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$106+ Cheap flights from Midway (MDW) to San Diego (SAN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Diego are usually found in January or April, booked 55 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Midway to San Diego

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Diego (SAN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$186
(Southwest)

One-way from

$106
(Southwest)

Popular in

March

Cheapest in

January

Average price

$349

Good round-trip deal

$282 or less

Good one-way deal

$168 or less
From Chicago Midway to San Diego
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One-way flight from Chicago Midway to San Diego
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Highest demand for flights based on searches. 8% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago Midway to San Diego.
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Price to beat on a one-way flight from Chicago Midway to San Diego.
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Find flight deals from Midway to San Diego

Cheapest flights from Midway to San Diego
Explore the most affordable flight options available from Midway to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/228:50 pmMDW - SAN
Nonstop4h 15mSouthwest
Tue 8/268:10 amSAN - MDW
Nonstop4h 00mSouthwest
Deal found 6/10$186
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/231:08 pmMDW - SAN
1 stop6h 53mDelta
Tue 8/2610:30 pmSAN - MDW
1 stop8h 46mDelta
Deal found 6/10$257
This Booking.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/142:44 pmMDW - SAN
1 stop21h 08mFrontier
Sun 8/176:25 amSAN - MDW
1 stop27h 16mFrontier
Deal found 6/12$260
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/49:12 amMDW - SAN
2 stops40h 17mMultiple Airlines
Sun 7/136:15 amSAN - MDW
2 stops25h 26mMultiple Airlines
Deal found 6/11$362

Cheapflights Fare Finder

Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Diego that are best for you.

Fly from

Midway

Fly to

San Diego

Route

Depart

Return

Price

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 8/22

8:50 pm-11:05 pm

Nonstop4h 15m

San Diego

Tue 8/26

8:10 am-2:10 pm

Nonstop4h 00m

$186

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 8/23

1:08 pm-6:01 pm

1 stop6h 53m

San Diego

Tue 8/26

10:30 pm-9:16 am

1 stop8h 46m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 8/14

2:44 pm-9:52 am

1 stop21h 08m

San Diego

Sun 8/17

6:25 am-11:41 am

1 stop27h 16m

$260

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 7/4

9:12 am-11:29 pm

2 stops40h 17m

San Diego

Sun 7/13

6:15 am-9:41 am

2 stops25h 26m

$362

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 8/7

8:50 pm-11:05 pm

Nonstop4h 15m

$106

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 6/30

6:25 am-6:26 pm

1 stop14h 01m

$108

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 8/28

11:00 am-4:59 pm

1 stop7h 59m

$122

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 7/26

4:22 pm-9:35 pm

1 stop7h 13m

$129

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 7/31

8:14 pm-6:10 pm

1 stop23h 56m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

The best insider tips for Chicago Midway Airport to San Diego flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Diego trip
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
SAN

Take the free San Diego Flyer shuttle to connect between Terminals 1 and 2 and the Old Town Transit Center.

Read more about SANby Blane Bachelor
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on SAN

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Midway to San Diego

Have a flexible travel schedule? Discover the best time to fly to San Diego from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to San Diego

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Diego. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to San Diego, you should look to book at least 55 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to San Diego?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $286). Flying from Chicago Midway Airport to San Diego in March is currently the most expensive (average of $366). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to SAN?

Find hourly flight availability from Midway to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

When flying from Chicago Midway Airport to San Diego, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 32% versus a flight at noon.

What is the cheapest day to fly from Chicago Midway Airport to San Diego?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Diego. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to San Diego flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in San Diego by month

Plan your trip to San Diego by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Diego ranges from 0.0 - 2.3 inches per month. February is typically the wettest month, when rainfall can reach 2.3 in. July is typically the driest time to visit San Diego when rainfall is around 0.0 in.

Temperature in San Diego by month

Plan your trip to San Diego by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Diego, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 57.2 F).

Reviews of airlines servicing San Diego

Get insights into the airlines that provide service to San Diego. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Diego. Reviews last updated June 12, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Chicago to San Diego have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

Find useful and relevant information for your journey from Midway to San Diego. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San Diego from Chicago Midway?

    San Diego (SAN), located 2.6 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to San Diego. 2 airlines have flights to San Diego from Chicago Midway on a regular basis. Booking flights from Chicago Midway to San Diego should not be difficult; the airport handles an average of 2 inbound flights from Chicago Midway per day.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Diego round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to San Diego round-trip from $186. Other airlines that can offer you cheap pricing are Delta, from $257, and Frontier, from $260. These flights start at 51% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Diego one-way?

    One-way options have recently been found by users for as low as $106 on Southwest. Other airlines that offer cheap prices include Frontier from $122 and Delta from $129 one-way.

  • What are the cheapest flights from Chicago Midway Airport to San Diego?

    Looking at all options, your cheapest flight can be booked for $128. While the most popular route (Chicago Midway - San Diego) can be booked for $161 on average our data indicates $285 when flying from Chicago Midway Airport to San Diego.

  • Can I find deals for flights from Midway to San Diego that include hotel bookings?

    Yes. In addition to deals on Midway to San Diego flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to San Diego?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San Diego.

  • Can I find deals for business class flights from Midway to San Diego?

    Yes. Cheapflights offers flight deals from Midway to San Diego by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San Diego?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $286). Flying from Chicago Midway Airport to San Diego in March is currently the most expensive (average of $366). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
El Cajon
Chula Vista
National City
Imperial Beach
La Mesa
Alpine
Lemon Grove
Poway
Santee
Coronado

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Alternative routes for Midway to San Diego

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Top 2 airlines flying from Midway to San Diego

Discover the top 2 airlines that operate flights from Midway to San Diego. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$203FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$436FlexibilityNo cancel feeOn-time63%

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