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$89+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Diego are usually found in June or January, booked 42 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$196
(Cheapflightsfares)

One-way from

$89
(Frontier)

Popular in

March

Cheapest in

June

Average price

$298

Good round-trip deal

$420 or less

Good one-way deal

$255 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. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/18:03 pmMDW - SAN
1 stop6h 10mFrontier
Mon 5/56:25 amSAN - MDW
1 stop6h 23mFrontier
Deal found 4/14$196
This Southwest deal was found by Cheapflights users on 4/14. 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.
Sat 5/248:05 amMDW - SAN
Nonstop4h 20mSouthwest
Tue 5/275:55 pmSAN - MDW
Nonstop4h 00mSouthwest
Deal found 4/14$237
This Delta deal was found by Cheapflights users on 4/14. 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 6/75:25 pmMDW - SAN
1 stop7h 15mDelta
Sat 6/1410:15 pmSAN - MDW
1 stop8h 26mDelta
Deal found 4/14$257
This Mytrip deal was found by Cheapflights users on 4/13. 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.
Mon 6/309:12 amMDW - SAN
2 stops35h 14mMultiple Airlines
Sun 7/66:15 amSAN - MDW
2 stops25h 26mMultiple Airlines
Deal found 4/13$396

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 April 15, 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

Thu 5/1

8:03 pm-12:13 am

1 stop6h 10m

San Diego

Mon 5/5

6:25 am-2:48 pm

1 stop6h 23m

$196

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 5/24

8:05 am-10:25 am

Nonstop4h 20m

San Diego

Tue 5/27

5:55 pm-11:55 pm

Nonstop4h 00m

$237

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 6/7

5:25 pm-10:40 pm

1 stop7h 15m

San Diego

Sat 6/14

6:20 am-5:12 pm

1 stop8h 52m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 6/30

9:12 am-6:26 pm

2 stops35h 14m

San Diego

Sun 7/6

6:15 am-9:41 am

2 stops25h 26m

$396

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 4/29

12:19 pm-6:28 pm

1 stop8h 09m

$89

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 5/22

8:20 pm-6:56 am

1 stop12h 36m

$110

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 5/24

8:05 am-10:25 am

Nonstop4h 20m

$119

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sun 5/4

6:15 am-7:34 am

1 stop27h 19m

$123

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 5/28

1:08 pm-6:08 pm

1 stop7h 00m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
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 eDreams the most. eDreams 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 April 11, 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 42 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 April 15, 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 31% 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 March 30, 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. Friday 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 April 15, 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
4,278 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
7,917 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
734 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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 3 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 $196. Other airlines that can offer you cheap pricing are Southwest, from $247, and Delta, from $257. These flights start at 46% 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 $89 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $110 and Southwest from $119 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 $190. While the most popular route (Chicago Midway - San Diego) can be booked for $215 on average our data indicates $407 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
Lemon Grove
National City
Imperial Beach
La Mesa
Alpine
Poway
Santee
Coronado
Borrego Springs

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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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$196FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$204Average$449FlexibilityNo cancel feeOn-time63%

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