Cheap Flights from San Diego (SDM) to Chicago (MDW)

Popular airlines from San Diego, CA (SDM-Brown Field Municipal) to Chicago Midway Airport (MDW)

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Flights from San Diego (SDM) to Chicago (MDW)
Origin airport
Brown Field Municipal
Destination airport
Midway Intl.
Distance
1720 mi

San Diego to Chicago Flights

The cheapest times to fly from San Diego to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Diego to Chicago are during the month of . You can find some of the cheapest flights from San Diego to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Diego to Chicago

Sunday is one of the best days to book for cheap flights from San Diego to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Diego to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Diego to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Diego to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Diego to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from SDM to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from SDM to MDW?
The cheapest flights from SDM to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW)?
Although San Diego, CA (SDM-Brown Field Municipal) has no direct flights to Midway Intl. Airport (MDW), other airports have nonstop routes. Jetting off from San Diego Intl. Airport (SAN) will get you to Chicago without any detours.
What is the cheapest airline that flies from SDM to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from SDM to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW)?
There are no daily direct flights departing from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from SDM to MDW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* However, this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW)?
To avoid potential delays on the San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from SDM to MDW are generally more expensive. To lock in the best prices, start searching for flights well ahead of time. That being said, if you're flexible with your travel plans, you may land a cheap ticket just before your departure.
Is it cheaper to book a SDM to MDW flight and hotel package?
You can save money by securing a SDM to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After selecting your preferred accommodations and flights, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from San Diego, CA (SDM-Brown Field Municipal) to Midway Intl. Airport (MDW)?
Generally, it's possible to reschedule or cancel your SDM to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

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