Milwaukee, Wisconsin, a bustling city on the shores of Lake Michigan, is celebrated for its rich brewing heritage, vibrant cultural scene, and welcoming Midwestern charm. Known as the "Brew City," Milwaukee has a storied history with beer, home to iconic breweries like Miller and a thriving craft beer scene. The city's cultural landscape is diverse, featuring institutions such as the Milwaukee Art Museum with its striking architecture, the historic Pabst Theater, and the Milwaukee Public Market. Festivals are a cornerstone of Milwaukee's community life, with events like Summerfest, the world's largest music festival, drawing crowds each year. The city's neighborhoods offer a mix of historic and modern attractions, from the historic Third Ward with its boutiques and eateries to the scenic Riverwalk. Milwaukee's culinary scene is diverse, offering everything from traditional German fare to contemporary farm-to-table cuisine. With its blend of historical richness, cultural vibrancy, and scenic beauty, Milwaukee provides a dynamic and inviting atmosphere for residents and visitors alike.
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 Milwaukee, 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.
Denver, Colorado (DEN) - 2 Hour 45 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 MKE - See flight deals
Southwest from MKE - See flight deals
Frontier from MKE - See flight deals
How much will it cost to get there?
Airfare: $20+
Where can you stay?
Who will pick you up?
New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour 10 Minute Flight
Why go?
It might not be the same city it was before, but it'll always make for a great weekend getaway.
What to do?
Click here to view The BEST Things to Do in New York
When to go?
Summer for the best weather, but you’ll pay peak rates for solid hotels.
Winter for Christmas festivities!
Who can fly you there?
AA from MKE - See flight deals
Delta from MKE - See flight deals
United from MKE - See flight deals
Spirit Airways from ORD - See flight deals
JetBlue from MKE - See flight deals
Southwest from MKE - See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?
Who will pick you up?
Boston, Massachusetts (BOS) - 2 Hour 15 Minute Flight
Why go?
History and cool summertime temps!
What to do?
Click here to view The BEST Things to Do in Boston
When to go?
Summer for the best weather, but peak rates for solid hotels.
Who can fly you there?
Delta from MKE - See flight deals
JetBlue from MKE - See flight deals
Southwest from MKE - See flight deals
How much will it cost to get there?
Airfare: $80+
Where can you stay?
Who will pick you up?
Orlando, Florida (MCO) - 3 Hour 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?
Allegiant from ORD - See flight deals
Spirit Airways from ORD - See flight deals
Frontier from ORD - See flight deals
Southwest from ORD - See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 3 Hour 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?
AA from ORD - See flight deals
Spirit Airways from ORD - See flight deals
Southwest from ORD - See flight deals
How much will it cost to get there?
Airfare: $40+
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.
Washington, DC (IAD, DCA, BWI) - 2 Hour 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?
Southwest from MKE - See flight deals
AA from MKE - See flight deals
Allegiant from MKE - See flight deals
United from MKE - See flight deals
How much will it cost to get there?
Airfare: $90+
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.
Atlanta, Georgia (ATL) - 2 Hour 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 ORD - See flight deals
Southwest from ORD - See flight deals
How much will it cost to get there?
Airfare: $30+
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 30 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
Frontier from ORD - See flight deals
Southwest from ORD - See flight deals
How much will it cost to get there?
Airfare: $20+
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.
Toronto, Ontario (YYZ, YTZ) - 1 Hour 30 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
WestJet from ORD - See flight deals
Swoop from ORD - See flight deals
Flair Airlines from ____ - See flight deals
How much will it cost to get there?
Airfare: $100+
Where can you stay?
Who will pick you up?
Philadelphia, Pennsylvania (PHL) - 2 Hour Flight
Why go?
History, sports, cheesesteaks
What to do?
Click here to view The BEST Things to Do in Philadelphia
When to go?
Summer and Fall
Who can fly you there?
AA from ORD - See flight deals
Spirit Airlines from ORD - See flight deals
Southwest from ORD - See flight deals
Frontier Airlines from ORD - See flight deals
How much will it cost to get there?
Airfare: $20+
Where can you stay?
Who will pick you up?
Austin, Texas (AUS) - 2 Hour 45 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?
AA from ORD - See flight deals
Southwest from ORD - See flight deals
How much will it cost to get there?
Airfare: $200+
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: $80+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Montreal, Quebec (YUL) - 2 Hour Flight
Why go?
More restaurants per capita than any other North American city.
What to do?
Click here to view The BEST Things to Do in Montreal
When to go?
Summer
Who can fly you there?
AA from ORD - See flight deals
Delta from ORD - See flight deals
United Airlines from ORD - See flight deals
Air Canada from ORD - See flight deals
How much will it cost to get there?
Airfare: $150+
Where can you stay?
Who will pick you up?
Cancun & Tulum, Mexico (CUN) - 3 Hour 30 Minute Flight
Why go?
Your money goes a long way in Cancun: all-inclusive hotels, nightlife, and activities.
Your money doesn’t go very far in Tulum: boutique hotels (some are grossly overpriced), many hotels have no air conditioning, taxis and bike rentals will try to rip you off.
If you’re looking for clubs and nightlife, go to Tulum Beach.
If you’re looking for culture and less expensive eats, go to Tulum Centro.
Tulum is actually a great experience if you have the right mindset going into your vacation.
What to do?
Click here to view The BEST Things to Do in Cancun
Click here to view The BEST Things to Do in Tulum
When to go?
December to April for the best weather.
Avoid March Spring Break travel if you want to be at peace.
Who can fly you there?
Spirit Airways from ORD - See flight deals
How much will it cost to get there?
Airfare: $200+
Where can you stay?
Who will pick you up?
Charleston, South Carolina (CHS) - 2 Hour 20 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?
AA from ORD - See flight deals
How much will it cost to get there?
Airfare: $150+
Where can you stay?
Who will pick you up?
Asheville, North Carolina (AVL) - 2 Hour 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?
AA from ORD - See flight deals
How much will it cost to get there?
Airfare: $250+
Where can you stay?
Who will pick you up?
Calgary, Alberta (YYC) - 3 Hour 30 Minute Flight
Why go?
Calgary is a vibrant city that serves as a gateway to the majestic Rocky Mountains, offering a dynamic mix of modern attractions, rich cultural festivals, and immediate access to outdoor adventures.
What to do?
Click here to view The BEST Things to Do in Calgary
When to go?
Summer
Who can fly you there?
Air Canada 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 25 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
How much will it cost to get there?
Airfare: $250+
Where can you stay?
Who will pick you up?
Charlotte, North Carolina (CLT) – 2 Hour 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
AA from ORD - See flight deals
How much will it cost to get there?
Airfare: $90+
Where can you stay?
Who will pick you up?
