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Cheap flights from Chicago Midway Airport to San Diego from $124

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 Midway Airport to San Diego departing on 6/9. 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 Midway Airport to San Diego

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:40 pm - 10:55 pm
MDW
-
SAN
4h 15mnonstop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$252Southwest
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
6:45 am - 9:00 am
MDW
-
SAN
4h 15mnonstop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$257Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
12:05 pm - 5:10 pm
MDW
-
SAN
7h 05m
1 stop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$262Southwest
Tue, Jun 9 - Tue, Jun 9
Southwest Logo
6:45 am - 9:00 am
MDW
-
SAN
4h 15mnonstop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$277Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
5:45 am - 7:50 am
MDW
-
SAN
4h 05mnonstop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$282Southwest
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
6:10 am - 10:50 am
MDW
-
SAN
6h 40m
1 stop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$287Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
4:00 pm - 7:35 pm
MDW
-
SAN
5h 35m
1 stop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$292Southwest
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
5:25 pm - 7:45 pm
MDW
-
SAN
4h 20mnonstop
Southwest Logo
10:40 pm - 4:35 am
SAN
-
MDW
3h 55mnonstop
$297Southwest
Fri, May 29 - Tue, Jun 2
Southwest Logo
9:10 pm - 11:25 pm
MDW
-
SAN
4h 15mnonstop
Southwest Logo
10:40 pm - 4:40 am
SAN
-
MDW
4h 00mnonstop
$302Southwest
Sun, May 31 - Sat, Jun 6
Southwest Logo
8:40 pm - 10:55 pm
MDW
-
SAN
4h 15mnonstop
Southwest Logo
6:20 am - 12:25 pm
SAN
-
MDW
4h 05mnonstop
$307Southwest
Sat, Jun 6 - Sun, Jun 7

Frontier flights from Chicago Midway Airport to San Diego

Our best Frontier deals on Chicago Midway Airport to San Diego flight tickets
Frontier
Jun 2
MDW12:27 pmChicago Midway
22h 15m
2 stops
SAN8:42 amSan Diego
Jun 6
SAN6:25 amSan Diego
8h 17m
1 stop
MDW4:42 pmChicago Midway
$316
Frontier
May 26
MDW3:07 pmChicago Midway
29h 23m
1 stop
SAN6:30 pmSan Diego
Jun 2
SAN6:25 amSan Diego
37h 37m
2 stops
MDW10:02 pmChicago Midway
$414
Frontier
May 28
MDW6:00 amChicago Midway
28h 42m
2 stops
SAN8:42 amSan Diego
Jun 1
SAN6:25 amSan Diego
29h 47m
1 stop
MDW2:12 pmChicago Midway
$425

Southwest flights from Chicago Midway Airport to San Diego

Our best Southwest deals on Chicago Midway Airport to San Diego flight tickets
Southwest
Jun 6
MDW8:40 pmChicago Midway
4h 15m
SAN10:55 pmSan Diego
Jun 9
SAN10:40 pmSan Diego
4h 00m
MDW4:40 amChicago Midway
$252
Southwest
Jun 2
MDW6:45 amChicago Midway
4h 15m
SAN9:00 amSan Diego
Jun 6
SAN10:40 pmSan Diego
4h 00m
MDW4:40 amChicago Midway
$257
Southwest
Jun 9
MDW12:05 pmChicago Midway
7h 05m
1 stop
SAN5:10 pmSan Diego
Jun 9
SAN10:40 pmSan Diego
4h 00m
MDW4:40 amChicago Midway
$262

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 May 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Diego that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 6/6

8:40 pm-10:55 pm

Nonstop4h 15m

San Diego

Tue 6/9

10:40 pm-4:40 am

Nonstop4h 00m

$252

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 6/2

6:45 am-9:00 am

Nonstop4h 15m

San Diego

Sat 6/6

10:40 pm-4:40 am

Nonstop4h 00m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 6/9

12:05 pm-5:10 pm

1 stop7h 05m

San Diego

Tue 6/9

10:40 pm-4:40 am

Nonstop4h 00m

$262

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 6/2

6:45 am-9:00 am

Nonstop4h 15m

San Diego

Sat 6/6

10:40 pm-4:40 am

Nonstop4h 00m

$277
Quickest round-trip

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 6/4

5:45 am-7:50 am

Nonstop4h 05m

San Diego

Tue 6/9

10:40 pm-4:40 am

Nonstop4h 00m

$282

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 6/2

6:10 am-10:50 am

1 stop6h 40m

San Diego

Sat 6/6

10:40 pm-4:40 am

Nonstop4h 00m

$287

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 6/4

4:00 pm-7:35 pm

1 stop5h 35m

San Diego

Tue 6/9

10:40 pm-4:40 am

Nonstop4h 00m

$292

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 5/29

5:25 pm-7:45 pm

Nonstop4h 20m

San Diego

Tue 6/2

10:40 pm-4:35 am

Nonstop3h 55m

$297

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sun 5/31

9:10 pm-11:25 pm

Nonstop4h 15m

San Diego

Sat 6/6

10:40 pm-4:40 am

Nonstop4h 00m

$302

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 6/6

8:40 pm-10:55 pm

Nonstop4h 15m

San Diego

Sun 6/7

6:20 am-12:25 pm

Nonstop4h 05m

$307

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 Midway Airport 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 Midway Airport 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 February, then departing from Chicago Midway Airport during the month January is also very affordable. Most momondo users find prices during this month for around $240.

What is the cheapest day to depart on your flight to San Diego?

The cheapest day to depart from Chicago Midway Airport to San Diego is on a Saturday. Travelers who choose to depart for San Diego on a Saturday will often find tickets for as low as $282. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $340. 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 $279. Flights in the afternoon are often more expensive with an average ticket price of $311.

What is the cheapest Chicago Midway to San Diego flight route?

Fly from Chicago Midway to San Diego for the best Chicago Midway - San Diego flight prices

How far in advance should I book a flight from Chicago Midway Airport to San Diego?

You are more likely to see cheaper flights to San Diego from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $324 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 Midway Airport for as low as $226 on momondo.

Can stopping save me money on Chicago Midway Airport to San Diego flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San Diego.

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

As of May 2026, prices for Chicago Midway Airport to San Diego flights are approximately 262% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to San Diego

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Diego according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San Diego (MDW to SAN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Diego

Best Price Found

$188

Fastest flight time

4h 05m

Direct flights

Every day

Airports in San Diego

1 airport
The best one-way flight to San Diego from Chicago Midway Airport in the past 72 hours is $188. The best round-trip flight deal from Chicago Midway Airport to San Diego found on momondo in the last 72 hours is $322.
The fastest flight from Chicago Midway Airport to San Diego takes 4h 05m
Direct flights go from Chicago Midway Airport to San Diego every day.
There is 1 airport in San Diego. From Chicago Midway Airport there are direct flights to San Diego (SAN).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San Diego

  • How far is Chicago Midway to San Diego by plane?

    San Diego is 1723.1 mi away from Chicago Midway. Flights usually cover this in 4h 05m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to San Diego Airport?

    Prices for flights from Chicago Midway Airport to San Diego Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San Diego Airport?

  • How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport to San Diego Airport.

  • What documentation or ID do you need to fly to San Diego Airport?

    The necessary travel and health documents for your San Diego Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San Diego?

  • What is the most popular airline from Chicago Midway Airport to San Diego?

Best airlines flying from Chicago Midway Airport to San Diego

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Diego with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $151Free CancellationRating
5.6
2,951 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,299 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Diego

    Southwest operates around 25 flights from Chicago Midway Airport to San Diego every week. The average price of these flights found in the last 72 hours has been $336, but momondo users have found Southwest deals from Chicago Midway Airport to San Diego from as low as $177 round-trip. Southwest has been scored 8.0/10 in 4,299 reviews.

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
Poway
San Ysidro
La Mesa
Imperial Beach
Borrego Springs
Lemon Grove
Alpine
Santee

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Diego?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Diego from Chicago.

Can I find flights from Chicago to San Diego with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to San Diego from Chicago with this policy.

How can momondo help me find flights from Chicago to San Diego?

Once you have performed a search for Chicago to San Diego flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.
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