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

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
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
Southwest Logo
7:45 am - 10:10 amMDW-SAN
4h 25mnonstop
Southwest Logo
6:30 am - 12:35 pmSAN-MDW
4h 05mnonstop
$167Southwest
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Sun, Dec 7 - Tue, Dec 9
Southwest Logo
7:50 pm - 10:20 pmMDW-SAN
4h 30mnonstop
Southwest Logo
7:30 am - 4:35 pmSAN-MDW
7h 05m2 stops
$170Southwest
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Tue, Jan 13 - Tue, Jan 20
Southwest Logo
5:55 pm - 10:15 pmMDW-SAN
6h 20m1 stop
Southwest Logo
1:05 pm - 9:05 pmSAN-MDW
6h 00m1 stop
$172Southwest
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Sat, Feb 14 - Tue, Feb 17
Southwest Logo
8:25 am - 1:30 pmMDW-SAN
7h 05m1 stop
Southwest Logo
2:20 pm - 10:30 pmSAN-MDW
6h 10m1 stop
$174Southwest
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Wed, Feb 11 - Sun, Feb 15
Southwest Logo
6:10 am - 8:50 amMDW-SAN
4h 40mnonstop
Southwest Logo
2:20 pm - 10:30 pmSAN-MDW
6h 10m1 stop
$175Southwest
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Thu, Feb 12 - Sun, Feb 15
Frontier Logo
8:05 am - 11:51 pmMDW-SAN
17h 46m1 stop
Frontier Logo
1:03 pm - 11:45 amSAN-MDW
20h 42m1 stop
$176Frontier
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Thu, Dec 11 - Wed, Jan 7
Southwest Logo
7:50 pm - 10:20 pmMDW-SAN
4h 30mnonstop
Southwest Logo
6:45 am - 12:40 pmSAN-MDW
3h 55mnonstop
$177Southwest
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Thu, Jan 8 - Sun, Jan 11
Frontier Logo
3:10 pm - 9:57 amMDW-SAN
20h 47m2 stops
Frontier Logo
1:03 pm - 11:45 amSAN-MDW
20h 42m1 stop
$178Frontier
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Wed, Dec 31 - Wed, Jan 7

Southwest flights from Chicago Midway Airport to San Diego

Our best Southwest deals on Chicago Midway Airport to San Diego flight tickets
Southwest
Dec 24
MDW1:55 pmChicago Midway
4h 20m
SAN4:15 pmSan Diego
Dec 31
SAN3:15 pmSan Diego
5h 40m
1 stop
MDW10:55 pmChicago Midway
$163
Find similar
Southwest
Jan 10
MDW7:40 pmChicago Midway
4h 30m
SAN10:10 pmSan Diego
Jan 17
SAN7:30 pmSan Diego
7h 35m
1 stop
MDW5:05 amChicago Midway
$165
Find similar
Southwest
Dec 7
MDW7:45 amChicago Midway
4h 25m
SAN10:10 amSan Diego
Dec 9
SAN6:30 amSan Diego
4h 05m
MDW12:35 pmChicago Midway
$167
Find similar

Frontier flights from Chicago Midway Airport to San Diego

Our best Frontier deals on Chicago Midway Airport to San Diego flight tickets
Frontier
Dec 11
MDW8:05 amChicago Midway
17h 46m
1 stop
SAN11:51 pmSan Diego
Jan 7
SAN1:03 pmSan Diego
20h 42m
1 stop
MDW11:45 amChicago Midway
$176
Find similar
Frontier
Dec 31
MDW3:10 pmChicago Midway
20h 47m
2 stops
SAN9:57 amSan Diego
Jan 7
SAN1:03 pmSan Diego
20h 42m
1 stop
MDW11:45 amChicago Midway
$178
Find similar
Frontier
Jan 4
MDW10:50 pmChicago Midway
22h 25m
1 stop
SAN7:15 pmSan Diego
Jan 7
SAN1:03 pmSan Diego
20h 42m
1 stop
MDW11:45 amChicago Midway
$183
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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 November 17, 2025.
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

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

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

MDW - SAN

MDWSAN

Chicago Midway

Sun 12/7

7:45 am-10:10 am

Nonstop4h 25m

San Diego

Tue 12/9

6:30 am-12:35 pm

Nonstop4h 05m

$167

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 1/13

7:50 pm-10:20 pm

Nonstop4h 30m

San Diego

Tue 1/20

7:30 am-4:35 pm

2 stops7h 05m

$170

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 2/14

5:55 pm-10:15 pm

1 stop6h 20m

San Diego

Tue 2/17

1:05 pm-9:05 pm

1 stop6h 00m

$172

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 2/11

8:25 am-1:30 pm

1 stop7h 05m

San Diego

Sun 2/15

2:20 pm-10:30 pm

1 stop6h 10m

$174

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 2/12

6:10 am-8:50 am

Nonstop4h 40m

San Diego

Sun 2/15

2:20 pm-10:30 pm

1 stop6h 10m

$175

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 12/11

8:05 am-11:51 pm

1 stop17h 46m

San Diego

Wed 1/7

1:03 pm-11:45 am

1 stop20h 42m

$176

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 1/8

7:50 pm-10:20 pm

Nonstop4h 30m

San Diego

Sun 1/11

6:45 am-12:40 pm

Nonstop3h 55m

$177

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 12/31

3:10 pm-9:57 am

2 stops20h 47m

San Diego

Wed 1/7

1:03 pm-11:45 am

1 stop20h 42m

$178

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 cheapest month to fly to San Diego?

If you are unable to visit San Diego during the month of January, then departing from Chicago Midway Airport during the month August is also very affordable. Most momondo users find prices during this month for around $314.

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 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 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 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 $366 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 $181 on momondo.

What cabin class options are available on Chicago Midway to San Diego flights?

There is only 1 cabin class available to choose from on Chicago Midway 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 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 November 2025, prices for Chicago Midway Airport to San Diego flights are approximately 11% 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

$208

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 Midway Airport in the past 72 hours is $208. The best round-trip flight deal from Chicago Midway Airport to San Diego found on momondo in the last 72 hours is $237.
The fastest flight from Chicago Midway Airport to San Diego takes 4h 20m
Direct flights go from Chicago Midway Airport to San Diego every day.
There is 1 airport near San Diego: San Diego (SAN)
Search flight deals

  • 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 20m, 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 $108Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
SouthwestPriceFrom $195Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Diego

    Southwest operates around 27 flights from Chicago Midway Airport to San Diego every week. The average price of these flights found in the last 72 hours has been $413, but momondo users have found Southwest deals from Chicago Midway Airport to San Diego from as low as $195 round-trip. Southwest has been scored 8.0/10 in 4,244 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
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?

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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Wed 12/17
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