$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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAN
Mar 20 — Mar 271
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 February or January, booked 80 days in advance, depart on a Saturday or Thursday 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 February 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 February 18, 2026.
This Southwest deal was found by Cheapflights users on 2/16. 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.
Wed 3/115:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Wed 3/1810:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/16![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Sat 3/79:16 pm
MDW
- SAN
1 stop28h 00m
Frontier
Tue 3/106:25 am
SAN
- MDW
2 stops26h 00m
Frontier
Deal found 2/16![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 2/15. 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 4/116:10 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Sat 4/1810:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/15![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:15 am
MDW
- SAN
1 stop10h 10m
Frontier
Mon 5/46:55 am
SAN
- MDW
1 stop13h 26m
Frontier
Deal found 2/17![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Wed 3/1111:25 am
MDW
- SAN
2 stops14h 43m
Frontier
Fri 3/132:57 pm
SAN
- MDW
1 stop29h 48m
Frontier
Deal found 2/15![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:25 am
MDW
- SAN
2 stops14h 43m
Frontier
Wed 3/183:16 pm
SAN
- MDW
1 stop29h 29m
Frontier
Deal found 2/17![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 2/17. 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.
Tue 3/175:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Mon 3/2310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 2/15. 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 3/78:55 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Tue 3/1010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/15![Southwest logo]()
$192
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 February 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 February 18, 2026.
This Southwest deal was found by Cheapflights users on 2/15. 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 4/116:15 am
MDW
- SAN
Nonstop4h 15m
Southwest
Sat 4/186:20 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 2/15![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 2/15. 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 5/26:10 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Tue 5/57:50 am
SAN
- MDW
1 stop6h 45m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/15. 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.
Thu 4/96:35 am
MDW
- SAN
Nonstop4h 15m
Southwest
Mon 4/1310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/17. 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.
Fri 4/248:45 pm
MDW
- SAN
Nonstop4h 25m
Southwest
Mon 4/2710:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/15. 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.
Wed 3/115:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Fri 3/134:45 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/15. 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 5/18:45 pm
MDW
- SAN
Nonstop4h 25m
Southwest
Sat 5/96:20 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/16. 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 3/136:05 am
MDW
- SAN
Nonstop4h 30m
Southwest
Tue 3/2410:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/16![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 2/15. 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 5/26:10 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Sun 5/310:40 pm
SAN
- MDW
1 stop6h 15m
Southwest
Deal found 2/15![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 2/14. 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 3/1711:15 am
MDW
- SAN
1 stop7h 30m
Southwest
Tue 3/2410:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/14![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 2/15. 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.
Thu 4/95:10 am
MDW
- SAN
1 stop6h 30m
Southwest
Fri 4/1010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/15![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 2/14. 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 4/38:55 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Wed 4/87:50 am
SAN
- MDW
1 stop6h 45m
Southwest
Deal found 2/14![Southwest logo]()
$207
Last-minute flights from Midway to San DiegoDiscover last-minute flight deals from Midway to San Diego. Data last updated February 18, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Diego. Data last updated February 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Sat 3/79:16 pm
MDW
- SAN
1 stop28h 00m
Frontier
Tue 3/106:25 am
SAN
- MDW
2 stops26h 00m
Frontier
Deal found 2/16![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 2/15. 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 3/78:55 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Tue 3/1010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/15![Southwest logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Sat 3/79:16 pm
MDW
- SAN
1 stop28h 00m
Frontier
Mon 3/169:08 pm
SAN
- MDW
2 stops35h 17m
Frontier
Deal found 2/14![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/92:16 pm
MDW
- SAN
1 stop26h 15m
Frontier
Fri 4/1011:58 am
SAN
- MDW
2 stops9h 15m
Frontier
Deal found 2/16![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 2/16. 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.
Wed 3/115:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Wed 3/1810:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/16![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 2/15. 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.
Wed 3/115:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Fri 3/134:45 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Wed 3/1111:25 am
MDW
- SAN
2 stops14h 43m
Frontier
Fri 3/132:57 pm
SAN
- MDW
1 stop29h 48m
Frontier
Deal found 2/15![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:25 am
MDW
- SAN
2 stops14h 43m
Frontier
Wed 3/183:16 pm
SAN
- MDW
1 stop29h 29m
Frontier
Deal found 2/17![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 2/16. 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 3/136:05 am
MDW
- SAN
Nonstop4h 30m
Southwest
Fri 3/2010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/16![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 2/17. 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.
Tue 3/175:55 am
MDW
- SAN
1 stop6h 35m
Southwest
Tue 3/2410:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$187
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 February 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 February 18, 2026.
This Southwest deal was found by Cheapflights users on 2/16. 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 4/186:15 am
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 2/16![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Wed 3/1111:25 am
MDW
- SAN
2 stops14h 43m
Frontier
Deal found 2/14![Frontier logo]()
$80
This Trip.com deal was found by Cheapflights users on 2/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:15 am
MDW
- SAN
1 stop10h 10m
Frontier
Deal found 2/18![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Thu 4/236:15 am
MDW
- SAN
1 stop10h 10m
Frontier
Deal found 2/15![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 5/46:15 am
MDW
- SAN
2 stops39h 49m
Frontier
Deal found 2/16![Frontier logo]()
$86
This Trip.com deal was found by Cheapflights users on 2/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:15 am
MDW
- SAN
1 stop10h 10m
Frontier
Deal found 2/16![Frontier logo]()
$87
This Southwest deal was found by Cheapflights users on 2/17. 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.
Wed 3/255:45 am
MDW
- SAN
Nonstop4h 25m
Southwest
Deal found 2/17![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 5/116:15 am
MDW
- SAN
2 stops33h 37m
Frontier
Deal found 2/18![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 2/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:11 pm
MDW
- SAN
1 stop8h 43m
Frontier
Deal found 2/17![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:15 pm
MDW
- SAN
1 stop9h 56m
Frontier
Deal found 2/18![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 2/16. 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 4/256:15 am
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 2/16![Southwest logo]()
$96
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 February 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $167 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | December |
Cheapest in | February |
Average price | $207 |
Good round-trip deal | $252 or less |
Good one-way deal | $78 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 February 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
Midway
Fly to
San Diego
Route
Depart
Return
Price
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 4/11
6:15 am-8:30 am
Nonstop4h 15m
San Diego
Sat 4/18
6:20 am-12:20 pm
Nonstop4h 00m
$174
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 5/2
6:10 pm-8:30 pm
Nonstop4h 20m
San Diego
Tue 5/5
7:50 am-4:35 pm
1 stop6h 45m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 4/9
6:35 am-8:50 am
Nonstop4h 15m
San Diego
Mon 4/13
10:40 pm-4:35 am
Nonstop3h 55m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 4/24
8:45 pm-11:10 pm
Nonstop4h 25m
San Diego
Mon 4/27
10:40 pm-4:35 am
Nonstop3h 55m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Wed 3/11
5:45 am-8:10 am
Nonstop4h 25m
San Diego
Fri 3/13
4:45 pm-10:35 pm
Nonstop3h 50m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 5/1
8:45 pm-11:10 pm
Nonstop4h 25m
San Diego
Sat 5/9
6:20 am-12:20 pm
Nonstop4h 00m
$177
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 3/13
6:05 am-8:35 am
Nonstop4h 30m
San Diego
Tue 3/24
10:40 pm-4:35 am
Nonstop3h 55m
$187
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 5/2
6:10 pm-8:30 pm
Nonstop4h 20m
San Diego
Sun 5/3
10:40 pm-6:55 am
1 stop6h 15m
$197
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Tue 3/17
11:15 am-4:45 pm
1 stop7h 30m
San Diego
Tue 3/24
10:40 pm-4:35 am
Nonstop3h 55m
$197
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Thu 4/9
5:10 am-9:40 am
1 stop6h 30m
San Diego
Fri 4/10
10:40 pm-4:35 am
Nonstop3h 55m
$207
Showing 1-10 of 21 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 February.
| 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 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?
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 February 13, 2026.
To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to San Diego, you should look to book at least 80 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago Midway Airport to San Diego?
Currently, 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 $295). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SAN?
Find hourly flight availability from Midway to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 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 afternoon, which can drop the price by up to 37% 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 February 17, 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 mornings 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 February 18, 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.
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
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
Chula Vista
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove
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
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
San Diego flight routes
Alternative routes for Midway to San Diego
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Diego by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to San Diego by cabin class
Find flights from Midway to San Diego, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Diego flights
Browse other Midway and San Diego flight options. Last updated on February 18, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on February 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San Diego
Explore flights to San Diego departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 18, 2026.
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 February 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$173 | Average$308 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$353 | FlexibilityNo cancel fee | On-time63% |