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

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

Explore a range of airlines providing flights from Cleveland (CLE) to Madison (MSN) on this convenient domestic route. Compare various options from full-service carriers to uncover the cheapest flights from Cleveland that suit your budget and schedule. As you plan your trip, discover Madison's popular attractions and neighborhoods while ensuring you have all the essential details for your flight from Hopkins International Airport to Dane County Regional Airport.

• Fastest flight duration: around 2h 45m in-flight, plus roughly 1h 15m 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 $110–$380, depending on seasonality and how far ahead you book

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

Based on recent travel bookings, here are the top airlines favored by travelers flying from Cleveland to Madison, typically utilizing one-stop services. Common layover points include O'Hare International Airport (ORD) with an average layover of about 1 hour and 15 minutes, Detroit Metropolitan Wayne County Airport (DTW) at roughly 1 hour, and Minneapolis - St. Paul International Airport (MSP) with a layover of around 55 minutes. These options allow you to tailor your journey by balancing price, total travel time, and cabin class for the ideal travel experience.

• United: This full-service airline provides one-stop flights, with one-way ticket prices generally falling between $115 and $355. It represents around 44% of departures on this route, featuring an in-flight duration of 2 hours and 45 minutes, and a total travel time of about 4 hours, including layover.
• American Airlines: Known for its comprehensive service, this carrier offers one-stop options with one-way fares typically ranging from $110 to $360. It makes up approximately 31% of the departures for this route, with an in-air time of 2 hours and 45 minutes and an overall journey time of roughly 4 hours, layover included.
• Delta: As another full-service option, Delta features one-stop flights priced from $110 to $420 for one-way travel. It accounts for around 25% of departures on this route, with an in-flight time of 2 hours and 45 minutes, and an estimated total travel duration of about 4 hours, factoring in layover.

Travelers flying from Cleveland to Madison can enhance their journey by upgrading their flight. Delta provides options for both first class and premium economy, while United offers first-class seating.

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

The most popular months for travelers flying from Cleveland to Madison are March, April, and October, when peak temperatures in Madison reach up to 50°F in October. If you prefer quieter travel, consider February, the least busy time to visit with temperatures around 20.7°F and typically the lowest average one-way fare (around $191). Flight availability peaks in September, with approximately 12 flights per week, making it easier to find convenient departure times. January and December have the fewest flights, with approximately 8 flights per week.

• Cheapest time to fly: February usually offers good deals with average one-way fare around $191, roughly 12% cheaper than the yearly average.
• More budget-friendly months to fly: September and August typically offer average one-way fares of around $205.
• Most flight options: September has the highest number of flights from Cleveland to Madison, with approximately 12 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 Cleveland (CLE) to Madison (MSN)

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

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

Getting some of the best deals on flights from Cleveland to Madison 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 available when booking 2 to 8 weeks in advance, which coincides with when most travelers make their reservations. Departures in the morning (5 AM to 12 PM) are often less expensive and are also the most popular flight times. Additionally, flying on Wednesday typically offers lower prices, even though Friday is the most favored 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 Dane County Regional Airport from Hopkins International Airport

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

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Madison, with private rides that can be arranged in advance.
• Car rental: Renting a car from Dane County Regional Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Dane County Regional 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 Dane County Regional Airport, Madison Station (a train station) is located about 7.2 miles away by car, while Madison Dutch Mill Park and Ride (a bus station) is approximately 9.2 miles from the airport, also conveniently reached by car.

Cleveland to Madison Flights

The cheapest times to fly from Cleveland to Madison

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

The best time to book a flight from Cleveland to Madison

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

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 Cleveland to Madison 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 Cleveland to Madison 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 Cleveland to Madison 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.