$249 Cheap Flights from Madison (MSN) to Cleveland (CLE)

Madison (MSN) to Cleveland (CLE) at a glance

Explore a range of airlines providing flights from Madison (MSN) to Cleveland (CLE) on this domestic short-haul route. Evaluate your options between full-service and budget carriers to discover the itinerary that aligns with your budget and travel schedule while visiting Cleveland’s renowned attractions and neighborhoods. Get all the essential information for flights from Dane County Regional Airport (MSN) to Hopkins International Airport (CLE) to help you plan your next trip.

• Fastest flight duration: around 2h 30m in-flight, plus roughly 1 hour layover with one stop
• Route distance: roughly 400 miles (645 km)
• Flights per week: around 9 departures on average
• Typical fares (one-way): economy tickets often range from $115–$380, depending on seasonality and how far ahead you book

Flights from Dane County Regional Airport (MSN) to Hopkins International Airport (CLE)

Recent traveler bookings reveal the top airlines flying from Madison to Cleveland, particularly favored for their one-stop service. Popular layover airports include O'Hare International Airport (ORD) with an approximate 1-hour layover, Detroit Metropolitan Wayne County Airport (DTW) at around 1 hour and 15 minutes, and Minneapolis - St. Paul International Airport (MSP) with about a 1-hour layover. This variety allows you to compare prices, total travel times, and cabin classes to create the best travel itinerary for your needs.

• United: This full-service airline provides a convenient one-stop travel option, with one-way ticket prices generally falling between $115 and $410. United operates nearly 47% of flights on this route, featuring an in-flight duration of 2 hours and 30 minutes, and a total travel time of about 3 hours and 45 minutes, including the layover.
• American Airlines: Another full-service option, American Airlines offers one-stop service with one-way fares usually ranging from $115 to $355. This carrier accounts for around 33% of departures on this route, with a flight time of 2 hours and 30 minutes, resulting in a total journey time of roughly 3 hours and 45 minutes, layover included.
• Delta: As a full-service airline providing one-stop routes, Delta's one-way fares typically range from $115 to $370. Covering approximately 20% of departures for this journey, Delta's in-flight duration is 2 hours and 30 minutes, leading to a total travel time of about 3 hours and 45 minutes when factoring in the layover.

Best time to fly from Madison (MSN) to Cleveland (CLE)

The most popular months for travelers flying from Madison to Cleveland are March, April, and July, when peak temperatures in Cleveland reach up to 73°F in July. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 43.2°F. For better deals, August usually offers the lowest average one-way fare around $187. Flight availability peaks in July, August, and October, with approximately 11 flights per week, making it easier to find convenient departure times. January and June have the fewest flights, with approximately 8 flights per week.

• Cheapest time to fly: August usually offers good deals with average one-way fare around $187, roughly 16% cheaper than the yearly average.
• Another budget-friendly time to fly: July typically offers an average one-way fare of around $204.
• Most flight options: July, August, and October have the highest number of flights from Madison to Cleveland, with approximately 11 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Madison (MSN) to Cleveland (CLE)

• Madison to Cleveland (MSN-BKL): Burke Lakefront Airport (BKL) is located approximately 11 miles from Hopkins International Airport (CLE).

How to find the best prices for flights from Madison (MSN) to Cleveland (CLE)

Getting some of the best deals on flights from Madison to Cleveland is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, coinciding with when most travelers make their reservations. Morning departures from 5 am to 12 pm tend to offer lower prices and are also the most popular times to fly. Additionally, flying on Saturday often results in cheaper fares, although Friday remains the busiest travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Hopkins International Airport from Dane County Regional Airport

Cleveland welcomes travelers from Madison with a range of transport options based on price, convenience, and proximity. Here's how to reach Cleveland efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Cleveland, with private rides that can be arranged in advance.
• Car rental: Renting a car from Hopkins International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hopkins International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From Hopkins International Airport, Cleveland Hopkins Airport Station (a metro station) is just a short 0.1 miles away on foot, while Cleveland Seaport (a seaport) is located about 0.2 miles away on foot, providing convenient access to both train and sea travel.

Madison to Cleveland Flights

The cheapest times to fly from Madison to Cleveland

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

The best time to book a flight from Madison to Cleveland

Sunday is one of the best days to book for cheap flights from Madison to Cleveland: 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 Madison to Cleveland

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 Madison to Cleveland in 2026. You can also book with separate airlines for your outbound and return journeys, from $249 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 Madison to Cleveland 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 Madison to Cleveland 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.