24m

$237

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 $319. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $440. 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 $278. Flights in the afternoon are often more expensive with an average ticket price of $427.

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 $342 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 $269 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 October 2025, prices for Chicago to San Diego flights are approximately 13% 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

$99

Fastest flight time

4h 20m

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 $99. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $193.
The fastest flight from Chicago to San Diego takes 4h 20m
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
8,112 reviews
Search Spirit Airlines flights
FrontierPriceFrom $104Free CancellationRating
5.8
3,122 reviews
Search Frontier flights
Alaska AirlinesPriceFrom $142Free CancellationRating
8.0
11,199 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $165Free CancellationRating
7.2
11,033 reviews
Search American Airlines flights
Hawaiian AirlinesPriceFrom $168Free CancellationRating
7.8
2,794 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $176Free CancellationRating
7.4
8,996 reviews
Search United Airlines flights
SouthwestPriceFrom $195Free CancellationRating
8.0
4,235 reviews
Search Southwest flights
DeltaPriceFrom $223Free CancellationRating
7.9
7,995 reviews
Search Delta flights

  • Alaska Airlines Flights From Chicago to San Diego

    Alaska Airlines flies from Chicago to San Diego around 4 times per week, with 11,199 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 $229 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 $458, however, with flight time and availability significantly affecting the price. Southwest (8.0/10 from 4,235 user reviews) flies into San Diego from Chicago 24 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
La Mesa
Imperial Beach
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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