$106+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
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 April, booked 62 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday
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 junio 12, 2025.
Round-trip from | $186 (Southwest) |
|---|---|
One-way from | $106 (Southwest) |
Popular in | January |
Cheapest in | December |
Average price | $377 |
Good round-trip deal | $297 or less |
Good one-way deal | $188 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 junio 12, 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 junio 12, 2025.
This Southwest deal was found by Cheapflights users on 6/9. 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.
This CheapOair deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/11. 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.
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 junio 12, 2025.
Use the filters below to find and compare flights from San Diego to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San DiegoChicago
SAN - MDW
SANMDW
San Diego
jue. 8/7
6:30 pm-12:30 am
Nonstop4h 00m
Chicago Midway
mar. 8/12
8:20 am-10:30 am
Nonstop4h 10m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
vie. 8/1
10:15 pm-8:44 am
1 stop8h 29m
Chicago Midway
vie. 8/8
7:21 pm-11:29 pm
1 stop6h 08m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
mié. 7/16
8:00 am-5:03 pm
1 stop7h 03m
Chicago Midway
mié. 7/23
6:02 pm-10:54 pm
1 stop6h 52m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
jue. 8/7
6:30 pm-12:30 am
Nonstop4h 00m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
jue. 6/26
7:31 pm-2:56 pm
1 stop17h 25m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
jue. 9/4
1:05 pm-10:01 pm
1 stop6h 56m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
lun. 9/1
6:20 am-5:37 pm
1 stop9h 17m
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.
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 June 9, 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 62 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 $160). Flying from San Diego to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 junio 12, 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 28% 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 June 8, 2025.
Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Tuesday 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.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 junio 12, 2025.
Read through reviews of airlines operating flights from San Diego to Chicago, such as Southwest, Delta and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Entertainment
Food
Boarding
Comfort
Crew
Reviews
Merlyn,Feb 2025
LAX - SMF
Overall
Entertainment
Food
Boarding
Comfort
Crew
Reviews
Merlyn,Feb 2025
LAX - SMF
Overall
Entertainment
Food
Boarding
Comfort
Crew
Reviews
Merlyn,Feb 2025
LAX - SMF
Overall
Entertainment
Food
Boarding
Comfort
Crew
Reviews
Merlyn,Feb 2025
LAX - SMF
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.
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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 3 airlines flying from San Diego to Midway
Discover the top 3 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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$223 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$258 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$306 | Average$457 | FlexibilityNo cancel fee | On-time63% |