16 Best Weekend Getaways from Madison, Wisconsin (within a 4-hour flight)
- Jordan Hinsch
- Aug 25
- 7 min read
Madison, Wisconsin, is the vibrant capital city known for its picturesque lakes, thriving cultural scene, and the prestigious University of Wisconsin-Madison. Nestled between Lake Mendota and Lake Monona, it offers a perfect blend of natural beauty, diverse dining options, and a lively arts community. With its bike-friendly streets and strong emphasis on sustainability, Madison is a hub for innovation, education, and Midwestern charm.
If you're a local and looking to escape for a weekend, keep reading. With a vast array of short domestic destinations, there are also some international destinations within reach. Here are some weekend getaway ideas for locals in the Madison, Wisconsin, area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.
Orlando, Florida (MCO) - 2 Hour 46 Minute Flight
Why go?
Theme parks. Disney & Universal. Bring bug spray and an umbrella if you go during the summer. It's not my favorite city, but there's a reason why it's the #1 tourism city year after year in the US.
What to do?
Click here to view The BEST Things to Do in Orlando
When to go?
Year-Round
Who can fly you there?
United from ORD - See flight deals
Spirit from ORD - See flight deals
Frontier from ORD - See flight deals
How much will it cost to get there?
Airfare: $35+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 3 Hour 5 Minute Flight
Why go?
Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.
What to do?
Click here to view The BEST Things to Do in Miami
When to go?
Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.
Who can fly you there?
Spirit from ORD - See flight deals
How much will it cost to get there?
Airfare: $49+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.
Atlanta, Georgia (ATL) - 1 Hour 59 Minute Flight
Why go?
Brew pubs, art, nightlife, Mexican food.
What to do?
Click here to view The BEST Things to Do in Atlanta
When to go?
Year-round
Who can fly you there?
Delta from MSN - See flight deals
How much will it cost to get there?
Airfare: $19+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
New Orleans, Louisiana (MSY) - 2 Hour 27 Minute Flight
Why go?
Jazz music, other music, culture, architecture, partying, passionate football fans.
What to do?
Click here to view The BEST Things to Do in New Orleans
When to go?
Spring, Summer, Fall
Who can fly you there?
United from ORD - See flight deals
Spirit from ORD - See flight deals
How much will it cost to get there?
Airfare: $32+
Where can you stay?
Who will pick you up?
Pro Tip:
Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.
Washington, DC (IAD, DCA, BWI) - 1 Hour 51 Minute Flight
Why go?
Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.
What to do?
Click here to view The BEST Things to Do in Washington DC
When to go?
Year-round (spring season for cherry blossoms)
Who can fly you there?
American from MSN - See flight deals
How much will it cost to get there?
Airfare: $80+
Where can you stay?
Who will pick you up?
Pro Tip:
For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.
Denver, Colorado (DEN) - 2 Hour 54 Minute Flight
Why go?
Mountains, beer, National Parks, hiking, clean city, nice people.
What to do?
Click here to view The BEST Things to Do in Denver
When to go?
Year-round. Ski in the winter. Hike in the summer.
Who can fly you there?
United from MSN - See flight deals
Frontier from MSN - See flight deals
How much will it cost to get there?
Airfare: $19+
Where can you stay?
Who will pick you up?
Toronto, Ontario (YYZ, YTZ) - 1 Hour 35 Minute Flight
Why go?
Food, people, cleanliness, Hockey Hall of Fame.
What to do?
Click here to view The BEST Things to Do in Toronto
When to go?
Summer
Who can fly you there?
Air Canada from ORD - See flight deals
United from ORD - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $101+
Where can you stay?
Who will pick you up?
Chicago, Illinois (ORD, MDW) - 1 Hour 5 Minute Flight
Why go?
Food, bars, sports, rivers!
What to do?
Click here to view The BEST Things to Do in Chicago
When to go?
Summer
Who can fly you there?
United from MSN - See flight deals
American from MSN - See flight deals
How much will it cost to get there?
Airfare: $123+
Where can you stay?
Who will pick you up?
Pro Tip:
For bourbon enthusiasts, visit Untitled Supper Club on W Kinzie for an incredible speakeasy experience.
Austin, Texas (AUS) - 2 Hour 50 Minute Flight
Why go?
Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!
What to do?
Click here to view The BEST Things to Do in Austin
When to go?
Year-Round
Who can fly you there?
Frontier from ORD - See flight deals
Southwest from ORD - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $49+
Where can you stay?
Who will pick you up?
Nashville, Tennessee (BNA) - 1 Hour 30 Minute Flight
Why go?
Music (not just country), endless bars, brewpubs, hot chicken.
What to do?
Click here to view The BEST Things to Do in Nashville
When to go?
Spring, Summer and Fall
Who can fly you there?
United from ORD - See flight deals
Southwest from ORD - See flight deals
Frontier from ORD - See flight deals
How much will it cost to get there?
Airfare: $19+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Charleston, South Carolina (CHS) - 2 Hour 2 Minute Flight
Why go?
History, culture, family-friendly attractions, and water sports.
What to do?
Click here to view The BEST Things to Do in Charleston
When to go?
Spring, Summer and Fall
Who can fly you there?
American from ORD - See flight deals
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $140+
Where can you stay?
Who will pick you up?
Asheville, North Carolina (AVL) - 1 Hour 42 Minute Flight
Why go?
Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!
What to do?
Click here to view The BEST Things to Do in Asheville
When to go?
Spring, Summer and Fall
Who can fly you there?
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $90+
Where can you stay?
Who will pick you up?
Salt Lake City, Utah (SLC) - 3 Hour 34 Minute Flight
Why go?
Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.
What to do?
Click here to view The BEST Things to Do in Salt Lake City
When to go?
Year-Round
Who can fly you there?
Delta from ORD - See flight deals
American from ORD - See flight deals
Frontier from ORD - See flight deals
How much will it cost to get there?
Airfare: $53+
Where can you stay?
Who will pick you up?
Charlotte, North Carolina (CLT) – 1 Hour 57 Minute Flight
Why go?
Diverse Cultural Attractions, Thriving Food Scene, Outdoor Activities, Sports Hub, Historical Significance, Shopping, Festivals and Events.
What to do?
Click here to view The BEST Things to Do in Charlotte
When to go?
The best times to visit Charlotte are March–May and September–November.
Who can fly you there?
Frontier from ORD - See flight deals
American from ORD - See flight deals
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $19+
Where can you stay?
Who will pick you up?
Aspen, Colorado (ASE) - 3 Hour 18 Flight
Why go?
Skiing, great scenery, luxury.
What to do?
Click here to view The BEST Things to Do in Aspen
When to go?
Year-round
Who can fly you there?
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $283+
Where can you stay?
Who will pick you up?
Pro Tip:
It's very expensive, but worth a shot. 3.5 hour drive from Denver if you wish to save some $$.
Kansas City, Missouri (MCI) - 1 Hour 34 Minute Flight
Why go?
BBQ! BBQ! BBQ!
What to do?
Click here to view The BEST Things to Do in Kansas City
When to go?
Year-round
Who can fly you there?
United from ORD - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $123+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.
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