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$81+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
May 3 — May 101
Sun 5/3
Sun 5/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Diego are usually found in February or January, booked 81 days in advance, depart on a Sunday or Thursday and return on a Wednesday

Cheap 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 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:35 pm
MDW
-
SAN
1 stop25h 54m
Frontier
Mon 5/46:25 am
SAN
-
MDW
1 stop29h 47m
Frontier
Deal found 3/30$191
This Southwest deal was found by Cheapflights users on 4/1. 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.
Mon 4/275:55 pm
MDW
-
SAN
1 stop7h 00m
Southwest
Wed 4/299:35 pm
SAN
-
MDW
1 stop5h 25m
Southwest
Deal found 4/1$195
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 5/84:05 pm
MDW
-
SAN
2 stops7h 20m
Southwest
Mon 5/116:30 am
SAN
-
MDW
1 stop6h 45m
Southwest
Deal found 4/1$196
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:20 am
MDW
-
SAN
1 stop13h 28m
Frontier
Tue 4/287:15 am
SAN
-
MDW
2 stops12h 59m
Frontier
Deal found 3/30$198
This Expedia deal was found by Cheapflights users on 3/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:11 pm
MDW
-
SAN
1 stop8h 33m
Frontier
Thu 4/167:52 am
SAN
-
MDW
1 stop12h 30m
Frontier
Deal found 3/30$200
This Southwest deal was found by Cheapflights users on 4/1. 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.
Wed 4/2910:10 am
MDW
-
SAN
2 stops7h 35m
Southwest
Sat 5/26:25 am
SAN
-
MDW
2 stops8h 25m
Southwest
Deal found 4/1$201
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:25 am
MDW
-
SAN
1 stop17h 19m
Frontier
Fri 5/81:38 pm
SAN
-
MDW
2 stops19h 26m
Frontier
Deal found 4/2$202
This Frontier deal was found by Cheapflights users on 3/31. 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.
Thu 4/234:15 pm
MDW
-
SAN
1 stop10h 01m
Frontier
Mon 4/278:38 am
SAN
-
MDW
1 stop11h 17m
Frontier
Deal found 3/31$205
This Southwest deal was found by Cheapflights users on 4/1. 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.
Thu 4/236:40 am
MDW
-
SAN
Nonstop4h 15m
Southwest
Wed 4/2910:40 pm
SAN
-
MDW
Nonstop3h 55m
Southwest
Deal found 4/1$206
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:30 pm
MDW
-
SAN
1 stop26h 54m
Frontier
Sun 4/266:56 pm
SAN
-
MDW
1 stop24h 59m
Frontier
Deal found 3/31$214
This CheapOair deal was found by Cheapflights users on 4/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:15 pm
MDW
-
SAN
1 stop9h 56m
Frontier
Fri 4/2411:01 am
SAN
-
MDW
1 stop8h 49m
Frontier
Deal found 4/2$215

Find 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 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$191
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$298

Good round-trip deal

$297 or less

Good one-way deal

$153 or less
Provider with most accurate pricing for Chicago Midway-San Diego flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San Diego flights.
Search Deals
From Chicago Midway to San Diego
Search Deals
One-way flight from Chicago Midway to San Diego
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Diego.
Search Deals
Price to beat on a one-way flight from Chicago Midway to San Diego.
Search Deals

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 3, 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

Tue 5/5

7:16 pm-11:38 pm

1 stop6h 22m

San Diego

Sat 5/9

10:25 pm-10:00 am

1 stop9h 35m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 4/25

10:10 am-4:25 pm

2 stops8h 15m

San Diego

Sat 5/2

6:25 am-2:20 pm

1 stop5h 55m

$258

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Sat 5/30

1:22 pm-6:01 pm

1 stop6h 39m

San Diego

Mon 6/8

10:17 pm-9:14 am

1 stop8h 57m

$287

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 5/15

5:25 pm-7:45 pm

Nonstop4h 20m

San Diego

Sun 5/17

10:40 pm-4:35 am

Nonstop3h 55m

$297
Quickest round-trip

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 5/1

6:40 am-8:55 am

Nonstop4h 15m

San Diego

Fri 5/8

10:40 pm-4:35 am

Nonstop3h 55m

$297

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 4/30

10:25 am-3:00 pm

1 stop6h 35m

San Diego

Sun 5/3

9:35 pm-5:00 am

1 stop5h 25m

$317

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 5/28

6:40 am-8:55 am

Nonstop4h 15m

San Diego

Mon 6/1

10:40 pm-4:35 am

Nonstop3h 55m

$347

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 8/4

6:00 am-9:30 am

1 stop5h 30m

San Diego

Mon 8/10

5:50 pm-11:45 pm

Nonstop3h 55m

$353

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 8/28

6:15 am-8:20 am

Nonstop4h 05m

San Diego

Sun 8/30

9:35 pm-5:50 am

1 stop6h 15m

$357

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Tue 7/28

1:49 pm-8:36 pm

1 stop8h 47m

San Diego

Tue 8/4

10:17 pm-9:08 am

1 stop8h 51m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 April 2, 2026.

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 80 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $153). Flying from Chicago Midway Airport to San Diego in June is currently the most expensive (average of $295). 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 3, 2026.

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 evening, which can drop the price by up to 41% 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 28, 2026.

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. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago Midway Airport to San Diego?

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Diego trip
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on SAN

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

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 April 3, 2026.
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
4,339 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,339 reviews
Southwest
8.0
Very good
4,339 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,003 reviews
Southwest
8.0
Very good
4,339 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

  • 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 6h 22m. Fly via Delta or Southwest to get the fastest option. Airlines will cover a distance of 1725 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $151. Another airline that can offer you cheap pricing is Southwest. These flights start at 54% 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 $118. While the most popular route (Chicago Midway - San Diego) can be booked for $175 on average, our data indicates $340 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $153). Flying from Chicago Midway Airport to San Diego in June is currently the most expensive (average of $295). 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
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove

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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 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$151Average$308FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$336FlexibilityNo cancel feeOn-time63%

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