A Travel Price Comparison for United States of America Hilton Head Island vs. Chicago for Food, Families, Beaches, and Couples

Should you visit Hilton Head Island or Chicago?

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

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Hilton Head Island and Chicago can help you decide which place is right for you.

Hilton Head Island

Hilton Head Island is a peaceful, beautiful, and resort-filled coastal town. It offers plenty of beauty for visitors. Other popular activities here include shopping, food, and beaches.

Chicago

Chicago is a diverse, vibrant, and multicultural 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. It's also popular because of the shopping, museums, and theater.

Hilton Head Island and Chicago: Pros and Cons

Is there more to do in Hilton Head Island or Chicago?

Travelers will usually find more to do in Chicago. Although Hilton Head Island and Chicago are popular destinations, Chicago has more sights and attractions for tourists. Chicago is very popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Hilton Head Island attracts visitors for its resorts and beaches. Hilton Head Island is famous for its long sandy beaches, many golf courses, popular tennis camps, and accessible bike trails. 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 Hilton Head Island different from Chicago?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Hilton Head Island or Chicago?

Chicago is terrific for its museums and history. However, Hilton Head Island does not have museums and landmarks.

With plenty of landmarks, attractions, and museums, Chicago has many famous sights for visitors. 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).

Hilton Head Island does not have museums and landmarks.

Is Hilton Head Island or Chicago Better for Theater?

Chicago is terrific for its shows and theatre. However, Hilton Head Island is not a theatre destination.

The theater scene in Chicago is world-class. 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.

Hilton Head Island is not a theatre destination.

Is the Food Better in Hilton Head Island or Chicago? Which Destination has the Best Restaurants?

Chicago is terrific for its restaurants. Also, Hilton Head Island is not quite as popular, but is fairly good for its restaurant scene.

Chicago has long been recognized as a culinary destination with great restaurants. 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.

Hilton Head Island offers number of good local restaurants to choose from. The island has many famous restaurants but reservations during the summer are a must. Restaurants can get very crowded during peak times. For some of the best restaurants head to Shelter Cove or Harbour Town. Popular local dishes include fried seafood and oysters.

Is Hilton Head Island or Chicago Better for Nightlife?

Chicago is terrific for its evening party scene. However, Hilton Head Island is lacking in good options for nightlife.

Chicago is a must-see party destination. 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.

Things get quiet in the evenings in Hilton Head Island. There are a few sports bars and comedy clubs, but nightlife isn't really a thing in Hilton Head. This is very much a family destination that shuts down with the sunset.

Is Hilton Head Island or Chicago Better for Music?

Chicago is terrific for its music scene. However, Hilton Head Island is not a live music destination.

Chicago has become a mecca for musicians from around the world. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Hilton Head Island is not a live music destination.

Is Hilton Head Island or Chicago Better for Resorts?

Hilton Head Island is a great destination for its resorts. However, Chicago is not a resort destination.

Vacationers can choose from a number of terrific resorts in Hilton Head Island. Most of the accommodation in the area is in the form of weekly condo rentals, which usually include a pool and outdoor space. Tennis and golf are also popular on the island so many resorts have facilities for each.

Chicago is not a resort destination.

Is Hilton Head Island or Chicago Better for Beaches?

Hilton Head Island is a great destination for the beach. Also, Chicago is still popular, but not quite as popular for its beaches.

Hilton Head Island is a very popular place to visit for its beaches. The island has nice beaches that are popular with families. They are great for swimming during the spring, summer, and fall seasons. While some beaches may get a bit crowded during peak holidays, they're usually pretty relaxed and less crowded than many nearby beaches.

Chicago has a beach worth visiting. 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.

Is the Shopping Better in Hilton Head Island or Chicago?

Chicago is terrific for its shopping areas. Also, Hilton Head Island is not quite as popular, but is fairly good for shopping.

Many people travel to Chicago specifically to go shopping. 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.

Hilton Head Island is a great destination for shopping. The area has upscale shopping with designer names and local venues. Popular shopping areas include Shelter Cove Town Center and Harbor Town.

Is Hilton Head Island or Chicago Better for Christmas?

Chicago is a very popular place for its Christmas holiday experiences. However, Hilton Head Island does not offer Christmas activities.

Since it has plenty to do, Chicago is a very popular place to visit during Christmas. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Hilton Head Island does not offer Christmas activities.

Is Hilton Head Island or Chicago Better for Christmas Markets?

Chicago is very good for visiting Christmas markets. However, Hilton Head Island does not offer Christmas markets.

Chicago offers some nice Christmas markets. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Hilton Head Island does not offer Christmas markets.

Is Hilton Head Island or Chicago Better for Families?

You'll find fantastic kid-friendly activities in either Hilton Head Island or Chicago.

Hilton Head Island is one of the most popular family destinations. This area is a popular family-friendly beach destination with a number of summer events for the whole family, peaceful beaches, and family-friendly restaurants throughout. Older kids will enjoy cycling around the island's many bike trails or attending a popular tennis camp.

Chicago is an amazing family-friendly coastal town to visit. 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 Hilton Head Island or Chicago Better for Couples?

Both Hilton Head Island and Chicago are nice destinations to visit as a couple.

Hilton Head Island is a good coastal town for couples to visit. While the area is most popular with families, it is a fun place to explore as a couple because of the many high end restaurants and the beautiful setting. Couples can rent bikes to explore or play a friendly game of tennis.

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 Hilton Head Island or Chicago Better for Backpackers and Budget Travelers?

Chicago is very good for backpackers and budget travelers. However, Hilton Head Island is not a backpacker-friendly destination.

Chicago is popular with backpackers and budget travelers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Hilton Head Island is not a backpacker-friendly destination.

Is Hilton Head Island or Chicago Better for Students?

Chicago is terrific for its student-friendly activities. However, Hilton Head Island is not popular with students.

Students come from all over the world to visit 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.

Hilton Head Island is not popular with students.

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

Chicago is terrific for times when you don't have a car. However, Hilton Head Island is lacking in good options for its public transit.

The thorough and effecient public transit system of Chicago can take you anywhere. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is limited or non-existant in Hilton Head Island. You must have a car to get most places on the island, unless you bike. Rush hour during summer months can have intense traffic.

Is Hilton Head Island or Chicago a more walkable city?

Chicago is a very popular place for its ease of walking around. However, Hilton Head Island is lacking in good options for its walkability.

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

Hilton Head Island is generally not very walkable. You really need a car to get around, but for those who are motivated, there is a great network of bike trails. It's mostly used for recreational purposes though.

For even more information, also check out Is Hilton Head Island Worth Visiting? and Is Chicago Worth Visiting?.

Should I spend more time in Chicago or Hilton Head Island?

How long in Hilton Head Island or Chicago?

In either Hilton Head Island or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Hilton Head Island than Chicago because of the overall number of sights and activities. Usually, 5-7 days is a good amount of time for Hilton Head Island, and 3-5 days is enough time in Chicago.

Families should spend more time in Chicago than Hilton Head Island. 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 Hilton Head Island. 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 Hilton Head Island 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 Hilton Head Island or Chicago?

In Hilton Head Island, you'll find food and shopping. Travelers enjoy the resorts in the area as well. This coastal town offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

Chicago is a multicultural big city where you can fill many days. This city offers something for everyone. But since there are so many activities, you'll likely want to spend more than one day exploring.

A weekend in Hilton Head Island or Chicago?

In Hilton Head Island, you'll find shopping and food. The length of your trip often depends on your style of travel. Most people come for the beaches. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Chicago is a popular place to visit. Chicago is a multicultural city where you can fill many days. With so much to do, a weekend is probably not enough time to see everything.

Five days in Hilton Head Island or Chicago?

Hilton Head Island is a great place to explore. It is common to spend five days here. You can also relax and pamper yourself at one of the resorts. Five days is a great amount of time to relax and see the many things that Hilton Head Island has to offer. Anyone can find something fun to do here.

Chicago is a big city destination where you can fill many days. This is a popular place to visit for five days. Anyone can find something fun to do here. Five days is a great amount of time to relax and see the many things that Chicago has to offer.

A week in Hilton Head Island or Chicago?

It's hard to know how much time to spend in Hilton Head Island. In Hilton Head Island, you'll find shopping and food. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.

Chicago is a popular place that is full of things to see and experience. It offers something for everyone. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Anchorage, The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, and The Best 2-Week Tours from New York City.

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

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

Which is Bigger, Hilton Head Island or Chicago?

Chicago has a larger population, and is about 80 times larger than the population of Hilton Head Island. When comparing the sizes of Hilton Head Island 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 Hilton Head Island or Chicago?

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 Hilton Head Island or Chicago in the Summer?

Both Chicago and Hilton Head Island during the summer are popular places to visit. The summer months attract visitors to Hilton Head Island because of the beaches and the family-friendly experiences. Furthermore, the beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Chicago this time of year.

Hilton Head Island is a little warmer than Chicago in the summer. The daily temperature in Hilton Head Island averages around 82°F (28°C) in July, and Chicago fluctuates around 77°F (25°C).

In Chicago, it's very sunny this time of the year. It's quite sunny in Hilton Head Island. In the summer, Hilton Head Island often gets less sunshine than Chicago. Hilton Head Island gets 267 hours of sunny skies this time of year, while Chicago receives 326 hours of full sun.

Chicago gets a good bit of rain this time of year. It rains a lot this time of the year in Hilton Head Island. Hilton Head Island usually gets more rain in July than Chicago. Hilton Head Island gets 7.9 inches (200 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.

Should I visit Hilton Head Island or Chicago in the Autumn?

The autumn attracts plenty of travelers to both Hilton Head Island and Chicago. The shopping scene and the natural beauty of the area are the main draw to Hilton Head Island this time of year. Furthermore, many travelers come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In the autumn, Hilton Head Island is a little warmer than Chicago. Typically, the autumn temperatures in Hilton Head Island in October average around 68°F (20°C), and Chicago averages at about 56°F (14°C).

In Hilton Head Island, it's very sunny this time of the year. Hilton Head Island usually receives more sunshine than Chicago during autumn. Hilton Head Island gets 223 hours of sunny skies, while Chicago receives 195 hours of full sun in the autumn.

In October, Hilton Head Island usually receives more rain than Chicago. Hilton Head Island gets 2.8 inches (71 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.

Should I visit Hilton Head Island or Chicago in the Winter?

The winter brings many poeple to Hilton Head Island as well as Chicago. Many travelers come to Hilton Head Island for the shopping scene and the cuisine. Additionally, many visitors come to Chicago in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Chicago can get quite cold in the winter. In January, Hilton Head Island is generally much warmer than Chicago. Daily temperatures in Hilton Head Island average around 48°F (9°C), and Chicago fluctuates around 25°F (-4°C).

In the winter, Hilton Head Island often gets more sunshine than Chicago. Hilton Head Island gets 176 hours of sunny skies this time of year, while Chicago receives 134 hours of full sun.

Hilton Head Island usually gets more rain in January than Chicago. Hilton Head Island gets 2.9 inches (74 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.

Should I visit Hilton Head Island or Chicago in the Spring?

Both Chicago and Hilton Head Island are popular destinations to visit in the spring with plenty of activities. Many visitors come to Hilton Head Island in the spring for the beaches and the natural beauty. Also, most visitors come to Chicago for the beaches, the activities around the city, and the natural beauty during these months.

Hilton Head Island is much warmer than Chicago in the spring. The daily temperature in Hilton Head Island averages around 67°F (19°C) in April, and Chicago fluctuates around 52°F (11°C).

It's quite sunny in Chicago. The sun comes out a lot this time of the year in Hilton Head Island. Hilton Head Island usually receives more sunshine than Chicago during spring. Hilton Head Island gets 275 hours of sunny skies, while Chicago receives 218 hours of full sun in the spring.

It rains a lot this time of the year in Chicago. In April, Hilton Head Island usually receives less rain than Chicago. Hilton Head Island gets 2.9 inches (74 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.

Typical Weather for Chicago and Hilton Head Island