Cheap Flights from Sanford (SFM) to Chicago (MDW)

Popular airlines from Sanford, ME (SFM-Sanford Seacoast Regional) to Chicago Midway Airport (MDW)

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Flights from Sanford (SFM) to Chicago (MDW)
Origin airport
Sanford Seacoast Regional
Destination airport
Midway Intl.
Distance
871 mi

Sanford to Chicago Flights

The cheapest times to fly from Sanford 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 Sanford to Chicago are during the month of . You can find some of the cheapest flights from Sanford to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Sanford to Chicago

Sunday is one of the best days to book for cheap flights from Sanford 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 Sanford 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 Sanford 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 Sanford 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 Sanford 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 Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from SFM 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 SFM to MDW?
The cheapest flights from SFM 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.
What is the cheapest airline that flies from SFM to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from SFM to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights available from Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from SFM to MDW?
Typically you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can change based on the season, airline 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 Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW) route, fly before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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 Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book your flight from SFM to MDW often results in higher prices. Although you may find some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of landing a bargain.
Is it cheaper to book a SFM to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SFM to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one place will take the stress out of travel planning. Just pick your flights and select from our extensive range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Sanford, ME (SFM-Sanford Seacoast Regional) to Midway Intl. Airport (MDW)?
If you reserved your SFM to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

Explore a world of travel with Expedia

*Available to One Key members.