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$79+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Feb 3 — Feb 101
1 adult, Economy
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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 February, booked 79 days in advance, depart on a Wednesday or Thursday and return on a Tuesday
Cheap flight deals from Midway to San Diego
Cheapest flights from Midway to San DiegoExplore 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 January 4, 2026.
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 January 4, 2026.
This Southwest deal was found by Cheapflights users on 1/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/77:40 pmMDW - SAN
Nonstop4h 30mSouthwest
Tue 2/107:30 amSAN - MDW
2 stops7h 05mSouthwest
Deal found 1/4![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 1/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:40 pmMDW - SAN
Nonstop4h 30mSouthwest
Wed 2/253:25 pmSAN - MDW
1 stop5h 25mSouthwest
Deal found 1/4![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 1/3. 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 1/247:40 pmMDW - SAN
Nonstop4h 30mSouthwest
Sat 1/317:25 amSAN - MDW
2 stops7h 20mSouthwest
Deal found 1/3![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 1/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:26 pmMDW - SAN
1 stop8h 53mFrontier
Sun 3/83:16 pmSAN - MDW
1 stop29h 29mFrontier
Deal found 1/1![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/17:30 amMDW - SAN
1 stop9h 41mFrontier
Fri 2/66:30 amSAN - MDW
2 stops13h 49mFrontier
Deal found 1/3![Frontier logo]()
$166
This Southwest deal was found by Cheapflights users on 1/1. 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 1/308:15 amMDW - SAN
Nonstop4h 35mSouthwest
Wed 2/410:05 amSAN - MDW
Nonstop4h 00mSouthwest
Deal found 1/1![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 1/3. 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.
Wed 2/115:05 amMDW - SAN
1 stop6h 10mSouthwest
Sat 2/147:15 amSAN - MDW
Nonstop4h 00mSouthwest
Deal found 1/3![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 1/3. 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.
Mon 2/27:50 pmMDW - SAN
Nonstop4h 30mSouthwest
Sat 2/77:25 amSAN - MDW
Nonstop3h 55mSouthwest
Deal found 1/3![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 1/3. 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 1/247:40 pmMDW - SAN
Nonstop4h 30mSouthwest
Sun 1/256:45 amSAN - MDW
Nonstop3h 55mSouthwest
Deal found 1/3![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 1/2. 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.
Mon 2/168:58 pmMDW - SAN
1 stop25h 26mFrontier
Mon 2/236:25 amSAN - MDW
2 stops11h 22mFrontier
Deal found 1/2![Frontier logo]()
$176
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 January 4, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $160 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $236 |
Good round-trip deal | $212 or less |
Good one-way deal | $173 or less |
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 January 4, 2026.
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 2/7
7:40 pm-10:10 pm
Nonstop4h 30m
San Diego
Tue 2/10
7:30 am-4:35 pm
2 stops7h 05m
$160
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 1/24
7:40 pm-10:10 pm
Nonstop4h 30m
San Diego
Sat 1/31
7:25 am-4:45 pm
2 stops7h 20m
$163
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 3/7
8:55 pm-11:25 pm
Nonstop4h 30m
San Diego
Wed 3/11
8:35 pm-5:45 am
1 stop7h 10m
$164
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 1/24
7:40 pm-10:10 pm
Nonstop4h 30m
San Diego
Sun 1/25
6:45 am-12:40 pm
Nonstop3h 55m
$175
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Wed 3/11
5:10 pm-7:40 pm
Nonstop4h 30m
San Diego
Sun 3/15
6:30 am-12:35 pm
Nonstop4h 05m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Wed 2/11
5:05 am-9:15 am
1 stop6h 10m
San Diego
Sat 2/14
9:20 am-5:10 pm
1 stop5h 50m
$180
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 2/5
2:05 pm-7:35 pm
2 stops7h 30m
San Diego
Sun 2/8
6:25 am-12:25 pm
Nonstop4h 00m
$212
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 2/20
5:15 am-10:10 am
1 stop6h 55m
San Diego
Mon 2/23
8:45 pm-5:05 am
1 stop6h 20m
$217
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sun 2/22
3:10 pm-5:40 pm
Nonstop4h 30m
San Diego
Sat 2/28
7:15 am-1:15 pm
Nonstop4h 00m
$219
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 2/19
8:00 am-10:35 am
Nonstop4h 35m
San Diego
Thu 2/19
6:30 pm-12:25 am
Nonstop3h 55m
$222
Showing 1-10 of 22 results
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 January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Diego flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-San Diego flight deals on Cheapflights vs. eDreams >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 January 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 76 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $130). Flying from Chicago Midway Airport to San Diego in June is currently the most expensive (average of $296). 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 January 4, 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 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 December 27, 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. Sunday 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
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
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 January 4, 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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
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.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsEl Cajon
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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.
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 January 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$389 | FlexibilityNo cancel fee | On-time63% |