$122+ Cheap flights from Midway (MDW) to San Diego (SAN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Oct 30 — Nov 61
Round-trip
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 February or April, booked 36 days in advance, depart on a Sunday or Saturday and return on a Saturday
Cheap flight deals from Midway to San Diego
Cheapest
Best
Last-minute
One-way
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 September 30, 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 September 30, 2026.
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.
Sat 10/247:05 pm -
Nonstop4h 25m
Sat 10/316:40 am -
Nonstop3h 50m
Deal found 9/30![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 9/27. 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.
Tue 10/276:55 am -
1 stop5h 50m
Wed 10/2810:40 pm -
Nonstop3h 50m
Deal found 9/27![Southwest logo]()
$263
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.
Tue 10/276:55 am -
1 stop5h 50m
Tue 11/38:25 am -
1 stop6h 20m
Deal found 9/29![Southwest logo]()
$272
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:29 am -
1 stop6h 51m
Sat 10/316:25 am -
1 stop8h 22m
Deal found 9/30![Delta logo]()
$277
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.
Sat 10/316:00 am -
2 stops8h 00m
Sat 11/76:30 pm -
1 stop9h 25m
Deal found 9/30![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 9/26. 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 10/3112:50 pm -
2 stops7h 15m
Tue 11/108:20 am -
2 stops7h 05m
Deal found 9/26![Southwest logo]()
$287
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.
Sat 11/76:20 pm -
Nonstop4h 30m
Sat 11/146:40 am -
2 stops8h 25m
Deal found 9/30![Southwest logo]()
$292
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:20 pm -
2 stops13h 37m
Sat 11/146:25 am -
2 stops15h 22m
Deal found 9/30![Frontier logo]()
$295
Best flights from Midway to San DiegoDiscover carefully curated flight deals from Midway to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 30, 2026.
Discover carefully curated flight deals from Midway to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 30, 2026.
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.
Wed 11/1110:10 am -
1 stop7h 20m
Sun 11/1510:40 pm -
Nonstop3h 45m
Deal found 9/29![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/27. 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.
Fri 10/235:09 pm -
1 stop8h 15m
Tue 11/36:15 am -
1 stop7h 02m
Deal found 9/27![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 9/25. 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.
Tue 12/88:55 pm -
Nonstop4h 25m
Fri 12/116:35 am -
Nonstop4h 00m
Deal found 9/25![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 9/25. 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 10/177:05 pm -
Nonstop4h 25m
Sat 10/2410:20 am -
2 stops8h 20m
Deal found 9/25![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/28. 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 10/295:15 am -
1 stop6h 05m
Sun 11/15:20 pm -
1 stop5h 45m
Deal found 9/28![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/25. 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 11/197:05 am -
1 stop6h 45m
Sat 11/219:25 pm -
1 stop6h 15m
Deal found 9/25![Southwest logo]()
$375
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.
Thu 11/1910:10 am -
Nonstop4h 25m
Thu 11/194:05 pm -
Nonstop3h 55m
Deal found 9/29![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 9/27. 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 10/146:05 am -
1 stop6h 10m
Mon 10/1910:15 pm -
1 stop5h 30m
Deal found 9/27![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 9/28. 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 10/99:25 pm -
Nonstop4h 25m
Sun 10/1110:40 pm -
Nonstop3h 50m
Deal found 9/28![Southwest logo]()
$455
Last-minute flights from Midway to San DiegoDiscover last-minute flight deals from Midway to San Diego. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Diego. Data last updated September 30, 2026 and is based on user searches.
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.
Sat 10/247:05 pm -
Nonstop4h 25m
Sat 10/316:40 am -
Nonstop3h 50m
Deal found 9/30![Southwest logo]()
$257
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:29 am -
1 stop6h 51m
Sat 10/316:25 am -
1 stop8h 22m
Deal found 9/30![Delta logo]()
$277
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:29 am -
1 stop6h 51m
Tue 11/312:38 pm -
1 stop7h 55m
Deal found 9/29![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 9/28. 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 10/245:10 am -
1 stop6h 00m
Sun 11/16:35 am -
Nonstop4h 00m
Deal found 9/28![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 9/27. 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.
Tue 10/276:55 am -
1 stop5h 50m
Wed 10/2810:40 pm -
Nonstop3h 50m
Deal found 9/27![Southwest logo]()
$263
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.
Tue 10/276:55 am -
1 stop5h 50m
Tue 11/38:25 am -
1 stop6h 20m
Deal found 9/29![Southwest logo]()
$272
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.
Wed 10/283:05 pm -
1 stop5h 45m
Thu 10/296:55 pm -
Nonstop3h 55m
Deal found 9/29![Southwest logo]()
$303
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.
Sat 10/316:00 am -
2 stops8h 00m
Sat 11/76:30 pm -
1 stop9h 25m
Deal found 9/30![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 9/26. 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 10/3112:50 pm -
2 stops7h 15m
Tue 11/108:20 am -
2 stops7h 05m
Deal found 9/26![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/27. 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 10/316:00 am -
1 stop8h 35m
Wed 11/48:20 am -
2 stops7h 05m
Deal found 9/27![Southwest logo]()
$302
One-way flights from Midway to San DiegoSearch for one-way flight options from Midway to San Diego. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
Search for one-way flight options from Midway to San Diego. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:16 am -
2 stops43h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$122
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.
Wed 11/412:27 pm -
2 stops13h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$124
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.
Tue 10/276:25 am -
Nonstop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$129
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:20 pm -
2 stops13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$135
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:30 pm -
2 stops24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$137
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:20 pm -
2 stops37h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$138
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.
Sat 10/316:05 am -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$139
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.
Tue 11/36:42 pm -
2 stops23h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$140
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:28 pm -
2 stops13h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 9/27. 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.
Tue 11/1010:05 am -
2 stops7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Southwest logo]()
$144
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 September 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Southwest) |
One-way from | $122 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $357 |
Good round-trip deal | $297 or less |
Good one-way deal | $169 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 7,457,451 searches. Data last updated September 30, 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
Cheapest round-trip
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Sat 10/31
6:04 am-11:13 am
1 stop7h 09m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$139
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Thu 12/10
8:55 pm-11:20 pm
Nonstop4h 25m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$169
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Thu 10/29
5:15 am-9:20 am
1 stop6h 05m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$174
Quickest round-trip
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Fri 10/23
2:55 pm-5:15 pm
Nonstop4h 20m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Mon 10/26
9:25 pm-11:50 pm
Nonstop4h 25m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Sat 10/31
6:00 am-12:00 pm
2 stops8h 00m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$184
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Thu 12/17
9:20 pm-11:45 pm
Nonstop4h 25m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$187
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Wed 11/25
9:15 pm-11:55 pm
Nonstop4h 40m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$187
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Mon 11/23
6:00 am-1:08 pm
1 stop9h 08m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$197
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Wed 10/7
6:25 am-8:50 am
Nonstop4h 25m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$198
Showing 1-10 of 19 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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.
MDW-SAN
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?
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 35 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to San Diego (average of $207). Flying from Chicago Midway Airport to San Diego in December is currently the most expensive (average of $451). 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 September 30, 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 29% 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 26, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to San Diego flight should consider departing on Tuesday at noon 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.
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
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 September 30, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Diego, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
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?
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Midway and San Diego flights
Browse other Midway and San Diego flight options. Last updated on September 30, 2026.
Other flights from Midway
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Other flights to San Diego
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Top airline flying from Midway to San Diego
Discover the top airline 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 7,457,451 searches. Data last updated September 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$353 | FlexibilityNo cancel fee | On-time63% |