$279 Cheap Flights from Chicago (MDW) to Lebanon (LEB)

View $279 flight on Sat, Oct 11, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Lebanon, NH (LEB-Lebanon Municipal)

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Cheap Flights from Chicago to Lebanon (MDW-LEB)

Prices were available within the past 7 days and start at $279 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB) cost?
Snag a cheap one-way flight from $279 or cheap return flight from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB) 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 Lebanon Municipal Airport (LEB)?
Planning your trip for is a great way to save, as it's the cheapest month for flights between MDW and LEB. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from MDW to LEB. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB)?
Nonstop flights from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to LEB?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary depending on a range of factors, such as 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 Lebanon Municipal Airport (LEB)?
Select a flight from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB) last-minute?
Holding off until just before your departure to book a flight from MDW to LEB generally means paying more. While you may come across some last-minute offers, there's no guarantee. Be flexible with your travel plans to boost your chances of landing a bargain.
Is it cheaper to book a MDW to LEB flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to LEB flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place will take the stress out of travel planning. Just pick your flights and select from our extensive range of stays, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Lebanon Municipal Airport (LEB)?
If you reserved your MDW to LEB flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Lebanon Municipal
Distance
792 mi

Book with confidence

Book with confidence

Chicago to Lebanon Flights

The cheapest times to fly from Chicago to Lebanon

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

 

The best time to book a flight from Chicago to Lebanon

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

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 Lebanon in 2025. You can also book with separate airlines for your outbound and return journeys, from $279 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 Lebanon 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 Lebanon 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 Lebanon Flights

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Explore a world of travel with Expedia

*Available to One Key members.