$159+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Aug 17 — Aug 241
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 January, booked 80 days in advance, depart on a Sunday or Tuesday and return on a Wednesday
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 July 18, 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 July 18, 2026.
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 8/201:25 pm
MDW
- SAN
1 stop6h 49m
Delta
Sat 8/296:15 am
SAN
- MDW
1 stop7h 23m
Delta
Deal found 7/16![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 8/123:10 pm
MDW
- SAN
1 stop5h 45m
Southwest
Tue 8/1810:40 pm
SAN
- MDW
1 stop6h 55m
Southwest
Deal found 7/14![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 7/17. 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 8/221:45 pm
MDW
- SAN
1 stop5h 25m
Southwest
Mon 8/2410:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/17![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 7/17. 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 8/312:50 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 9/76:45 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 7/17![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2910:15 am
MDW
- SAN
2 stops7h 10m
Southwest
Sat 9/510:40 pm
SAN
- MDW
1 stop7h 00m
Southwest
Deal found 7/15![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/14. 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.
Tue 8/113:10 pm
MDW
- SAN
1 stop5h 45m
Southwest
Wed 8/1910:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/14![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 7/16. 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 8/152:20 pm
MDW
- SAN
1 stop6h 05m
Southwest
Sat 8/2210:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/16![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 7/15. 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 9/186:15 pm
MDW
- SAN
1 stop5h 55m
Southwest
Thu 9/245:50 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 7/15![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 7/14. 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.
Wed 8/1210:54 am
MDW
- SAN
1 stop8h 11m
Delta
Tue 8/1812:32 pm
SAN
- MDW
1 stop8h 04m
Delta
Deal found 7/14![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:05 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 8/175:50 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 7/13![Southwest logo]()
$302
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 July 18, 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 July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/17. 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 8/316:15 am
MDW
- SAN
Nonstop4h 05m
Southwest
Tue 9/112:20 pm
SAN
- MDW
1 stop6h 45m
Southwest
Deal found 7/17![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 9/242:00 pm
MDW
- SAN
1 stop8h 37m
Delta
Sun 9/2710:25 pm
SAN
- MDW
1 stop9h 25m
Delta
Deal found 7/15![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 7/15. 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 8/216:15 am
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 8/2410:40 pm
SAN
- MDW
1 stop6h 55m
Southwest
Deal found 7/15![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/16. 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 8/152:20 pm
MDW
- SAN
1 stop6h 05m
Southwest
Sat 8/229:10 am
SAN
- MDW
1 stop9h 05m
Southwest
Deal found 7/16![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 7/15. 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 8/107:25 pm
MDW
- SAN
1 stop6h 10m
Delta
Wed 8/2612:32 pm
SAN
- MDW
1 stop8h 04m
Delta
Deal found 7/15![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 7/17. 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 10/223:45 pm
MDW
- SAN
1 stop6h 20m
Southwest
Sun 10/2510:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/17![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 7/16. 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.
Sun 10/256:30 am
MDW
- SAN
Nonstop4h 25m
Southwest
Sun 11/16:35 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 7/16![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:10 am
MDW
- SAN
1 stop6h 05m
Southwest
Mon 8/1010:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/13![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 7/16. 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 11/62:30 pm
MDW
- SAN
1 stop6h 25m
Southwest
Sun 11/1510:40 pm
SAN
- MDW
Nonstop3h 45m
Southwest
Deal found 7/16![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/14. 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.
Tue 8/48:25 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Sat 8/810:40 pm
SAN
- MDW
1 stop6h 10m
Southwest
Deal found 7/14![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:00 am
MDW
- SAN
2 stops11h 10m
Southwest
Sun 8/309:35 pm
SAN
- MDW
1 stop6h 15m
Southwest
Deal found 7/13![Southwest logo]()
$358
Last-minute flights from Midway to San DiegoDiscover last-minute flight deals from Midway to San Diego. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Diego. Data last updated July 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/14. 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.
Tue 8/113:10 pm
MDW
- SAN
1 stop5h 45m
Southwest
Wed 8/1910:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/14![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 8/123:10 pm
MDW
- SAN
1 stop5h 45m
Southwest
Tue 8/1810:40 pm
SAN
- MDW
1 stop6h 55m
Southwest
Deal found 7/14![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 7/14. 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.
Wed 8/125:10 pm
MDW
- SAN
1 stop7h 50m
Delta
Tue 8/2512:32 pm
SAN
- MDW
1 stop8h 04m
Delta
Deal found 7/14![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 7/16. 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 8/152:20 pm
MDW
- SAN
1 stop6h 05m
Southwest
Sat 8/2210:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/16![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:05 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 8/175:50 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 7/13![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 8/201:25 pm
MDW
- SAN
1 stop6h 49m
Delta
Sat 8/296:15 am
SAN
- MDW
1 stop7h 23m
Delta
Deal found 7/16![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 7/14. 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.
Fri 8/212:50 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 8/248:45 pm
SAN
- MDW
1 stop7h 00m
Southwest
Deal found 7/14![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/17. 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 8/221:45 pm
MDW
- SAN
1 stop5h 25m
Southwest
Mon 8/2410:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 7/17![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2910:15 am
MDW
- SAN
2 stops7h 10m
Southwest
Sat 9/510:40 pm
SAN
- MDW
1 stop7h 00m
Southwest
Deal found 7/15![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/17. 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 8/312:50 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Mon 9/76:45 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 7/17![Southwest logo]()
$291
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 July 18, 2026.
Search for one-way flight options from Midway to San Diego. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:45 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 7/13![Southwest logo]()
$159
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/101:25 pm
MDW
- SAN
1 stop6h 49m
Delta
Deal found 7/13![Delta logo]()
$160
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:30 am
MDW
- SAN
2 stops6h 55m
Southwest
Deal found 7/13![Southwest logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:06 am
MDW
- SAN
2 stops30h 37m
Frontier
Deal found 7/13![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/1711:06 am
MDW
- SAN
2 stops29h 44m
Frontier
Deal found 7/16![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:03 pm
MDW
- SAN
2 stops23h 17m
Frontier
Deal found 7/13![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:17 pm
MDW
- SAN
2 stops23h 26m
Frontier
Deal found 7/14![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:11 pm
MDW
- SAN
2 stops27h 57m
Frontier
Deal found 7/14![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:50 am
MDW
- SAN
2 stops29h 00m
Frontier
Deal found 7/13![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 9/117:25 am
MDW
- SAN
2 stops15h 23m
Frontier
Deal found 7/15![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/2011:50 am
MDW
- SAN
2 stops29h 00m
Frontier
Deal found 7/16![Frontier logo]()
$171
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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Delta) |
One-way from | $159 (Southwest) |
Popular in | December |
Cheapest in | February |
Average price | $392 |
Good round-trip deal | $358 or less |
Good one-way deal | $178 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 July 18, 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 - SAN
MDWSAN
Chicago Midway
Mon 8/31
6:15 am-8:20 am
Nonstop4h 05m
San Diego
Tue 9/1
12:20 pm-9:05 pm
1 stop6h 45m
$294
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 8/21
6:15 am-8:20 am
Nonstop4h 05m
San Diego
Mon 8/24
10:40 pm-7:35 am
1 stop6h 55m
$297
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 9/24
2:00 pm-8:37 pm
1 stop8h 37m
San Diego
Sun 9/27
10:25 pm-9:50 am
1 stop9h 25m
$307
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 8/15
2:20 pm-6:25 pm
1 stop6h 05m
San Diego
Sat 8/22
9:10 am-8:15 pm
1 stop9h 05m
$309
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 10/22
3:45 pm-8:05 pm
1 stop6h 20m
San Diego
Sun 10/25
10:40 pm-4:30 am
Nonstop3h 50m
$314
Quickest round-trip
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sun 10/25
6:30 am-8:55 am
Nonstop4h 25m
San Diego
Sun 11/1
6:35 am-12:35 pm
Nonstop4h 00m
$317
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 8/7
7:10 am-11:15 am
1 stop6h 05m
San Diego
Mon 8/10
10:40 pm-4:30 am
Nonstop3h 50m
$322
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 11/6
2:30 pm-6:55 pm
1 stop6h 25m
San Diego
Sun 11/15
10:40 pm-4:25 am
Nonstop3h 45m
$327
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Tue 8/4
8:25 pm-10:35 pm
Nonstop4h 10m
San Diego
Sat 8/8
10:40 pm-6:50 am
1 stop6h 10m
$341
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Mon 8/10
7:25 pm-11:35 pm
1 stop6h 10m
San Diego
Wed 8/26
12:32 pm-10:36 pm
1 stop8h 04m
$358
Showing 1-10 of 22 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 July.
| 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 79 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 July 18, 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 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 July 18, 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.
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 July 18, 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
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
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
National City
Chula Vista
Poway
La Mesa
Coronado
Santee
San Ysidro
Julian
Lemon Grove
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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 2,558,603 searches. Data last updated July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$344 | FlexibilityNo cancel fee | On-time63% |