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

Should you visit Winston-Salem or Chicago?

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

Should I visit Winston-Salem or Chicago? 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 friendly, under-rated, and welcoming city. Other popular activities here include shopping, museums, and nightlife.

Chicago

Chicago is a cosmopolitan, diverse, and vibrant city. Visitors will also find so much to do here because it's a large city with many sights and attractions. It offers plenty of beauty for visitors. Other popular activities here include museums, theater, and nightlife.

Winston-Salem and Chicago: Pros and Cons

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

Tourists will generally find more to do in Chicago than Winston-Salem. It is bigger and it has more sights, attractions, and activities for travelers. Chicago is very popular for its museums, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, big city activities, and impressive beauty, while Winston-Salem attracts visitors for its historical sights. Chicago is more touristy than Winston-Salem and is known for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also well known for The Willis Tower (previously the Sears Tower). Winston-Salem is famous for it's southern character and quaint college campuses.

How is Winston-Salem different from Chicago?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Chicago 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 Chicago?

Chicago is renowned for its sights and museums. Also, Winston-Salem is not as famous, but is still a good city to visit for its museums and history.

You'll find many recognizable landmarks that put Chicago on the map. There are countless landmarks, museums, and iconic sights in the area. Some of the most famous are the Art Institute of Chicago, Adler Planetarium, and the Museum of Science and Industry. Notable landmarks include the famous Willis Tower - formerly the Sears Tower, Buckingham Fountain, and the iconic Cloud Gate (the bean).

Winston-Salem is a good place to visit if you're interested in museums or other recognizable sights. 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.

Is Winston-Salem or Chicago Better for Theater?

Chicago is renowned for its shows and theatre. However, Winston-Salem is not a theatre destination.

The theater and performance venues in Chicago draw crowds from around the world. Theater is big here with many of the major Broadway productions visiting the city. There is also an endless list of smaller, local theaters to choose from.

Winston-Salem is not a theatre destination.

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

Chicago is renowned for its local cuisine and restaurants. Also, Winston-Salem is not as famous, but is still a good city to visit for its restaurants.

For foodies, Chicago is an obvious choice, as it is one of the food capitals of the world. With everything from award-winning luxury restaurants to local dives, this city has something for everyone. It also has very distinct local flavors and dishes that create an identity and bring great pride to the locals. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

There are plenty of up and coming restaurants around Winston-Salem. 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.

Is Winston-Salem or Chicago Better for Nightlife?

Chicago is renowned for its evening party scene. Also, Winston-Salem is not as famous, but is still a good city to visit for nightlife.

Chicago is a destination that you simply have to visit at least once for nightlife. It has a wide range of activities at night, with everything from theater and comedy clubs to dance venues, sporting events, and local bars. It's easy to fill many evenings with whatever activity appeals to you. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

With a handful of venues, visitors can find a fairly lively vibe in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.

Is Winston-Salem or Chicago Better for Music?

Chicago is renowned for its music scene. However, Winston-Salem is not a live music destination.

In Chicago you'll find nightly musicians performing at a variety of venues. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Winston-Salem is not a live music destination.

Is Winston-Salem or Chicago Better for Beaches?

Chicago is a popular place for the beach. However, Winston-Salem is not a beach destination.

Chicago is a good option for a beach vacation. While you don't immediately think of beaches when you think of Chicago, there are some nice beaches by the lake. If the weather is nice, it's a great area to spend some time.

Winston-Salem is not a beach destination.

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

Winston-Salem is very good for its historic old town charm. However, Chicago does not have a historic old town.

Winston-Salem offers a nice historic old town area. 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.

Chicago does not have a historic old town.

Is the Shopping Better in Winston-Salem or Chicago?

Chicago is renowned for its shopping areas. Also, Winston-Salem is not as famous, but is still a good city to visit for shopping.

Chicago is a world class destination for shoppers. There are countless neighborhoods that are filled with boutiques, local vendors, and art galleries. The city has some of the country's best shopping opportunities, and the most notable area is the famous Michigan Avenue and the Magnificent Mile.

Plenty of visitors enjoy shopping while in Winston-Salem. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.

Is Winston-Salem or Chicago Better for Christmas?

Chicago is notable for its Christmas activities. However, Winston-Salem does not offer Christmas activities.

Chicago is an extremely popular place to visit during the Christmas season. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Winston-Salem does not offer Christmas activities.

Is Winston-Salem or Chicago Better for Christmas Markets?

Chicago is a popular place for its Christmas markets. However, Winston-Salem does not offer Christmas markets.

Many visitors go to the Christmas markets in Chicago. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Winston-Salem does not offer Christmas markets.

Is Winston-Salem or Chicago Better for Families?

Chicago is renowned for its family-friendly activities. Also, Winston-Salem is not as famous, but is still a good city to visit for its kid-friendly activities.

As it has a large number of activities for kids, Chicago is a very family-friendly destination. The city has a large number of activities for kids, including zoos, Shedd Aquarium, impressive children's museums, and large and elaborate playgrounds in Millennium Park. It's easy to keep kids entertained in this very kid-focused city.

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

Is Winston-Salem or Chicago Better for Couples?

Chicago is a popular place for couples. However, Winston-Salem is a mediocre city for romance.

Chicago is a good city for couples to visit. Couples will enjoy exploring the city's vibrant theater scene and diverse neighborhoods. There are many varied restaurants and entertainment options that make for a great date night. There are also sporting events, parks, and gardens where couples can explore.

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

Is Winston-Salem or Chicago Better for Backpackers and Budget Travelers?

Chicago is a popular place for backpackers. However, Winston-Salem is a mediocre city for backpackers and budget travelers.

Plenty of budget travelers visit Chicago. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Winston-Salem is not the best destination for backpackers and budget travelers due to its high prices. It's not on the itinerary for most backpackers.

Is Winston-Salem or Chicago Better for Students?

Chicago is renowned for students. Also, Winston-Salem is not as famous, but is still a good city to visit for its student-friendly activities.

Many students frequent Chicago. The city has a large number of universities that bring in students from around the country and around the globe. It's a huge international city with economic ties and many opportunities connected to the universities.

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

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

Chicago is renowned for its public transit. However, Winston-Salem is a mediocre city for times when you don't have a car.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

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

Is Winston-Salem or Chicago a more walkable city?

Chicago is notable for its ease of walking around. However, Winston-Salem is a mediocre city for its walkability.

Chicago is a very walkable destination. The city has many restaurants, sights, and hotels that are easily accessible on foot.

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 Chicago Worth Visiting?.

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

How long in Winston-Salem or Chicago?

In either Winston-Salem or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Chicago than Winston-Salem because of the overall number of sights and activities. Usually, 1-2 days is a good amount of time for Winston-Salem, and 3-5 days is enough time in Chicago.

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

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

Backpackers and budget travelers should spend more time in Chicago 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 Chicago.

One day in Winston-Salem or Chicago?

In Winston-Salem, you'll find nightlife and food. This city offers something for everyone. This would be the perfect place to spend one day, as it has just the right amount of activities.

Chicago is a bustling city that offers something for everyone. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.

A weekend in Winston-Salem or Chicago?

In Winston-Salem, you'll find food and shopping. The length of your trip often depends on your style of travel. A weekend here is typical. A weekend is a great amount of time to relax and see the many things that Winston-Salem has to offer.

It's hard to know how much time to spend in Chicago. It has many unique tourist attractions and fascinating things to do. A weekend is usually not enough time for a trip here as there is plenty to do.

Five days in Winston-Salem or Chicago?

Winston-Salem is a great place to explore. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

Chicago is a bustling city that offers something for everyone. This city offers a variety of activities to choose from. If you have five days, this is a great place to go. Five days is usually enough time to experience most activities.

A week in Winston-Salem or Chicago?

It's hard to know how much time to spend in Winston-Salem. Many people enjoy the museums and nightlife when visiting Winston-Salem. One week may feel like too much time unless you plan to do a lot of relaxing.

You'll find theater and nightlife around the city of Chicago. 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 Romantic Tours for Couples in United States of America, The Best Polar Tours & Cruises in United States of America, The Best Walking Tours in United States of America, and The Best Tours Under $1000 in United States of America.

When we compare the travel costs of actual travelers between Winston-Salem and Chicago, we can see that Chicago 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 Chicago would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Chicago 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 Chicago Expensive?.

Which is Bigger, Winston-Salem or Chicago?

Chicago has a larger population, and is about 10 times larger than the population of Winston-Salem. When comparing the sizes of Winston-Salem and Chicago, 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 Chicago?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

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

The summer attracts plenty of travelers to both Winston-Salem and Chicago. The family-friendly experiences are the main draw to Winston-Salem this time of year. Also, many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.

Winston-Salem is around the same temperature as Chicago in the summer. The daily temperature in Winston-Salem averages around 81°F (27°C) in July, and Chicago fluctuates around 77°F (25°C).

People are often attracted to the plentiful sunshine in Chicago this time of the year. In Winston-Salem, it's very sunny this time of the year. Winston-Salem usually receives less sunshine than Chicago during summer. Winston-Salem gets 273 hours of sunny skies, while Chicago receives 326 hours of full sun in the summer.

Chicago receives a lot of rain in the summer. Winston-Salem gets a good bit of rain this time of year. In July, Winston-Salem usually receives more rain than Chicago. Winston-Salem gets 4.4 inches (112 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.

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

The autumn brings many poeple to Winston-Salem as well as Chicago. Many travelers come to Winston-Salem for the shopping scene. Also, many visitors come to Chicago in the autumn for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In the autumn, Winston-Salem is a little warmer than Chicago. Typically, the autumn temperatures in Winston-Salem in October average around 62°F (17°C), and Chicago averages at about 56°F (14°C).

People are often attracted to the plentiful sunshine in Winston-Salem this time of the year. In the autumn, Winston-Salem often gets more sunshine than Chicago. Winston-Salem gets 212 hours of sunny skies this time of year, while Chicago receives 195 hours of full sun.

Winston-Salem usually gets more rain in October than Chicago. Winston-Salem gets 3 inches (75 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year.

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

Both Chicago and Winston-Salem are popular destinations to visit in the winter with plenty of activities. Many visitors come to Winston-Salem in the winter for the museums, the shopping scene, and the cuisine. Also, most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.

Chicago can be very cold during winter. Winston-Salem can get quite cold in the winter. In January, Winston-Salem is generally much warmer than Chicago. Daily temperatures in Winston-Salem average around 40°F (4°C), and Chicago fluctuates around 25°F (-4°C).

Winston-Salem usually receives more sunshine than Chicago during winter. Winston-Salem gets 169 hours of sunny skies, while Chicago receives 134 hours of full sun in the winter.

In January, Winston-Salem usually receives more rain than Chicago. Winston-Salem gets 3.2 inches (82 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.

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

Both Chicago and Winston-Salem during the spring are popular places to visit. Furthermore, the spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.

Winston-Salem is a little warmer than Chicago in the spring. The daily temperature in Winston-Salem averages around 61°F (16°C) in April, and Chicago fluctuates around 52°F (11°C).

In Chicago, it's very sunny this time of the year. It's quite sunny in Winston-Salem. In the spring, Winston-Salem often gets more sunshine than Chicago. Winston-Salem gets 248 hours of sunny skies this time of year, while Chicago receives 218 hours of full sun.

Chicago gets a good bit of rain this time of year. Winston-Salem usually gets less rain in April than Chicago. Winston-Salem gets 3.1 inches (80 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year.

Typical Weather for Chicago and Winston-Salem