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$77+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
nov 1 — nov 81
sáb 11/1
sáb 11/8
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Diego are usually found in January or October, booked 52 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

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 outubro 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Southwest)

One-way from

$77
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$307

Good round-trip deal

$227 or less

Good one-way deal

$114 or less
Provider with most accurate pricing for Chicago Midway-San Diego flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San Diego flights.
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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. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in October 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 outubro 2, 2025.

This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 11/82:57 pmMDW - SAN
1 stop7h 27mFrontier
seg 11/176:25 amSAN - MDW
1 stop8h 36mFrontier
Deal found 9/29$154
This Mytrip deal was found by Cheapflights users on 10/1. 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.
sáb 11/82:57 pmMDW - SAN
1 stop7h 27mFrontier
sáb 11/155:28 pmSAN - MDW
1 stop16h 02mFrontier
Deal found 10/1$155
This Booking.com deal was found by Cheapflights users on 9/30. 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.
qui 10/3012:30 pmMDW - SAN
1 stop13h 20mFrontier
qua 11/56:41 amSAN - MDW
1 stop26h 49mFrontier
Deal found 9/30$156
This Southwest deal was found by Cheapflights users on 9/29. 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.
qua 10/227:10 amMDW - SAN
Nonstop4h 20mSouthwest
qua 10/296:30 amSAN - MDW
Nonstop4h 05mSouthwest
Deal found 9/29$163
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 11/911:23 amMDW - SAN
1 stop9h 51mFrontier
qui 11/136:25 amSAN - MDW
1 stop12h 19mFrontier
Deal found 9/29$169
This Booking.com deal was found by Cheapflights users on 10/1. 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.
seg 10/206:24 pmMDW - SAN
1 stop7h 26mFrontier
dom 11/25:41 amSAN - MDW
1 stop26h 49mFrontier
Deal found 10/1$171
This Southwest deal was found by Cheapflights users on 10/1. 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.
qua 10/227:10 amMDW - SAN
Nonstop4h 20mSouthwest
ter 10/286:30 amSAN - MDW
Nonstop4h 05mSouthwest
Deal found 10/1$173
This Southwest deal was found by Cheapflights users on 10/2. 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.
ter 12/236:05 amMDW - SAN
Nonstop4h 25mSouthwest
ter 12/306:35 amSAN - MDW
Nonstop4h 05mSouthwest
Deal found 10/2$177
This CheapOair deal was found by Cheapflights users on 10/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 11/211:21 amMDW - SAN
1 stop9h 08mFrontier
seg 11/36:25 amSAN - MDW
1 stop9h 24mFrontier
Deal found 10/1$190
This Southwest deal was found by Cheapflights users on 9/30. 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.
sex 10/244:30 pmMDW - SAN
1 stop7h 00mSouthwest
sáb 10/256:55 amSAN - MDW
Nonstop4h 05mSouthwest
Deal found 9/30$195

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 outubro 2, 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

sáb 10/18

1:50 pm-4:05 pm

Nonstop4h 15m

San Diego

ter 10/21

6:30 am-12:35 pm

Nonstop4h 05m

$198

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

qui 1/29

6:10 am-11:50 am

1 stop7h 40m

San Diego

dom 2/1

3:30 pm-11:45 pm

1 stop6h 15m

$216

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

qui 1/22

6:10 am-10:35 am

1 stop6h 25m

San Diego

qui 1/29

2:00 pm-9:15 pm

1 stop5h 15m

$216

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

seg 1/5

7:10 pm-11:25 pm

1 stop6h 15m

San Diego

seg 1/12

7:30 am-4:35 pm

2 stops7h 05m

$217

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

sex 10/31

2:25 pm-4:40 pm

Nonstop4h 15m

San Diego

dom 11/2

5:35 am-11:40 am

Nonstop4h 05m

$237

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

qua 11/12

1:55 pm-4:15 pm

Nonstop4h 20m

San Diego

seg 11/17

6:30 am-12:35 pm

Nonstop4h 05m

$237

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

qua 2/18

6:00 am-11:05 am

1 stop7h 05m

San Diego

sáb 2/21

10:30 am-8:00 pm

2 stops7h 30m

$240

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

qua 10/15

11:55 am-2:10 pm

Nonstop4h 15m

San Diego

dom 11/2

7:35 pm-1:30 am

Nonstop3h 55m

$250

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

sex 10/24

4:30 pm-9:30 pm

1 stop7h 00m

San Diego

sáb 10/25

1:50 pm-11:25 pm

1 stop7h 35m

$256

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

dom 11/2

5:15 am-9:15 am

1 stop6h 00m

San Diego

sex 11/7

9:20 pm-5:05 am

1 stop5h 45m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 20 results
1
2

Compare providers for flights from Midway to San Diego

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Diego in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San Diego flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Diego flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Diego flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San Diego flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Diego flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 September 26, 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 52 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 outubro 2, 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 22% 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 September 28, 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.

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

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 outubro 2, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Diego, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,155 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Chicago Midway Airport to San Diego?

    There are many flights that can get you from Chicago Midway Airport to San Diego in 4h 15m. Fly via Southwest to get the fastest option. Airlines will cover a distance of 1725 mi. Generally, flights for this route are nonstop.

  • 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 $108. Another airline that can offer you cheap pricing is Southwest. These flights start at 70% lower than the current average price 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago Midway - San Diego) can be booked for $163 on average, our data indicates $257 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
Coronado
La Mesa
Poway
Lemon Grove
Imperial Beach
National City

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Alternative routes for Midway to San Diego

See prices for flight routes from nearby airports that may be better suited for you.
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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 outubro 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$201FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$188Average$417FlexibilityNo cancel feeOn-time63%

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