A Travel Price Comparison for United States of America Winston-Salem vs. Milwaukee for Attractions, Food, Nightlife, and Families

Should you visit Winston-Salem or Milwaukee?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Winston-Salem or Milwaukee? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Winston-Salem

Winston-Salem is a welcoming, friendly, and under-rated city. Visitors also love the food, shopping, and museums.

Milwaukee

Milwaukee is a undiscovered, friendly, and welcoming city. Other popular activities here include museums, nightlife, and shopping.

Winston-Salem and Milwaukee: Pros and Cons

Pros
  • Popular museums and historical sights
  • Active nightlife
  • Scenic old town
  • Family-friendly
Things to Consider
  • Less popular with couples
Pros
  • Popular museums and historical sights
  • Active nightlife
  • Family-friendly
Things to Consider
  • Less popular with couples


Is there more to do in Winston-Salem or Milwaukee?

Travelers will generally find more things to do in Winston-Salem than Milwaukee. While Milwaukee is larger than Winston-Salem, Winston-Salem has more sights and attractions for tourists. Winston-Salem is popular for it's southern character and quaint college campuses. It is also home to Old Salem. Milwaukee is popular for its many breweries and its baseball culture.

How is Winston-Salem different from Milwaukee?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Milwaukee and Winston-Salem. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Winston-Salem or Milwaukee?

Winston-Salem
Milwaukee

For an educational experience, head to a museum or a notable sight in either Winston-Salem or Milwaukee.

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Winston-Salem. Old Salem has a nice concentration of museums and gardens. Outside of the old town you'll find several art museums like the Museum of Early Southern Decorative Arts and the Reynolda House Museum of American Art.

Milwaukee is a good place to visit if you're interested in museums or other recognizable sights. There are several unique museums like the Harley-Davidson Museum, the National Bobblehead Hall of Fame and Museum, and the Milwaukee Public Museum. There's also the Milwaukee Art Museum and the Grohmann Museum as well as outdoor sculpture parks and other cultural and historic museums.


Is the Food Better in Winston-Salem or Milwaukee? Which Destination has the Best Restaurants?

Winston-Salem
Milwaukee

Winston-Salem is a city with good options for its restaurants. However, Milwaukee is lacking in options for its restaurant scene.

Winston-Salem has a delicious restaurant scene that relies on local flavors. North Carolina barbecue is popular around town. The city is also the birthplace of Krispy Kreme donuts and during the holiday season you should sample the local Moravian Cookies.

Milwaukee may not make the list for most foodies, but you'll find what you need while you're in town. The Midwest is known for its artery clogging comfort foods, and Milwaukee is no exception. Cheese curds, fried fish, fruit dumplings, and frozen custard are all popular.

Is Winston-Salem or Milwaukee Better for Nightlife?

Winston-Salem
Milwaukee

Evening events are good in both Winston-Salem and Milwaukee.

There's a variety of activities in the evening in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.

With a handful of venues, visitors can find a fairly lively vibe in Milwaukee. You'll find a decent number of breweries around town. There are also wine bars, nightclubs, and live music venues that are worth checking out.

Is Winston-Salem or Milwaukee Better for its Old Town?

Winston-Salem
Milwaukee

Winston-Salem is a city with good options for its old town. However, Milwaukee does not have a historic old town.

Plenty of visitors enjoy exploring the old town in Winston-Salem. Nearby Old Salem is filled with historic museums, gardens, and restaurants. A ticket is required for most of the venues, but the atmosphere and architecture are charming.

Milwaukee does not have a historic old town.


Is the Shopping Better in Winston-Salem or Milwaukee?

Winston-Salem
Milwaukee

Both Winston-Salem and Milwaukee are good shopping destinations.

Many visitors go to Winston-Salem to go shopping. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.

Plenty of visitors enjoy shopping while in Milwaukee. You'll find the standard shopping centers and shopping malls around town, but if you want some more local vendors, check out the areas around the Historic Third Ward and The Village in Wauwatosa.

Is Winston-Salem or Milwaukee Better for Families?

Winston-Salem
Milwaukee

Kids will enjoy a visit to either Winston-Salem or Milwaukee.

Winston-Salem is a family-friendly place to visit. There are interactive museums like the Kaleideum science museums. There are also outdoor parks and playgrounds, kid-friendly restaurants, and a children's theater.

Milwaukee is a family-friendly city. Kids will enjoy a visit to Discovery World, which is a science center with hands-on exhibits. There's also the Milwaukee County Zoo and the Milwaukee Public Museum. Younger kids will also enjoy a stop at Betty Brinn Children's Museum.

Is Winston-Salem or Milwaukee Better for Couples?

Winston-Salem
Milwaukee

Most people don't think of either Winston-Salem or Milwaukee as a couple's destination.

Winston-Salem is not always the best place to visit for a couple. There are restaurants and movie theaters that make for a nice date night. There are also parks and walks that will get you outdoors.

Milwaukee is not the best destination for a couple to visit. Take a walk or visit a local restaurant. There are also museums and performances that make for a nice outing.


Is Winston-Salem or Milwaukee Better for Students?

Winston-Salem
Milwaukee

Winston-Salem and Milwaukee are both good destinations for students and younger travelers.

Winston-Salem is a good city to visit for students. Wake Forest University as well as colleges such as Salem College give parts of the city a collegiate vibe.

Plenty of students visit Milwaukee. It's home to a number of colleges and universities, so there is a bit of a college town vibe.

Is Winston-Salem or Milwaukee Better for Public Transit? Which Is Easier to Get Around Without a Car?

Winston-Salem
Milwaukee

Both Winston-Salem and Milwaukee offer decent public transit options.

Public transit is generally limited in Winston-Salem. There are bus routes, but they are limited in their frequency and convenience, making a car essential for most visitors.

Public transit is mostly limited in Milwaukee. There are buses that travel around town.

Is Winston-Salem or Milwaukee a more walkable city?

Winston-Salem
Milwaukee

Milwaukee is a popular place for its ease of walking around. However, Winston-Salem is a mediocre city for its walkability.

Milwaukee is a somewhat walkable city. Parts of the city are relatively compact and walkable. The most walkable neighborhoods are East Side, Riverwest, Brewers Hill, Downtown, Avenues West/Marquette, Third Ward, Walker's Point, and Bay View.

Winston-Salem is generally not a very walkable city. The downtown area is the most pedestrian-friendly part of town, but most of the city requires a car.


For even more information, also check out Is Winston-Salem Worth Visiting? and Is Milwaukee Worth Visiting?.

Should I spend more time in Milwaukee or Winston-Salem?

How long in Winston-Salem or Milwaukee?

You'll be able to find lots of things to do in Winston-Salem or Milwaukee to fill your time. You can spend a similar amount of time exploring either. However, 1-2 days is a good amount of time to spend in either destination.

Families should spend more time in Winston-Salem than Milwaukee. Because of the many family-friendly attractions and fun things to do for kids in Winston-Salem, it's a great place to visit with the whole family.

Couples should spend more time in Winston-Salem than Milwaukee. You'll find plenty of romantic sights and fun activities in Winston-Salem that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Milwaukee than Winston-Salem if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Milwaukee.


  • How many days in Winston-Salem or Milwaukee? Ideal Length of Stay
    Winston-Salem 1-2 
    Milwaukee 1-2

One day in Winston-Salem or Milwaukee?

You'll find shopping and museums around the city of Winston-Salem. One day is a great amount of time to relax and see the many things that Winston-Salem has to offer. It has many unique tourist attractions and fascinating things to do.

Many travelers enjoy the museums and nightlife when visiting the undiscovered destination of Milwaukee. Your budget might influence how long you stay. If you enjoy all that's offered here, then one day is just the right amount of time to spend here.

A weekend in Winston-Salem or Milwaukee?

You'll find museums and nightlife around the under-rated destination of Winston-Salem. This is a popular place to visit for a weekend.A weekend should give you a good understanding of everything this city has to offer. This city offers a variety of activities to choose from.

It's hard to know how much time to spend in Milwaukee. It has many unique tourist attractions and fascinating things to do. For many, it makes a great getaway for a weekend. A weekend is usually enough time to experience most activities.

Five days in Winston-Salem or Milwaukee?

Travelers enjoy the nightlife and food when visiting the friendly city of Winston-Salem. The length of your ideal trip is an individual decision. Five days is plenty of time to see everything, even with extra days to spare.

Travelers enjoy the shopping and museums when visiting the friendly destination of Milwaukee. This city offers a variety of activities to choose from. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.


A week in Winston-Salem or Milwaukee?

Winston-Salem is a popular choice for travelers. One week is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. It will give you the chance to have new experiences.

You'll find museums and nightlife around the city of Milwaukee. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.


For some great organized tour ideas, see The Best 2-Week Tours from New York City, The Best 2-Week Tours from Anchorage, The Best 2-Week Tours from San Francisco, and The Best 2-Week Tours from Los Angeles.


Which place is cheaper, Milwaukee or Winston-Salem?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Winston-Salem is $150, while the average daily cost in Milwaukee is $176. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Winston-Salem and Milwaukee in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Winston-Salem $91
    Milwaukee $99
  • Accommodation Typical double-occupancy room
    Winston-Salem $182
    Milwaukee $198
Compare Hotels in Winston-Salem and Milwaukee

Looking for a hotel in Winston-Salem or Milwaukee? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Winston-Salem


Hotels in Milwaukee


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Winston-Salem Hotel Prices and Milwaukee Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Winston-Salem $23
    Milwaukee $38

Hired Cars and Shuttles in Milwaukee

Also for Milwaukee, here are a few examples of actual transportation services:

  • Milwaukee - General Mitchell Airport One Way Transfer : $64

Is it cheaper to fly into Winston-Salem or Milwaukee?

Prices for flights to both Milwaukee and Winston-Salem change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Winston-Salem $42
    Milwaukee $52

Food Tours and Cooking Classes in Milwaukee

For Milwaukee, here are some samples of tours and activities related to meals and dining experiences:

  • Family Fun Food Tour: $80
  • Local Food Tour: $97
  • Milwaukee Walking Food Tour With Secret Food Tours: $99
  • Original Milwaukee Guided Brewery Tour with Lunch or Dinner: $139

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Winston-Salem $20
    Milwaukee $26

Tours and Activities in Winston-Salem

Some specific costs of activities, tours, and entrance tickets for Winston-Salem are as follows:

  • Carolina History & Haunts Winston-Salem Historical Ghost Tour: $26
  • Unique Scavenger Hunt Experience in Winston-Salem by Wacky Walks: $10

Tours and Activities in Milwaukee

For Milwaukee, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • Skip the Line: Museum Admission Ticket - Grohmann Museum: $5.00
  • The Grand Walk: A Self-Guided Audio Tour through Milwaukee: $6.99
  • The Grand Milwaukee Walk: A Self-Guided Audio Tour: $6.99
  • Skip the Line: North Point Lighthouse Admission Ticket: $8.21
  • Unique Scavenger Hunt Experience in Milwaukee by Operation City Quest: $10
  • Geneva Lake Shore Path: Uncover 21 miles of stories on a self-guided audio tour: $10
  • Milwaukee Brewers Baseball Game Ticket at American Family Field: $11
  • Skip The Line: Harley-Davidson Museum Admission Ticket with Audio Guided Option: $22
  • Macabre Milwaukee Walking Tour: $26
  • Shakers Original Historical Ghost Tour: $27
  • Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures: $30
  • Milwaukee Private or Public Pedal Tavern Tour : $35

Alcohol
  • Alcohol Drinks for one day
    Winston-Salem $24
    Milwaukee $33

Sample the Local Flavors in Milwaukee

Also in Milwaukee, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Sip of Milwaukee Guided Brewery Tour with Snack: $99


When we compare the travel costs of actual travelers between Winston-Salem and Milwaukee, we can see that Milwaukee is more expensive. And not only is Winston-Salem much less expensive, but it is actually a significantly cheaper destination. So, traveling to Winston-Salem would let you spend less money overall. Or, you could decide to spend more money in Winston-Salem and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Milwaukee would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Milwaukee than you might in Winston-Salem.

If you're trying to decide if either of these two destinations are within your price range, also see Is Winston-Salem Expensive? and Is Milwaukee Expensive?.


Which is Bigger, Winston-Salem or Milwaukee?

Milwaukee has a larger population, and is about 3 times larger than the population of Winston-Salem. When comparing the sizes of Winston-Salem and Milwaukee, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Winston-Salem or Milwaukee?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Winston-Salem or Milwaukee in the Summer?

Both Milwaukee and Winston-Salem during the summer are popular places to visit. Many visitors come to Winston-Salem in the summer for the family-friendly experiences. Also, most visitors come to Milwaukee for the family-friendly experiences during these months.

In July, Winston-Salem is generally a little warmer than Milwaukee. Daily temperatures in Winston-Salem average around 81°F (27°C), and Milwaukee fluctuates around 74°F (23°C).

In Milwaukee, it's very sunny this time of the year. It's quite sunny in Winston-Salem. In the summer, Winston-Salem often gets less sunshine than Milwaukee. Winston-Salem gets 273 hours of sunny skies this time of year, while Milwaukee receives 321 hours of full sun.

It rains a lot this time of the year in Winston-Salem. Winston-Salem usually gets more rain in July than Milwaukee. Winston-Salem gets 4.4 inches (112 mm) of rain, while Milwaukee receives 3.4 inches (87 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Winston-Salem 81°F (27°C) 
    Milwaukee 74°F (23°C)

Should I visit Winston-Salem or Milwaukee in the Autumn?

The autumn attracts plenty of travelers to both Winston-Salem and Milwaukee. Most visitors come to Winston-Salem for the shopping scene during these months. Also, the autumn months attract visitors to Milwaukee because of the shopping scene.

Winston-Salem is a little warmer than Milwaukee in the autumn. The daily temperature in Winston-Salem averages around 62°F (17°C) in October, and Milwaukee fluctuates around 53°F (12°C).

In Winston-Salem, it's very sunny this time of the year. Winston-Salem usually receives more sunshine than Milwaukee during autumn. Winston-Salem gets 212 hours of sunny skies, while Milwaukee receives 174 hours of full sun in the autumn.

In October, Winston-Salem usually receives more rain than Milwaukee. Winston-Salem gets 3 inches (75 mm) of rain, while Milwaukee receives 2 inches (50 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Winston-Salem 62°F (17°C) 
    Milwaukee 53°F (12°C)

Should I visit Winston-Salem or Milwaukee in the Winter?

The winter brings many poeple to Winston-Salem as well as Milwaukee. The winter months attract visitors to Winston-Salem because of the museums, the shopping scene, and the cuisine. Also, the museums, the shopping scene, and the cuisine are the main draw to Milwaukee this time of year.

It's quite cold in Milwaukee in the winter. The weather in Winston-Salem can be very cold. In the winter, Winston-Salem is much warmer than Milwaukee. Typically, the winter temperatures in Winston-Salem in January average around 40°F (4°C), and Milwaukee averages at about 21°F (-6°C).

In the winter, Winston-Salem often gets more sunshine than Milwaukee. Winston-Salem gets 169 hours of sunny skies this time of year, while Milwaukee receives 138 hours of full sun.

Winston-Salem usually gets more rain in January than Milwaukee. Winston-Salem gets 3.2 inches (82 mm) of rain, while Milwaukee receives 1.6 inches (41 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Winston-Salem 40°F (4°C) 
    Milwaukee 21°F (-6°C)

Should I visit Winston-Salem or Milwaukee in the Spring?

Both Milwaukee and Winston-Salem are popular destinations to visit in the spring with plenty of activities.

In April, Winston-Salem is generally much warmer than Milwaukee. Daily temperatures in Winston-Salem average around 61°F (16°C), and Milwaukee fluctuates around 47°F (8°C).

It's quite sunny in Milwaukee. The sun comes out a lot this time of the year in Winston-Salem. Winston-Salem usually receives more sunshine than Milwaukee during spring. Winston-Salem gets 248 hours of sunny skies, while Milwaukee receives 211 hours of full sun in the spring.

In April, Winston-Salem usually receives more rain than Milwaukee. Winston-Salem gets 3.1 inches (80 mm) of rain, while Milwaukee receives 2.8 inches (70 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Winston-Salem 61°F (16°C) 
    Milwaukee 47°F (8°C)

Typical Weather for Milwaukee and Winston-Salem

Winston-Salem Milwaukee
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 40°F (4°C) 3.2 inches (82 mm) 21°F (-6°C) 1.6 inches (41 mm)
Feb 43°F (6°C) 3.4 inches (86 mm) 26°F (-4°C) 1.1 inches (29 mm)
Mar 52°F (11°C) 3.7 inches (94 mm) 36°F (2°C) 2.2 inches (57 mm)
Apr 61°F (16°C) 3.1 inches (80 mm) 47°F (8°C) 2.8 inches (70 mm)
May 69°F (21°C) 3 inches (77 mm) 58°F (14°C) 2.9 inches (73 mm)
Jun 77°F (25°C) 3.9 inches (99 mm) 68°F (20°C) 3.6 inches (91 mm)
Jul 81°F (27°C) 4.4 inches (112 mm) 74°F (23°C) 3.4 inches (87 mm)
Aug 80°F (26°C) 4.3 inches (109 mm) 72°F (22°C) 2.7 inches (68 mm)
Sep 73°F (23°C) 3.5 inches (90 mm) 65°F (18°C) 3 inches (77 mm)
Oct 62°F (17°C) 3 inches (75 mm) 53°F (12°C) 2 inches (50 mm)
Nov 53°F (12°C) 2.6 inches (67 mm) 41°F (5°C) 2 inches (51 mm)
Dec 44°F (7°C) 3.1 inches (80 mm) 27°F (-3°C) 1.7 inches (44 mm)