$79+ Cheap flights from San Diego (SAN) to Midway (MDW)
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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Feb 26 — Mar 51
1 adult, Economy
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Find cheap flights from San Diego to Midway 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 San Diego to Chicago Midway are usually found in December or November, booked 65 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap flight deals from San Diego to Midway
Cheapest flights from San Diego to MidwayExplore the most affordable flight options available from San Diego to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
Explore the most affordable flight options available from San Diego to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
This Southwest deal was found by Cheapflights users on 1/24. 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 2/287:15 am
SAN
- MDW
Nonstop4h 00m
Southwest
Wed 3/47:50 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Deal found 1/24![Southwest logo]()
$161
This Southwest deal was found by Cheapflights users on 1/24. 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 2/236:30 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 2/288:40 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Deal found 1/24![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 1/27. 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 2/252:00 pm
SAN
- MDW
1 stop5h 15m
Southwest
Sat 2/288:40 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Deal found 1/27![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:25 am
SAN
- MDW
1 stop15h 16m
Frontier
Sat 2/286:25 am
MDW
- SAN
2 stops19h 43m
Frontier
Deal found 1/25![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:25 am
SAN
- MDW
2 stops12h 47m
Frontier
Mon 3/27:25 pm
MDW
- SAN
1 stop26h 59m
Frontier
Deal found 1/27![Frontier logo]()
$171
This Southwest deal was found by Cheapflights users on 1/25. 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 2/193:30 pm
SAN
- MDW
1 stop6h 15m
Southwest
Sat 2/288:40 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Deal found 1/25![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 1/27. 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 2/246:25 am
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 3/32:10 pm
MDW
- SAN
1 stop7h 30m
Southwest
Deal found 1/27![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 1/25. 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 4/1810:40 pm
SAN
- MDW
1 stop6h 10m
Southwest
Tue 4/215:15 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Deal found 1/25![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 1/25. 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 3/146:45 am
SAN
- MDW
Nonstop4h 00m
Southwest
Mon 3/168:55 pm
MDW
- SAN
Nonstop4h 30m
Southwest
Deal found 1/25![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:36 pm
SAN
- MDW
1 stop21h 54m
Frontier
Thu 3/55:16 pm
MDW
- SAN
2 stops32h 52m
Frontier
Deal found 1/27![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:25 am
SAN
- MDW
2 stops14h 12m
Frontier
Sun 2/223:21 pm
MDW
- SAN
1 stop30h 14m
Frontier
Deal found 1/26![Frontier logo]()
$183
Find flight deals from San Diego to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Midway (MDW). 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 27, 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 | June |
Cheapest in | December |
Average price | $323 |
Good round-trip deal | $267 or less |
Good one-way deal | $205 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Midway 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 27, 2026.
Use the filters below to find and compare flights from San Diego to Chicago Midway Airport that are best for you.
Fly from
San Diego
Fly to
Midway
Route
Depart
Return
Price
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 2/28
7:15 am-1:15 pm
Nonstop4h 00m
Chicago Midway
Wed 3/4
2:45 pm-6:35 pm
1 stop5h 50m
$170
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Mon 2/23
6:30 pm-12:25 am
Nonstop3h 55m
Chicago Midway
Fri 2/27
3:10 pm-5:40 pm
Nonstop4h 30m
$187
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sun 3/8
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Fri 3/13
8:55 pm-11:25 pm
Nonstop4h 30m
$187
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 4/24
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Mon 4/27
8:45 pm-11:10 pm
Nonstop4h 25m
$187
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 5/14
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Sat 5/16
6:10 pm-8:30 pm
Nonstop4h 20m
$189
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 4/24
6:40 am-12:35 pm
Nonstop3h 55m
Chicago Midway
Sun 4/26
9:10 pm-11:25 pm
Nonstop4h 15m
$197
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 2/28
5:55 pm-11:45 pm
Nonstop3h 50m
Chicago Midway
Sat 3/7
8:55 pm-11:25 pm
Nonstop4h 30m
$197
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 3/4
10:05 am-4:05 pm
Nonstop4h 00m
Chicago Midway
Tue 3/10
5:45 am-8:10 am
Nonstop4h 25m
$197
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 4/15
11:30 am-8:40 pm
1 stop7h 10m
Chicago Midway
Wed 4/22
6:45 am-9:00 am
Nonstop4h 15m
$197
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 4/9
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Mon 4/13
8:45 pm-11:10 pm
Nonstop4h 25m
$197
Showing 1-10 of 21 results
Compare providers for flights from San Diego to Midway
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 San Diego to Midway in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on San Diego-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Diego-Chicago Midway Airport 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 San Diego-Chicago Midway Airport 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 San Diego to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Diego 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 San Diego to Chicago Midway Airport
How far ahead should I book a flight from San Diego to Chicago Midway Airport?
Use this chart to determine the optimal time to book a round-trip flight from San Diego to Midway. Price data was last updated on January 23, 2026.
The price you pay for your flight from San Diego to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 65 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from San Diego to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $110). Flying from San Diego to Chicago Midway Airport in August is currently the most expensive (average of $228). 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 SAN to MDW?
Find hourly flight availability from San Diego to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 27, 2026.
It’s optimal to fly from San Diego to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight in the evening.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated January 27, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from San Diego to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Diego to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for San Diego to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from San Diego to Midway
Discover the top 2 airlines that operate flights from San Diego to Midway. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$110 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$378 | FlexibilityNo cancel fee | On-time63% |