Cheap Flights from Chicago (MDW) to Leesburg (LEE)

Popular airlines from Chicago Midway Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.) cost?
Secure a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)?
Flying in is a great way to save, as it's the cheapest month for flights between MDW and LEE. You'll usually find the lowest prices during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to LEE flight.
How many flights per day from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)?
There aren't any daily direct flights from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way in no time.
What day of the week has the most flights from MDW to LEE?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary depending on various factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)?
Select a flight from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time are on average 22% more likely to be 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.
What airports do you fly into for Leesburg from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO). This is the only airport in Leesburg you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.) last-minute?
Last-minute bookings from MDW to LEE are typically more expensive. To secure the lowest rates, start looking for flights early. That said, if you can play around with your travel dates, it's possible to find a cheap ticket right before your trip.
Is it cheaper to book a MDW to LEE flight and hotel package?
Opting for a MDW to LEE flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Select from our impressive range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Leesburg, FL (LEE-Leesburg Intl.)?
Generally, it's possible to reschedule or cancel your MDW to LEE flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to 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.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Leesburg Intl.
Distance
955 mi

Book with confidence

Book with confidence

Chicago to Leesburg Flights

The cheapest times to fly from Chicago to Leesburg

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

 

The best time to book a flight from Chicago to Leesburg

Sunday is one of the best days to book for cheap flights from Chicago to Leesburg: 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 Chicago to Leesburg

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 Chicago to Leesburg 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 Chicago to Leesburg 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 Chicago to Leesburg 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.

 

Chicago to Leesburg Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.