$86+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Nov 29 — Dec 61
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 September or December, booked 65 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap 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 October 30, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $163 (Southwest) |
One-way from | $86 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $308 |
Good round-trip deal | $277 or less |
Good one-way deal | $203 or less |
Find 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 October 30, 2025.
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 October 30, 2025.
This Southwest deal was found by Cheapflights users on 10/28. 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.
Wed 11/195:00 pmSAN - MDW
Nonstop3h 55mSouthwest
Wed 11/265:15 amMDW - SAN
1 stop6h 10mSouthwest
Deal found 10/28![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 12/144:47 pmSAN - MDW
1 stop16h 21mFrontier
Sun 12/2110:50 pmMDW - SAN
1 stop27h 09mFrontier
Deal found 10/30![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/26:25 amSAN - MDW
2 stops24h 21mFrontier
Fri 12/512:18 pmMDW - SAN
1 stop13h 41mFrontier
Deal found 10/29![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:47 pmSAN - MDW
1 stop16h 21mFrontier
Sun 12/77:24 pmMDW - SAN
1 stop20h 46mFrontier
Deal found 10/28![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 12/88:05 pmSAN - MDW
1 stop7h 00mSouthwest
Wed 12/108:20 amMDW - SAN
Nonstop4h 30mSouthwest
Deal found 10/30![Southwest logo]()
$175
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:14 amSAN - MDW
1 stop6h 08mFrontier
Thu 11/206:15 pmMDW - SAN
1 stop7h 29mFrontier
Deal found 10/28![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/48:10 pmSAN - MDW
2 stops24h 02mFrontier
Sun 12/712:18 pmMDW - SAN
1 stop8h 57mFrontier
Deal found 10/29![Frontier logo]()
$179
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:14 amSAN - MDW
1 stop6h 08mFrontier
Fri 11/1412:30 pmMDW - SAN
1 stop22h 57mFrontier
Deal found 10/29![Frontier logo]()
$182
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:25 amSAN - MDW
1 stop8h 36mFrontier
Thu 11/206:15 pmMDW - SAN
1 stop7h 29mFrontier
Deal found 10/30![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:14 amSAN - MDW
1 stop6h 08mFrontier
Mon 11/108:30 amMDW - SAN
1 stop10h 10mFrontier
Deal found 10/28![Frontier logo]()
$186
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 October 30, 2025.
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
Tue 1/6
6:25 am-12:25 pm
Nonstop4h 00m
Chicago Midway
Tue 1/13
7:50 pm-10:20 pm
Nonstop4h 30m
$217
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 11/26
7:00 pm-12:55 am
Nonstop3h 55m
Chicago Midway
Tue 12/2
8:35 pm-11:00 pm
Nonstop4h 25m
$217
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 12/4
6:30 am-12:35 pm
Nonstop4h 05m
Chicago Midway
Sun 12/7
3:00 pm-5:25 pm
Nonstop4h 25m
$227
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 12/4
6:30 am-12:35 pm
Nonstop4h 05m
Chicago Midway
Fri 12/5
5:15 pm-9:10 pm
1 stop5h 55m
$232
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sun 12/7
6:35 am-12:40 pm
Nonstop4h 05m
Chicago Midway
Tue 12/9
5:15 pm-9:10 pm
1 stop5h 55m
$232
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 1/10
6:15 am-4:16 pm
1 stop8h 01m
Chicago Midway
Tue 1/13
1:49 pm-8:53 pm
1 stop9h 04m
$237
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 12/6
6:15 am-3:44 pm
1 stop7h 29m
Chicago Midway
Sat 12/13
4:29 pm-11:35 pm
1 stop9h 06m
$237
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 12/6
6:15 am-3:44 pm
1 stop7h 29m
Chicago Midway
Tue 12/9
1:14 pm-6:21 pm
1 stop7h 07m
$237
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Mon 12/8
7:20 am-6:00 pm
1 stop8h 40m
Chicago Midway
Fri 12/12
1:14 pm-6:21 pm
1 stop7h 07m
$237
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 11/21
7:35 pm-1:30 am
Nonstop3h 55m
Chicago Midway
Mon 11/24
6:45 am-11:50 am
1 stop7h 05m
$237
Showing 1-10 of 18 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on San Diego-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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 October 24, 2025.
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 October 30, 2025.
It’s optimal to fly from San Diego to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the evening.
What is the cheapest day to fly from San Diego to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from San Diego to Midway. Price data was last updated on October 26, 2025.
Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 October 30, 2025.
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.
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Overall
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
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 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 locationsMerrillville
Lansing
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 October 30, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$123 | Average$219 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$414 | FlexibilityNo cancel fee | On-time63% |