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Cheap flights from Chicago to San Diego from $52

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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Find the cheapest flights from Chicago to San Diego

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to San Diego that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San Diego.

Cheap last minute flights

Planning a quick getaway from Chicago to San Diego? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Diego, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San Diego

Find recent round-trip train or bus tickets from Chicago to San Diego.

All round-trip flight deals to San Diego

The cheapest plane tickets to San Diego found on KAYAK recently.
12:43 pm - 7:06 pmMDW-SAN
8h 23m1 stop
8:45 am - 8:14 pmSAN-MDW
9h 29m1 stop
$107Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
12:43 pm - 7:06 pmMDW-SAN
8h 23m1 stop
8:45 am - 8:14 pmSAN-MDW
9h 29m1 stop
$108Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
1:47 pm - 11:44 pmSAN-ORD
7h 57m1 stop
Thu, Jan 16 - Thu, Jan 23
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
$123Spirit Airlines
Find Deal
Thu, Jan 9 - Mon, Jan 13
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
5:01 pm - 5:31 amSAN-ORD
10h 30m1 stop
$126Spirit Airlines
Find Deal
Thu, Jan 9 - Mon, Jan 13
6:36 pm - 7:06 pmORD-SAN
26h 30m1 stop
5:01 pm - 5:31 amSAN-ORD
10h 30m1 stop
Thu, Jan 9 - Mon, Jan 13
9:30 am - 2:38 pmMDW-SAN
7h 08m1 stop
10:23 pm - 8:50 amSAN-MDW
8h 27m1 stop
$300Delta
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Wed, Dec 18 - Wed, Dec 25
6:00 am - 1:16 pmMDW-SAN
9h 16m1 stop
7:25 am - 4:12 pmSAN-MDW
6h 47m1 stop
$320Delta
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Sat, Jan 11 - Sat, Jan 18
3:20 pm - 5:55 pmMDW-SAN
4h 35mnonstop
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
$352Southwest
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Sat, Jan 18 - Sat, Jan 25
1:05 pm - 5:45 pmMDW-SAN
6h 40m1 stop
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
$361Southwest
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Sat, Jan 18 - Sat, Jan 25
6:20 am - 12:07 pmMDW-SAN
7h 47m1 stop
$52Frontier
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Tue, Dec 17
8:15 am - 1:29 pmMDW-SAN
7h 14m1 stop
$53Frontier
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Tue, Jan 14
6:50 am - 11:48 amORD-SAN
6h 58m1 stop
$53Frontier
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Tue, Feb 25
1:39 pm - 11:54 pmORD-SAN
12h 15m1 stop
$64Spirit Airlines
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Wed, Feb 12
10:47 pm - 8:58 amORD-SAN
12h 11m1 stop
$68Spirit Airlines
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Thu, Feb 6
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
$176American Airlines
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Tue, Dec 31
8:40 am - 11:20 amMDW-SAN
4h 40mnonstop
$176Southwest
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Sun, Jan 19
9:15 am - 5:05 pmMDW-SAN
9h 50m2 stops
$190Southwest
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Sat, Jan 18
1:15 pm - 3:48 pmORD-SAN
4h 33mnonstop
$196United Airlines
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Sat, Jan 18
7:42 pm - 10:17 pmORD-SAN
4h 35mnonstop
$215United Airlines
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Tue, Dec 24
9:37 pm - 11:49 pmMDW-SAN
28h 12m1 stop
6:25 am - 12:13 amSAN-MDW
15h 48m1 stop
$178Frontier
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Mon, Dec 2 - Wed, Dec 11
7:00 am - 6:26 pmMDW-SAN
13h 26m1 stop
6:25 am - 12:13 amSAN-MDW
15h 48m1 stop
$261Frontier
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Fri, Nov 29 - Thu, Dec 5
8:27 pm - 6:40 amORD-SAN
12h 13m1 stop
7:15 pm - 5:30 amSAN-ORD
8h 15m1 stop
$321Spirit Airlines
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Mon, Dec 2 - Wed, Dec 11
11:51 am - 6:40 amORD-SAN
20h 49m2 stops
7:15 pm - 5:30 amSAN-ORD
8h 15m1 stop
$334Spirit Airlines
Find Deal
Fri, Nov 29 - Thu, Dec 5
8:30 pm - 1:15 amORD-SAN
6h 45m1 stop
8:45 am - 12:22 amSAN-ORD
13h 37m1 stop
$677United Airlines
Find Deal
Sun, Dec 1 - Wed, Dec 4
8:30 pm - 1:15 amORD-SAN
6h 45m1 stop
10:45 am - 12:22 amSAN-ORD
11h 37m2 stops
$701United Airlines
Find Deal
Sun, Dec 1 - Wed, Dec 4
9:09 pm - 11:36 pmORD-SAN
4h 27mnonstop
10:36 pm - 4:45 amSAN-ORD
4h 09mnonstop
$751American Airlines
Find Deal
Mon, Dec 2 - Thu, Dec 5
8:10 pm - 10:35 pmMDW-SAN
4h 25mnonstop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$760Southwest
Find Deal
Mon, Dec 2 - Wed, Dec 4
8:10 pm - 10:35 pmMDW-SAN
4h 25mnonstop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$777Southwest
Find Deal
Sun, Dec 1 - Wed, Dec 4
5:00 am - 12:30 pmORD-SAN
9h 30m2 stops
12:28 pm - 11:49 pmSAN-ORD
9h 21m2 stops
$873American Airlines
Find Deal
Sun, Dec 1 - Wed, Dec 4
3:20 pm - 5:55 pmMDW-SAN
4h 35mnonstop
2:35 pm - 8:25 pmSAN-MDW
3h 50mnonstop
$352Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 25
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
$352American Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
1:28 pm - 7:38 pmSAN-ORD
4h 10mnonstop
$355American Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
10:05 am - 12:36 pmORD-SAN
4h 31mnonstop
1:28 pm - 7:38 pmSAN-ORD
4h 10mnonstop
$391American Airlines
Find Deal
Sun, Jan 19 - Sat, Jan 25
4:20 pm - 6:54 pmORD-SAN
4h 34mnonstop
10:30 pm - 4:35 amSAN-ORD
4h 05mnonstop
$410United Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
9:07 pm - 11:40 pmORD-SAN
4h 33mnonstop
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
$411American Airlines
Find Deal
Wed, Jan 1 - Tue, Jan 7
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
5:10 pm - 11:00 pmSAN-MDW
3h 50mnonstop
$412Southwest
Find Deal
Sun, Jan 19 - Wed, Jan 22
7:50 pm - 10:22 pmORD-SAN
4h 32mnonstop
2:14 pm - 8:25 pmSAN-ORD
4h 11mnonstop
$442United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24
10:15 am - 12:37 pmORD-SAN
4h 22mnonstop
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
$633Alaska Airlines
Find Deal
Tue, Dec 24 - Mon, Dec 30
10:15 am - 12:37 pmORD-SAN
4h 22mnonstop
10:39 pm - 4:42 amSAN-ORD
4h 03mnonstop
$673Alaska Airlines
Find Deal
Tue, Dec 24 - Sun, Dec 29

Spirit Airlines flights from Chicago to San Diego

Our best Spirit Airlines deals on Chicago to San Diego flight tickets
Spirit Airlines
Jan 9
ORD10:47 pmChicago O'Hare Intl
12h 11m
1 stop
SAN8:58 amSan Diego
Jan 13
SAN7:26 pmSan Diego
8h 05m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Jan 9
ORD10:47 pmChicago O'Hare Intl
12h 11m
1 stop
SAN8:58 amSan Diego
Jan 13
SAN5:01 pmSan Diego
10h 30m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Jan 9
ORD10:47 pmChicago O'Hare Intl
12h 11m
1 stop
SAN8:58 amSan Diego
Jan 13
SAN7:26 pmSan Diego
8h 05m
1 stop
ORD5:31 amChicago O'Hare Intl

Frontier flights from Chicago to San Diego

Our best Frontier deals on Chicago to San Diego flight tickets
Frontier
Jan 9
MDW12:43 pmChicago Midway
8h 23m
1 stop
SAN7:06 pmSan Diego
Jan 13
SAN8:45 amSan Diego
9h 29m
1 stop
MDW8:14 pmChicago Midway
Frontier
Feb 25
ORD6:50 amChicago O'Hare Intl
6h 58m
1 stop
SAN11:48 amSan Diego
Mar 3
SAN8:08 pmSan Diego
6h 57m
1 stop
ORD5:05 amChicago O'Hare Intl
Frontier
Jan 13
MDW7:15 amChicago Midway
19h 01m
1 stop
SAN12:16 amSan Diego
Jan 14
SAN6:25 amSan Diego
15h 48m
1 stop
MDW12:13 amChicago Midway

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 April, then departing from Chicago during the month May is also very affordable. Most momondo users find prices during this month for around $373.

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 Tuesday. Travelers who choose to depart for San Diego on a Tuesday will often find tickets for as low as $374. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $469. 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 in the evening when flights can be purchased for as low as $389. Flights at noon are often more expensive with an average ticket price of $451.

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?

Most flyers found that booking tickets 55 days in advance of their planned departure date is the best time to get cheap flights to San Diego. During this timeframe, flight prices are around $407. However, in the past 72 hours, people saw flights from Chicago for as low as $308.

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 70% 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 November 2024, prices for Chicago to San Diego flights are approximately 19% 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

$52

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 $52. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $107.
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)

  • 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
FrontierPriceFrom $105Free CancellationRating
6.1
3,523 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $107Free CancellationRating
6.3
8,172 reviews
Search Spirit Airlines flights
DeltaPriceFrom $171Free CancellationRating
8.0
8,730 reviews
Search Delta flights
SouthwestPriceFrom $201Free CancellationRating
8.1
4,979 reviews
Search Southwest flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $245Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $329Free CancellationRating
8.0
9,481 reviews
Search Alaska Airlines flights
  • Southwest Flights From Chicago to San Diego

    Southwest flies from Chicago to San Diego around 6 times per week, with 4,979 momondo users rating the airline 8.1/10. The cheapest Southwest deal from Chicago to San Diego in the last 72 hours was $201 (round-trip), much lower than the average airfare cost of $443 for Southwest flights on this route.

  • Alaska Airlines Flights From Chicago to San Diego

    $329 is the best Alaska Airlines flight deal from Chicago to San Diego found on momondo over the last 72 hours. The average Alaska Airlines ticket price found was closer to $693, however, with flight time and availability significantly affecting the price. Alaska Airlines (8.0/10 from 9,481 user reviews) flies into San Diego from Chicago 12 times in an average week so prices can vary.


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.


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