HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Diego

$84+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Jul 11 — Jul 181
Fri 7/11
Fri 7/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to San Diego with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 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 July 6, 2025.

Round-trip from

$171
(Southwest)

One-way from

$84
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$350

Good round-trip deal

$277 or less

Good one-way deal

$118 or less
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. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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

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 July 6, 2025.

This Southwest deal was found by Cheapflights users on 7/3. 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 8/167:25 pmMDW - SAN
Nonstop4h 10mSouthwest
Sat 8/237:30 amSAN - MDW
Nonstop4h 00mSouthwest
Deal found 7/3$171
This Priceline deal was found by Cheapflights users on 7/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/172:44 pmMDW - SAN
1 stop11h 08mFrontier
Tue 7/228:00 amSAN - MDW
1 stop7h 03mFrontier
Deal found 7/5$187
This Delta deal was found by Cheapflights users on 7/4. 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.
Mon 8/1812:43 pmMDW - SAN
1 stop8h 43mDelta
Thu 8/216:20 amSAN - MDW
1 stop9h 17mDelta
Deal found 7/4$257

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 July 6, 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

Sat 8/16

7:25 pm-9:35 pm

Nonstop4h 10m

San Diego

Sat 8/23

7:30 am-1:30 pm

Nonstop4h 00m

$171

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 7/17

2:44 pm-11:52 pm

1 stop11h 08m

San Diego

Tue 7/22

8:00 am-5:03 pm

1 stop7h 03m

$187

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 8/18

12:43 pm-7:26 pm

1 stop8h 43m

San Diego

Mon 8/25

10:30 pm-9:36 am

1 stop9h 06m

$257

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 9/29

7:03 pm-11:45 pm

1 stop6h 42m

$84

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 8/6

1:35 pm-3:45 pm

Nonstop4h 10m

$86

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 7/17

2:44 pm-11:52 pm

1 stop11h 08m

$88

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Fri 8/8

12:43 pm-7:56 pm

1 stop9h 13m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

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 27, 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 July 6, 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 20% 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 July 6, 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.

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 July 6, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Diego, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,259 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Comfort

8.0

Overall

8.0

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
4,259 reviews
Southwest
8.0
Very good
4,259 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Comfort

8.0

Overall

8.0

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
7,964 reviews
Southwest
8.0
Very good
4,259 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Comfort

8.0

Overall

8.0

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
3,278 reviews
Southwest
8.0
Very good
4,259 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Comfort

8.0

Overall

8.0

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 1 inbound flight 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 $171. Other airlines that can offer you cheap pricing are Frontier, from $187, and Delta, from $257. These flights start at 55% 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 $86 on Southwest. Other airlines that offer cheap prices include Frontier from $88 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 $105. While the most popular route (Chicago Midway - San Diego) can be booked for $171 on average our data indicates $227 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
Coronado
National City
Lemon Grove
Imperial Beach
La Mesa
Poway
Alpine
Santee

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to San Diego

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
Midway to Las Vegas flights
O'Hare Intl to San Diego flights
O'Hare Intl to Ontario flights
O'Hare Intl to Santa Ana flights
Midway to San Francisco flights
O'Hare Intl to Burbank flights
Midway to Los Angeles flights
O'Hare Intl to Reno flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Oakland flights
O'Hare Intl to San Jose flights
Rockford to Las Vegas flights
O'Hare Intl to Sacramento flights
O'Hare Intl to Fresno flights
Midway to Santa Ana flights
Midway to San Jose flights
Midway to Reno flights
Midway to Long Beach flights
O'Hare Intl to Long Beach flights
Midway to Palm Springs flights
Midway to Ontario flights
Midway to Sacramento flights
Midway to Oakland flights
O'Hare Intl to Monterey flights
Midway to Fresno flights
Midway to Burbank flights
O'Hare Intl to Medford flights
O'Hare Intl to Santa Rosa flights
O'Hare Intl to San Luis Obispo flights
O'Hare Intl to Santa Barbara flights
Midway to Medford flights
O'Hare Intl to Arcata flights
O'Hare Intl to Bakersfield flights
O'Hare Intl to Tijuana flights
O'Hare Intl to Redding flights
Midway to Tijuana flights
O'Hare Intl to Yuma flights
Midway to Mexicali flights
O'Hare Intl to Mexicali flights
O'Hare Intl to Merced flights
O'Hare Intl to Mammoth Lakes flights

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 July 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$211FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$223Average$437FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.