Cheap flights from Madison

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Madison Flight Information
Origin airport IATA code
ESN

Sourcing the best flights from Madison on ebookers

If you’re seeking a flight from Madison, you can swiftly and easily find exactly what you’re looking for using ebookers. Our easy-to-use tool will let you select the destination and ideal travel dates to immediately see which routes and airlines are available. Have a preferred airline in mind for the trip? You can filter your ebookers search to see if they have flights from ESN. For more bespoke options, you can also set your search for multiple destinations and flights that are refundable, so you can have the most relevant information in moments.

Getting the best deal on a cheap flight from ESN

There are a few golden rules for keeping costs low when booking flights from Madison. The first thing to think about is being flexible on your travel dates. It can help to shift your departure by a day, or even a few hours, as prices can vary by significant amounts. Use ebookers to compare and contrast your options ahead of time, and you can make a savvy decision. Want more savings? If book the hotel at your chosen destination through ebookers while also arranging your flight from Madison, you can get a discount of up to 15% off the total price. For help on which pad to pick, you can make use of our snappy hotel descriptions, which are accompanied by useful photos.

Getting things going at your destination

With ebookers, you don’t just have access to the latest, constantly updated information on flights from ESN. You can also get inspiration on the most interesting things to get up to when you’re there. Just check out our Things to Do tool and you’ll soon be drawing up an exciting itinerary. And if you’re keen to take in as much of the wider area as possible, you could also look into the best car hire deals and have your very own set of wheels waiting, so you can roam to your heart’s content.

Featured Hotels near Madison

The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
The price is €184 per night from 16 Feb to 17 Feb
€184
16 Feb - 17 Feb
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at The Wildset. During your stay, you're just a quick walk from Higgins Yacht Yard and Marina. Enjoy features like free WiFi in public areas and free self-parking, plus a restaurant. This property offers pet-friendly amenities, such as food and water bowls.
9.6/10 Exceptional! (417 reviews)
Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown.

Reviewed on 21 Jan 2026

Opens in a new windowThe Wildset
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
The price is €166 per night from 15 Mar to 16 Mar
€166
15 Mar - 16 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at The Tidewater Inn. During your stay, you're just a quick walk from Avalon Theatre. Free WiFi in public areas, free self-parking and a full-service spa are available.
8.8/10 Excellent! (848 reviews)
Beautiful historic but with nice mix-in of modern hotel. Friendly, professional staff. Great location. My wife and I had a fantastic stay.

Reviewed on 13 Jan 2026

Opens in a new windowThe Tidewater Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
The price is €202 per night from 15 Mar to 16 Mar
€202
15 Mar - 16 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the pool at Hyatt Regency Chesapeake Bay. During your stay, you'll be within walking distance of Bay Country Shop. Enjoy features like free WiFi in public areas and free self-parking, plus 2 outdoor pools. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (1,003 reviews)
Nice stay, but a little too crowded.

Reviewed on 30 Jan 2026

Opens in a new windowHyatt Regency Chesapeake Bay
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Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
The price is €112 per night from 22 Feb to 23 Feb
€112
22 Feb - 23 Feb
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Rod 'N' Reel Resort. During your stay, you're just a quick walk from Chesapeake Bay. Features include 2 restaurants, 2 bars and an indoor pool.
8.4/10 Very Good! (1,002 reviews)
Nice staff

Reviewed on 7 Feb 2026

Opens in a new windowRod 'N' Reel Resort
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099 Solomons MD
During your stay at Solomons Inn Resort & Marina, you're just a quick walk from Southern Branch Library. You'll find features such as free breakfast, free WiFi in public areas and free self-parking.
8/10 Very Good! (991 reviews)
Everything was great just need better outlets and b8gger fridge

Reviewed on 19 Jan 2026

Opens in a new windowSolomons Inn Resort & Marina
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Our customers tell us that they can't get enough of the helpful staff at St Michaels Inn. During your stay, you'll be within walking distance of St. Michaels Winery. You'll find features such as free breakfast, free WiFi in public areas and free self-parking.
8/10 Very Good! (1,000 reviews)
Very good motel

Reviewed on 25 Jan 2026

Opens in a new windowSt Michaels Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.