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

Should you visit Williamsburg or Chicago?

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

Which city should you visit? Read on to compare the activities as well as the prices of travel for Williamsburg and Chicago. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Williamsburg

Williamsburg is a quaint, well-preserved, and historic town. Williamsburg offers plenty of beauty for visitors. Other popular activities here include museums, food, and shopping. See Williamsburg travel costs.

Chicago

Chicago is a edgey, cosmopolitan, and diverse city. Visitors will also find so much to do here because it's a large city with many sights and attractions. Chicago offers plenty of beauty for visitors. Other popular activities here include live music, food, and beaches. See Chicago travel costs.

Williamsburg and Chicago: Pros and Cons

Is there more to do in Williamsburg or Chicago?

Travelers will usually find more to do in Chicago. Although Williamsburg and Chicago are popular destinations, Chicago has more sights and attractions for tourists. Chicago is very popular for its museums and attractions, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, and big city activities, while Williamsburg attracts visitors for its historical sights. Williamsburg is famous for its historic and colonial charm, its award winning amusement parks, and its historical reenactments. Chicago is famous 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).

How is Williamsburg different from Chicago?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Williamsburg or Chicago?

Chicago is a world-class destination for its museums and landmarks. Also, Williamsburg is still popular, but not quite as popular for its historical sights.

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).

Williamsburg offers many unique museums, sights, and landmarks that will make for a memorable trip. Colonial Williamsburg is like a living museum with reenactments and historic buildings that date back to the colonial days. In addition to the historic area, there are folk art museums and other historic sights in the area.

Is Williamsburg or Chicago Better for Theater?

Chicago is a world-class destination for its shows and theatre. However, Williamsburg is not a theatre destination.

Chicago is considered to be a world-class theater destination. 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.

Williamsburg is not a theatre destination.

Is the Food Better in Williamsburg or Chicago? Which Destination has the Best Restaurants?

Chicago is a world-class destination for its restaurant scene. Also, Williamsburg is still popular, but not quite as popular for its local flavors and cuisine.

Eat your way through Chicago, as it has many local or world renowned restaurants to choose from. 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.

The food selection at local restaurants is excellent in Williamsburg. Head to Historic Williamsburg if you want to try some colonial classics. There are historic taverns that maintain their old world charm and serve dishes such as peanut soup and stewed beef. Around town you'll also find casual restaurants with pizza, macaroni and cheese, and burgers.

Is Williamsburg or Chicago Better for Nightlife?

Chicago is a world-class destination for its evening party scene. However, Williamsburg is a town with minimal options for nightlife.

People head to Chicago just to party. 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.

Williamsburg doesn't have the most active nightlife scene. Despite its student population, there isn't much of a nightlife scene in town. There are restaurants where you can enjoy fine wine or cocktails, but nightclubs and bars are limited.

Is Williamsburg or Chicago Better for Music?

Chicago is a world-class destination for its music scene. However, Williamsburg 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.

Williamsburg is not a live music destination.

Is Williamsburg or Chicago Better for Beaches?

Chicago is a good destination for the beach. However, Williamsburg is not a beach destination.

Chicago offers a nice beach destination. 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.

Williamsburg is not a beach destination.

Is Williamsburg or Chicago Better for its Old Town?

Williamsburg is renowned for its historic old town charm. However, Chicago does not have a historic old town.

The old town of Williamsburg is one of the most recognized in the world. Colonial Williamsburg is an impressively maintained area with museums, shops, and taverns. There are live reenactments of historic events as well as blacksmiths, wig shops, and carriage rides. You can wander around without a ticket, but for access to many parts of the historic area you'll need to purchase a pass.

Chicago does not have a historic old town.

Is the Shopping Better in Williamsburg or Chicago?

Chicago is a world-class destination for its shopping areas. Also, Williamsburg is still popular, but not quite as popular 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.

Shopping is a popular activity when visiting Williamsburg. Charming shops both in the historic area and just outside sell unique items that reflect the city's past. There are souvenirs, food items, cookbooks, and home decor to choose from.

Is Williamsburg or Chicago More Beautiful?

You'll find a similar quality of nice scenery and beauty in both Williamsburg and Chicago.

Williamsburg offers plenty of beauty for visitors. The area's colonial architecture gives it a historic and traditional beauty that appeals to visitors and residents alike.

Chicago is a gorgeous place to visit. The water makes this city a truly unique place to explore, and the world class architecture is not to be missed.

Is Williamsburg or Chicago Better for Families?

Both Williamsburg and Chicago are first-rate family-friendly destinations.

With a huge array of activities for kids, Williamsburg is very family-friendly. Older kids will appreciate the history in the area. For kids of all ages there are a number of amusement parks and water parks such as Great Wolf Lodge, Busch Gardens, and the award winning Water Country USA.

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.

Is Williamsburg or Chicago Better for Couples?

Williamsburg is a great destination for couples. Also, Chicago is still popular, but not quite as popular for romance.

Couples visit Williamsburg frequently as it offers plenty of romantic activities. Historic Williamsburg is filled with inns and charming restaurants that make this a beautiful destination for couples. There are quaint restaurants that serve colonial food and interesting southern shops with unique trinkets. You can also wander around the campus of William and Mary College.

Chicago is a nice destination for couples. 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.

Is Williamsburg or Chicago Better for Backpackers and Budget Travelers?

Chicago is a good destination for backpackers. However, Williamsburg is a town with minimal options for backpackers and budget travelers.

Plenty of backpackers 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.

Williamsburg is a challenging destination for budget travelers and backpackers due to the higher prices. There's a number of restaurants and bars that cater to the student population, but there's little else that attracts backpackers.

Is Williamsburg or Chicago Better for Students?

Williamsburg and Chicago are first-rate places to visit for students.

Williamsburg is a very popular place to visit for students. The College of William and Mary has a beautiful campus and students enjoy the charming atmosphere with colonial architecture around town. There are also good restaurants and a great collegiate vibe.

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.

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

Chicago is a world-class destination for its public transit. However, Williamsburg is a town with minimal options for times when you don't have a car.

With a huge network, the transit system in Chicago can get you around easily. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is mostly limited in Williamsburg. There are buses around town, and they offer access to Historic Williamsburg, but for most places you'll need to have your own car.

Is Williamsburg or Chicago a more walkable city?

Chicago is a great destination for its ease of walking around. However, Williamsburg is a town with minimal options for its walkability.

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

Williamsburg is generally not a very walkable town. Historic Williamsburg and the neighborhoods around the College of William and Mary are all walkable, but if you plan to visit the amusement parks then you'll absolutely need a car.

For even more information, also check out Is Williamsburg Worth Visiting? and Is Chicago Worth Visiting?.

Should I spend more time in Chicago or Williamsburg?

How long in Williamsburg or Chicago?

In either Williamsburg or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Chicago than Williamsburg because of the overall number of sights and activities. Usually, 2-4 days is a good amount of time for Williamsburg, and 3-5 days is enough time in Chicago.

Families should spend more time in Chicago than Williamsburg. 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 Williamsburg. 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 Williamsburg 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 Williamsburg or Chicago?

In Williamsburg, you'll find museums and food. Most visitors spend time around the old town while in the area. This town offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

Each neighborhood in Chicago has its own distinct appeal, so there are pleny of areas to explore. The length of your ideal trip is an individual decision. With so much to do, one day is probably not enough time to see everything.

A weekend in Williamsburg or Chicago?

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

Chicago is a fun place to experience. It will give you the chance to have new experiences. But since there are so many activities, you'll likely want to spend more than a weekend exploring.

Five days in Williamsburg or Chicago?

Williamsburg is a great place to explore. The old town is one of the main draws for visitors. 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.

Each neighborhood in Chicago has its own distinct appeal, so there are pleny of areas to explore. Take your pick from the many activities offered here. Plenty of people spend five days in the area when traveling. So, five days is just the right amount of time to spend here.

A week in Williamsburg or Chicago?

It's hard to know how much time to spend in Williamsburg. Many people enjoy the museums and food when visiting Williamsburg. Exploring the old town is a popular activity. One week may feel like too much time unless you plan to do a lot of relaxing.

Chicago is a popular place to visit. One week may feel like too much time unless you plan to do a lot of relaxing. The entire region has so many activities, and you'll want time to do everything.

For some great organized tour ideas, see The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, The Best Historical Tours in United States of America, and The Best 10-Day Tours in United States of America.

When we compare the travel costs of actual travelers between Williamsburg and Chicago, we can see that Chicago is more expensive. And not only is Williamsburg much less expensive, but it is actually a significantly cheaper destination. So, traveling to Williamsburg would let you spend less money overall. Or, you could decide to spend more money in Williamsburg 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 Williamsburg.

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

Which is Bigger, Williamsburg or Chicago?

Chicago has a larger population, and is about 250 times larger than the population of Williamsburg. When comparing the sizes of Williamsburg 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 Williamsburg 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 Williamsburg or Chicago in the Summer?

Both Chicago and Williamsburg are popular destinations to visit in the summer with plenty of activities. Many travelers come to Williamsburg for the family-friendly experiences. Also, many visitors come to Chicago in the summer for the beaches, the city activities, the music scene, and the family-friendly experiences.

Williamsburg is around the same temperature as Chicago in the summer. The daily temperature in Williamsburg averages around 78°F (26°C) in July, and Chicago fluctuates around 77°F (25°C).

It's quite sunny in Chicago. The sun comes out a lot this time of the year in Williamsburg. Williamsburg usually receives less sunshine than Chicago during summer. Williamsburg gets 279 hours of sunny skies, while Chicago receives 326 hours of full sun in the summer.

It rains a lot this time of the year in Chicago. It's quite rainy in Williamsburg. In July, Williamsburg usually receives more rain than Chicago. Williamsburg gets 4.7 inches (120 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.

Should I visit Williamsburg or Chicago in the Autumn?

Both Chicago and Williamsburg during the autumn are popular places to visit. Many visitors come to Williamsburg in the autumn for the shopping scene and the natural beauty of the area. Also, most visitors come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area during these months.

In the autumn, Williamsburg is a little warmer than Chicago. Typically, the autumn temperatures in Williamsburg in October average around 61°F (16°C), and Chicago averages at about 56°F (14°C).

It's quite sunny in Williamsburg. In the autumn, Williamsburg often gets more sunshine than Chicago. Williamsburg gets 211 hours of sunny skies this time of year, while Chicago receives 195 hours of full sun.

Williamsburg usually gets more rain in October than Chicago. Williamsburg gets 2.8 inches (71 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year.

Should I visit Williamsburg or Chicago in the Winter?

The winter attracts plenty of travelers to both Williamsburg and Chicago. Most visitors come to Williamsburg for the museums, the shopping scene, and the cuisine during these months. Also, the winter months attract visitors to Chicago because of the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

The weather in Chicago can be very cold. Williamsburg can be very cold during winter. In January, Williamsburg is generally much warmer than Chicago. Daily temperatures in Williamsburg average around 38°F (4°C), and Chicago fluctuates around 25°F (-4°C).

Williamsburg usually receives more sunshine than Chicago during winter. Williamsburg gets 168 hours of sunny skies, while Chicago receives 134 hours of full sun in the winter.

In January, Williamsburg usually receives more rain than Chicago. Williamsburg gets 3.6 inches (93 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.

Should I visit Williamsburg or Chicago in the Spring?

The spring brings many poeple to Williamsburg as well as Chicago. The spring months attract visitors to Williamsburg because of the natural beauty. Also, the beaches, the activities around the city, and the natural beauty are the main draw to Chicago this time of year.

Williamsburg is a little warmer than Chicago in the spring. The daily temperature in Williamsburg averages around 57°F (14°C) in April, and Chicago fluctuates around 52°F (11°C).

The sun comes out a lot this time of the year in Chicago. People are often attracted to the plentiful sunshine in Williamsburg this time of the year. In the spring, Williamsburg often gets more sunshine than Chicago. Williamsburg gets 253 hours of sunny skies this time of year, while Chicago receives 218 hours of full sun.

It's quite rainy in Chicago. Williamsburg usually gets less rain in April than Chicago. Williamsburg gets 3 inches (76 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year.

Typical Weather for Chicago and Williamsburg