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Cheap flights from Chicago to San Diego from $44

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 1/22. 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.
8:23 pm - 12:05 pmORD-SAN
17h 42m1 stop
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
Mon, Jan 20 - Wed, Jan 22
8:23 pm - 11:54 amORD-SAN
17h 31m1 stop
7:26 pm - 5:31 amSAN-ORD
8h 05m1 stop
Mon, Jan 13 - Wed, Jan 22
8:23 pm - 12:05 pmORD-SAN
17h 42m1 stop
12:55 pm - 5:25 pmSAN-ORD
26h 30m1 stop
$104Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 5
6:20 am - 5:33 pmORD-SAN
13h 13m1 stop
12:05 pm - 1:01 amSAN-ORD
10h 56m1 stop
$105Frontier
Find Deal
Sat, Feb 8 - Sat, Feb 15
7:15 am - 11:31 amMDW-SAN
6h 16m1 stop
2:32 pm - 12:17 amSAN-MDW
7h 45m1 stop
$106Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 5
5:45 pm - 8:04 pmORD-SAN
4h 19mnonstop
1:34 pm - 7:38 pmSAN-ORD
4h 04mnonstop
$237American Airlines
Find Deal
Tue, Feb 18 - Sat, Feb 22
8:45 pm - 11:15 pmMDW-SAN
4h 30mnonstop
6:20 am - 12:10 pmSAN-MDW
3h 50mnonstop
$237Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22
5:45 pm - 8:04 pmORD-SAN
4h 19mnonstop
6:40 am - 12:31 pmSAN-ORD
3h 51mnonstop
$238American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
2:39 pm - 9:10 pmORD-SAN
8h 31m1 stop
2:14 pm - 8:25 pmSAN-ORD
4h 11mnonstop
$247United Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
5:10 pm - 9:55 pmMDW-SAN
6h 45m1 stop
4:55 pm - 10:45 pmSAN-MDW
3h 50mnonstop
$283Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22
1:39 pm - 10:18 pmORD-SAN
10h 39m1 stop
$44Spirit Airlines
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Wed, Jan 22
8:15 am - 1:32 pmMDW-SAN
7h 17m1 stop
$54Frontier
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Wed, Jan 29
4:20 pm - 7:00 pmORD-SAN
4h 40mnonstop
$119United Airlines
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Sat, Feb 22
8:45 pm - 11:15 pmMDW-SAN
4h 30mnonstop
$119Southwest
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Sat, Feb 15
12:44 pm - 9:05 pmMDW-SAN
10h 21m1 stop
$140Delta
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Wed, Jan 29
5:00 pm - 10:48 pmORD-SAN
7h 48m1 stop
$140Delta
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Sat, Mar 15
7:55 pm - 10:30 pmORD-SAN
4h 35mnonstop
$164United Airlines
Find Deal
Sat, Jan 25
1:15 pm - 7:35 pmMDW-SAN
8h 20m2 stops
$170Southwest
Find Deal
Sat, Feb 22
10:05 am - 12:36 pmORD-SAN
4h 31mnonstop
$193American Airlines
Find Deal
Wed, Feb 5
6:50 am - 9:17 amORD-SAN
4h 27mnonstop
$236American Airlines
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Thu, Apr 10
1:07 pm - 11:54 pmORD-SAN
12h 47m1 stop
8:45 am - 7:07 pmSAN-ORD
8h 22m1 stop
$244Frontier
Find Deal
Thu, Jan 2 - Mon, Feb 3
8:41 pm - 9:16 amMDW-SAN
14h 35m1 stop
2:32 pm - 12:17 amSAN-MDW
7h 45m1 stop
$246Frontier
Find Deal
Thu, Jan 2 - Tue, Feb 4
8:55 pm - 10:12 pmORD-SAN
27h 17m2 stops
4:21 pm - 5:31 amSAN-ORD
11h 10m1 stop
$334Spirit Airlines
Find Deal
Thu, Jan 2 - Tue, Feb 4
8:55 pm - 10:12 pmORD-SAN
27h 17m2 stops
2:10 pm - 5:31 amSAN-ORD
13h 21m2 stops
$349Spirit Airlines
Find Deal
Thu, Jan 2 - Tue, Feb 4
4:50 pm - 7:12 pmORD-SAN
4h 22mnonstop
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
$657American Airlines
Find Deal
Thu, Jan 2 - Tue, Feb 4
10:05 am - 12:41 pmORD-SAN
4h 36mnonstop
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
$697American Airlines
Find Deal
Sun, Dec 29 - Tue, Jan 14
4:20 pm - 6:54 pmORD-SAN
4h 34mnonstop
12:40 pm - 11:59 pmSAN-ORD
9h 19m1 stop
$700United Airlines
Find Deal
Sun, Dec 29 - Tue, Jan 14
7:42 pm - 10:17 pmORD-SAN
4h 35mnonstop
7:00 am - 1:11 pmSAN-ORD
4h 11mnonstop
$722United Airlines
Find Deal
Thu, Jan 2 - Sat, Jan 11
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
7:00 am - 12:55 pmSAN-MDW
3h 55mnonstop
$877Southwest
Find Deal
Tue, Dec 31 - Fri, Jan 3
9:45 am - 12:10 pmMDW-SAN
4h 25mnonstop
12:20 pm - 8:45 pmSAN-MDW
6h 25m1 stop
$886Southwest
Find Deal
Tue, Dec 31 - Fri, Jan 3
8:45 pm - 11:15 pmMDW-SAN
4h 30mnonstop
4:55 pm - 10:45 pmSAN-MDW
3h 50mnonstop
$237Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22
5:45 pm - 8:04 pmORD-SAN
4h 19mnonstop
1:34 pm - 7:38 pmSAN-ORD
4h 04mnonstop
$237American Airlines
Find Deal
Tue, Feb 18 - Sat, Feb 22
5:45 pm - 8:04 pmORD-SAN
4h 19mnonstop
6:40 am - 12:31 pmSAN-ORD
3h 51mnonstop
$238American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
5:45 pm - 8:04 pmORD-SAN
4h 19mnonstop
1:34 pm - 7:38 pmSAN-ORD
4h 04mnonstop
$239American Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
5:45 pm - 8:10 pmORD-SAN
4h 25mnonstop
6:40 am - 12:48 pmSAN-ORD
4h 08mnonstop
$312American Airlines
Find Deal
Tue, Jan 14 - Sat, Jan 18
4:20 pm - 7:00 pmORD-SAN
4h 40mnonstop
10:25 pm - 4:20 amSAN-ORD
3h 55mnonstop
$328United Airlines
Find Deal
Sat, Feb 15 - Sat, Feb 22
3:20 pm - 5:55 pmMDW-SAN
4h 35mnonstop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$337Southwest
Find Deal
Sat, Jan 25 - Mon, Jan 27
1:15 pm - 3:48 pmORD-SAN
4h 33mnonstop
7:00 am - 1:11 pmSAN-ORD
4h 11mnonstop
$402United Airlines
Find Deal
Wed, Jan 15 - Sat, Jan 18
9:07 pm - 11:34 pmORD-SAN
4h 27mnonstop
10:30 am - 4:43 pmSAN-ORD
4h 13mnonstop
$663Alaska Airlines
Find Deal
Sat, Mar 29 - Mon, Apr 7
9:07 pm - 11:34 pmORD-SAN
4h 27mnonstop
9:59 am - 4:05 pmSAN-ORD
4h 06mnonstop
$693Alaska Airlines
Find Deal
Sun, Mar 30 - Sat, Apr 5

Frontier flights from Chicago to San Diego

Our best Frontier deals on Chicago to San Diego flight tickets
Frontier
Feb 3
ORD8:23 pmChicago O'Hare Intl
17h 42m
1 stop
SAN12:05 pmSan Diego
Feb 5
SAN12:55 pmSan Diego
26h 30m
1 stop
ORD5:25 pmChicago O'Hare Intl
Frontier
Feb 8
ORD6:20 amChicago O'Hare Intl
13h 13m
1 stop
SAN5:33 pmSan Diego
Feb 15
SAN12:05 pmSan Diego
10h 56m
1 stop
ORD1:01 amChicago O'Hare Intl
Frontier
Feb 3
MDW7:15 amChicago Midway
6h 16m
1 stop
SAN11:31 amSan Diego
Feb 5
SAN2:32 pmSan Diego
7h 45m
1 stop
MDW12:17 amChicago Midway

Spirit Airlines flights from Chicago to San Diego

Our best Spirit Airlines deals on Chicago to San Diego flight tickets
Spirit Airlines
Feb 10
ORD1:39 pmChicago O'Hare Intl
10h 39m
1 stop
SAN10:18 pmSan Diego
Feb 17
SAN7:41 pmSan Diego
8h 26m
1 stop
ORD6:07 amChicago O'Hare Intl
Spirit Airlines
Jan 23
ORD10:47 pmChicago O'Hare Intl
12h 11m
1 stop
SAN8:58 amSan Diego
Feb 1
SAN7:26 pmSan Diego
8h 05m
1 stop
ORD5:31 amChicago O'Hare Intl
Spirit Airlines
Jan 22
ORD1:39 pmChicago O'Hare Intl
10h 39m
1 stop
SAN10:18 pmSan Diego
Jan 27
SAN7:26 pmSan Diego
8h 05m
1 stop
ORD5:31 amChicago O'Hare Intl

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 $379. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $471. 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 $398. Flights at noon are often more expensive with an average ticket price of $457.

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 44 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 $421. However, in the past 72 hours, people saw flights from Chicago for as low as $288.

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 63% 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 December 2024, prices for Chicago to San Diego flights are approximately 0% 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

$44

Fastest flight time

4h 19m

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 $44. The best round-trip flight deal from Chicago to San Diego found on momondo in the last 72 hours is $97.
The fastest flight from Chicago to San Diego takes 4h 19m
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 19m.

  • 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 $103Free CancellationRating
6.3
8,104 reviews
Search Spirit Airlines flights
FrontierPriceFrom $105Free CancellationRating
6.0
3,459 reviews
Search Frontier flights
DeltaPriceFrom $171Free CancellationRating
8.0
8,556 reviews
Search Delta flights
SouthwestPriceFrom $201Free CancellationRating
8.1
4,731 reviews
Search Southwest flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $247Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $329Free CancellationRating
8.0
9,573 reviews
Search Alaska Airlines flights
  • Southwest Flights From Chicago to San Diego

    Southwest flies from Chicago to San Diego around 11 times per week, with 4,731 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 $480 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 $704, however, with flight time and availability significantly affecting the price. Alaska Airlines (8.0/10 from 9,575 user reviews) flies into San Diego from Chicago 22 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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