$99 Cheap Flights to Madison
One-way
Departing from
United States
Going to
Madison, United States
Madison (MSN)
United States • May, 2026
90% AI deal score
$423 $99
Madison (MSN)
United States • May, 2026
90% AI deal score
$423 $99
Madison (MSN)
United States • May, 2026
90% AI deal score
$423 $100
Madison (MSN)
United States • May, 2026
89% AI deal score
$423 $109
Top Cheap Flight Deals from United States to Madison
Recent round-trip flight deals to Madison
Fri, Feb 20 - Mon, Mar 2
Cheapest
Fort Myers (RSW) - Madison (MSN)
Sun Country Airlines airlines • Direct
Madison (MSN) - Fort Myers (RSW)
Sun Country Airlines airlines • Direct
$273
$258
-$15
5%
Wed, May 13 - Fri, Jun 12
Pensacola (PNS) - Madison (MSN)
Spirit Airlines airlines • 1 stop • Orlando (MCO)
Madison (MSN) - Pensacola (PNS)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$238
$265
+$27
11%
Wed, Aug 19 - Fri, Aug 28
Pensacola (PNS) - Madison (MSN)
Spirit Airlines airlines • 1 stop • Orlando (MCO)
Madison (MSN) - Pensacola (PNS)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$250
$268
+$18
7%
Tue, Jun 23 - Sat, Jun 27
Champaign (CMI) - Madison (MSN)
United Airlines airlines • 1 stop • Chicago (ORD)
Madison (MSN) - Champaign (CMI)
United Airlines airlines • 1 stop • Chicago (ORD)
$565
$288
-$277
49%
Tue, Mar 24 - Sat, Apr 11
Pensacola (PNS) - Madison (MSN)
Spirit Airlines airlines • 1 stop • Orlando (MCO)
Madison (MSN) - Pensacola (PNS)
Breeze Airways airlines • 1 stop • Orlando (MCO)
$238
$304
+$66
28%
Tue, Mar 24 - Sat, Apr 4
Pensacola (PNS) - Madison (MSN)
Spirit Airlines airlines • 1 stop • Orlando (MCO)
Madison (MSN) - Pensacola (PNS)
Breeze Airways airlines • 1 stop • Orlando (MCO)
$238
$308
+$70
29%
The cheapest time to fly to Madison
Ready to jet to Madison on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Last-Minute Flights from United States to Madison
Need to get to Madison ASAP? Even if you're booking a flight on short notice, there are often last-minute deals available:
Next 2 weeks deals
Last Minute Flight Deals!
Great deals on flights to Madison departing in the next two weeks, with prices starting from $304.
⌛ Last-Minute
Gunnison - MSN
A great last-minute steal for a cross-country flight.
Found 1 week ago
$304
one-way
Facts About Flights from United States to Madison
To help you plan your journey, here are some quick Madison flight facts and tips.
Madison city airports
Dane County Regional Airport (MSN) is the primary airport serving Madison, Wisconsin. It offers a convenient and accessible gateway to the region, with a variety of airlines providing both domestic and international connections. Passengers can expect a range of amenities, including parking options, restaurants, and shops, ensuring a comfortable travel experience. The airport's location provides easy access to downtown Madison and surrounding areas, making it a popular choice for travelers visiting the city.
Pro tip: search “Madison (Any)” to see fares to all Madison airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Madison
Cheapest airport
Chicago Rockford International Airport (RFD)
Don't sleep on Chicago Rockford International Airport! (RFD) It's a smaller airport, but it can offer some seriously sweet deals and is approximately an hour and half away from Madison. It's known for being a cargo hub, but passenger flights are available as well!
Nonstop vs. 1-stop
20+ cities
While Madison isn't a major aviation hub, it serves as a convenient secondary airport, offering several popular routes connecting you to destinations like Chicago, Minneapolis, and Detroit.
Number of airlines
10+ airlines
More than 10 airlines operate flights in and out of Madison, with popular choices being American, Delta, United, Frontier, and Southwest.
Typical price range (round-trip)
$120 - $600
MSN Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
MSN airport insights
Best days to catch a deal
Tue, Sun
Based on the data, Tuesday has the most deals for flights departing from Dane County Regional Airport. Therefore, you're most likely to find a deal if you search for flights on Tuesdays.
Avg. deal survival time
6.8 hours
Deals from Dane County Regional Airport survive for an average of 6.8 hours. Therefore, you should book quickly when you find a deal that you like.
Rare deal frequency
14 deals
We discovered 14 rare deals for Dane County Regional Airport in the last month. These rare deals, which include mistake fares, special promotions, or ultra-discounts, received an AI Deal Score of 90+.
Average price drop
-10%
The average price drop for flights into Dane County Regional Airport is 10.2%, indicating potential savings for travelers. This suggests that waiting for price reductions could be a beneficial strategy when booking flights to this airport.
Next 4 weeks: deal forecast
Dane County Regional Airport Forecast
The forecast for Dane County Regional Airport next month shows stable prices with a slight chance of a minor increase due to seasonal travel. Travelers should book in advance to secure the best deals as prices are not expected to drop significantly.
Top 5 biggest price drops (last 3 months)
Found on February 10
São Paulo - MSN
$945 → $350
63%
Found on February 10
Mendoza - MSN
$1,160 → $492
58%
Found on February 15
Santa Fe - MSN
$1,650 → $809
51%
Found on February 11
Edinburgh - MSN
$3,400 → $1,724
49%
Found on February 11
London - MSN
$1,550 → $945
39%
Check these nearby airports too
Looking for more options? These airports near MSN sometimes drop rare deals too:
General Mitchell International (MKE)
~5 rare deals/month
Dane County Regional (MSN)
~13 rare deals/month
Chicago Rockford International (RFD)
~10 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially MKE and MSN for long-haul deal surprises.
When Is the Best Time to Fly from United States to Madison
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Madison:
Cheapest month
January
Cheapest month
January is often the cheapest month to fly to Madison, Wisconsin. The winter chill keeps the crowds away, making it a budget-friendly time to explore the city’s indoor attractions. You can enjoy cozy cafes, museums, and maybe even a snowy landscape without breaking the bank. Plus, who doesn’t love a good excuse to snuggle up with a warm drink?
Best day to book
Tuesday
Best day to book
Tuesday is your golden ticket for booking flights to Madison! Airlines often release deals early in the week to fill up those planes. By booking on Tuesday, you’re more likely to snag a sweet discount and save some cash for cheese curds and local brews.
Cheapest days to fly
Wednesday
Cheapest days to fly
Flying to Madison on Wednesday can save you some serious cheddar. Mid-week flights tend to be less popular with business travelers, driving down prices. Take advantage of the lighter crowds and lower fares to explore all that Madison has to offer, from its vibrant State Street to the scenic lakes.
Advance booking sweet spot
2 Months
Advance booking sweet spot
Booking about two months in advance hits the sweet spot for flights to Madison. This timeframe usually offers a balance between availability and affordability. Planning ahead ensures you get your preferred flight times and seats without emptying your wallet. So, mark your calendar and get ready for a Badger State adventure!
Madison Airports & Ground Transportation
One big question for travelers is which Madison airport to fly into. Here’s a quick guide to Madison’s airports and how to get to the city from each:
Dane County Regional Airport (MSN)
Welcome to MSN, your gateway to the beautiful city of Madison! This cozy airport offers a convenient and stress-free travel experience with a touch of Wisconsin charm. You'll find a variety of amenities including free Wi-Fi, charging stations, and local dining options to satisfy your pre-flight cravings. Getting to downtown Madison is a breeze, with taxis, ride-sharing services, and rental cars readily available. The airport is only 5 miles away from downtown. For a smooth ride, consider hopping on the convenient and affordable bus service that connects the airport directly to the heart of the city.
Tip: Arrive a little early to explore the local art displays showcasing Wisconsin's vibrant culture!
General Mitchell International Airport (MKE)
Just a hop, skip, and a jump away in Milwaukee, MKE offers even more flight options for your Madison adventure! While slightly further from Madison, this bustling airport provides a wider range of airlines and international connections. Inside, you'll discover a plethora of shops, restaurants, and even a museum showcasing Wisconsin's aviation history. Transportation to Madison is easily arranged with several shuttle services, car rentals, and even a convenient Amtrak train. The trip from the airport to Madison is about 80 miles.
What to Do in Madison
Madison isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Madison, organized by interest:
Sightseeing & landmarks
Madison is a city brimming with iconic landmarks and scenic views! Don't miss the Wisconsin State Capitol Building, a stunning architectural masterpiece, and take a stroll through the Olbrich Botanical Gardens for a serene escape into nature.
Arts & culture
Madison's arts scene is vibrant and diverse. Catch a show at the Overture Center for the Arts, explore the Chazen Museum of Art's impressive collections, or wander State Street to soak in the city's lively atmosphere.
Food & nightlife
Get ready for a culinary adventure in Madison! From farm-to-table restaurants to cozy pubs and energetic nightlife, there's something to satisfy every palate. Sample local cheeses, craft beers, and enjoy the city's vibrant dining scene.
Shopping & fashion
Shop 'til you drop in Madison's unique boutiques and shopping districts. Explore State Street for eclectic finds, Hilldale Shopping Center for upscale retailers, and the Dane County Farmers' Market for local goods and artisanal crafts.
Nearby getaways
Escape the city and discover the natural beauty surrounding Madison. Take a day trip to Devil's Lake State Park for hiking and stunning views, explore the charming town of New Glarus, or enjoy the scenic beauty of the Wisconsin Dells.
No matter your interest – be it art, food, nightlife, or nature – Madison has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Madison This Month
old oaks with listening party, sam ness and the other natural flavors
Listening Party, a Milwaukee-based band, has spent the last decade crafting songs that connect with audiences through their folk and Americana sound, creating a reverent and engaging musical experience.
mad city presidents cup
The Mad City Presidents Cup is an annual hockey tournament held in Sun Prairie, Wisconsin, attracting teams and fans from around the region for a weekend of competitive games.
58th annual mad city model railroad show
The Mad City Model Railroad Show features exhibits in all scales, toy trains, clinics, and vendors offering a wide selection of model railroad items. With over 300 tables, it's a must-see for train enthusiasts.
cap city cougars vs viroqua blackhawks
The Cap City Cougars face off against the Viroqua Blackhawks in a Girls Varsity/JV hockey match. Come support local high school hockey!
Madison Weather
Weather in Madison
Mon, Feb 16
10%
16° 3°
10%
Tue, Feb 17
Frequently Asked Questions About Flights to Madison
Pro Tips for Finding Cheap Flights to Madison
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Madison flights:
Be Flexible with Your Dates: Flying on Tuesdays or Wednesdays is often cheaper than weekends. Mid-week flights are like the unsung heroes of budget travel!
Consider Nearby Airports: Check flights into airports near Madison, like Milwaukee. A little extra drive time can save you some serious cash.
