A Travel Price Comparison for Families, Couples, and Backpackers Santorini vs. Chicago for Attractions, Food, Nightlife, and Families

Should you visit Santorini or Chicago?

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

If you're trying to decide where to visit between Santorini or Chicago, this travel comparison, which includes costs, can help. The overall cost of travel is usually a consideration when deciding where to go next, and the cost comparison down below can help you decide based on the average prices from other travelers along with your own travel budget.

Santorini

Santorini is a romantic, stunning, and historic island. The famous beauty of this place is one of the main draws. With a quaint atmosphere, it also offers a unique feeling. Other popular activities here include shopping, museums, and nightlife.

Chicago

Chicago is a vibrant, multicultural, and edgey city. With plenty of activities and things to do, it's a huge city that draws plenty of visitors. It's a beautiful place to visit, too. Visitors also love the food, beaches, and shopping.

Santorini and Chicago: Pros and Cons

Is there more to do in Santorini or Chicago?

Travelers will usually find more to do in Chicago than Santorini, as it is bigger with more sights, attractions, and activities for visitors. Chicago is more popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Santorini is known for its resorts, scuba diving & snorkeling, hiking, impressive beauty, and quaint atmosphere. Santorini is more touristy than Chicago and is popular for its beautiful volcanic beaches, stunning natural beauty, and breathtaking sunsets over the whitewashed villages. Chicago is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also home to The Willis Tower (previously the Sears Tower).

How is Santorini different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is an unbeatable place for its historical sights. Also, Santorini is not as popular, but is still a nice island for its sights and museums.

The museums and tourist attractions in Chicago are world-renowned. 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).

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Santorini. One of the most impressive historical sights is Akrotiri Archaeological Site. The island has many archeological sites as well as the Archeological Museum in Fira.

Is Santorini or Chicago Better for Theater?

Chicago is an unbeatable place for its theatre productions. However, Santorini is not a theatre destination.

Famous for its theaters and plays, you'll find world-renowned shows in Chicago. 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.

Santorini is not a theatre destination.

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

Chicago is an unbeatable place for its local flavors and cuisine. Also, Santorini is not as popular, but is still a nice island for its local cuisine and restaurants.

Known for it's food and restaurant scene, Chicago is always at the top of any foodie's travel list. 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 many up and coming restaurants in the Santorini area. Popular foods on this island include fava, Greek salad, and kofta.

Is Santorini or Chicago Better for Nightlife?

Chicago is an unbeatable place for nightlife and partying. Also, Santorini is not as popular, but is still a nice island for its evening party scene.

The nightlife in Chicago is well established with world renowned clubs and venues. 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.

There's a variety of activities in the evening in Santorini. It is one of the calmer, more romantic islands in Greece. For the best nightlife, you'll want to stay near Fira.

Is Santorini or Chicago Better for Music?

Chicago is an unbeatable place for its live music scene. However, Santorini is not a live music destination.

With so many music venues, you're guaranteed a show any night of the week in Chicago. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Santorini is not a live music destination.

Is Santorini or Chicago Better for Resorts?

Santorini is renowned for its resorts. However, Chicago is not a resort destination.

If you're looking for a fantastic resort destination, Santorini is a perfect choice. The resorts range from all-inclusive options to resorts with a more local feel. The island is one of the most romantic of the Greek Islands, and the resorts are no exception.

Chicago is not a resort destination.

Is Santorini or Chicago Better for Scuba Diving and Snorkeling?

Santorini is very good for snorkeling and scuba diving. However, Chicago is not a scuba or snorkeling destination.

It's worth going snorkeling or scuba diving in Santorini. Some of the best snorkeling places are found at Red Beach, White Beach, and the less accessible Kambia. One of the island's best diving spots is Caldera Beach.

Chicago is not a scuba or snorkeling destination.

Is Santorini or Chicago Better for Beaches?

Both Santorini and Chicago have good beaches worth visiting.

Santorini has a beach worth visiting. The island has many beaches, most of which are made of black pebbly sand that are a result of the island's volcanic history. Popular beaches include Perissa Beach, Kamari Beach, and Perivolos Beach.

Plenty of visitors enjoy relaxing on the beach in Chicago. 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 Santorini or Chicago Better for Hiking?

Santorini is very good for its hiking experiences. However, Chicago is not a hiking destination.

Many people include a hike when visiting Santorini. The best hiking trails on the island pass by quaint villages and offers stunning ocean views. You can also hike along the edge of a volcano.

Chicago is not a hiking destination.

Is the Shopping Better in Santorini or Chicago?

Chicago is an unbeatable place for its shopping opportunities. Also, Santorini is not as popular, but is still a nice island for its shopping areas.

Known for shopping, Chicago draws large crowds to its stores. 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.

Browsing through shops is a popular activity in Santorini. Towns around the island are filled with clothing and jewelry boutiques as well as many unique Greek shopping experiences.

Is Santorini or Chicago Better for Christmas?

Chicago is a great city for its Christmas holiday experiences. However, Santorini does not offer Christmas activities.

Chicago is a very popular destination during Christmas. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Santorini does not offer Christmas activities.

Is Santorini or Chicago Better for Christmas Markets?

Chicago is a nice place to visit for visiting Christmas markets. However, Santorini does not offer Christmas markets.

Chicago has Christmas markets worth visiting. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Santorini does not offer Christmas markets.

Is Santorini or Chicago Better for Families?

Chicago is an unbeatable place for its kid-friendly activities. Also, Santorini is not as popular, but is still a nice island for its family-friendly activities.

Chicago is an amazing family-friendly city 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.

Santorini is a family-friendly place to visit. It is a calmer destination than many of the Greek Islands. While it's a great place to relax with kids, the beaches aren't as good as they are on some of the other islands. Most families hang out in Kamari and Perissa Beach.

Is Santorini or Chicago Better for Couples?

Santorini is renowned for couples. Also, Chicago is still popular, but not quite as popular for romance.

For those traveling as a couple, Santorini has plenty to offer. It is a dream honeymoon destination that is famous for its picturesque setting and luxury resorts. For many couples, this is a top pick for a romantic trip to the Greek Isles.

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 Santorini or Chicago Better for Backpackers and Budget Travelers?

For backpackers, both Santorini and Chicago are good places to visit.

It's common for backpackers to visit Santorini. The island has its share of 5 star resorts, but if you head a few streets in you'll find some surprisingly affordable accommodation. Backpackers are welcomed on the island and beaches are free, so it's possible to get by on a relatively low budget.

Chicago is a good island to visit for backpackers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Is Santorini or Chicago Better for Students?

Chicago is an unbeatable place for its student-friendly activities. However, Santorini is not popular with students.

Chicago is a great destination for students. 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.

Santorini is not popular with students.

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

Chicago is an unbeatable place for times when you don't have a car. Also, Santorini is not as popular, but is still a nice island for its public transit.

Visitors in Chicago can get around quickly with the extensive public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Santorini has a few public transit options. There is a bus system, KTEL Santorini Buses, that runs 23 buses during the summer months but only a small fraction of that operate during the winter months.

Is Santorini or Chicago a more walkable city?

Chicago is a great city for its high level of walkability. Also, Santorini is not as popular, but is still a nice island for its ease of walking around.

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

Santorini is a somewhat walkable island. Many towns on the island are walkable, including Fira, but the actual island is too large to explore on foot.

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

Should I spend more time in Chicago or Santorini?

How long in Santorini or Chicago?

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

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

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

People visit Chicago because there is so much to do. Since there is so much to do in the area, one day is probably not enough for all of it. It has many unique tourist attractions and fascinating things to do.

A weekend in Santorini or Chicago?

In Santorini, you'll find museums and nightlife. The length of your trip often depends on your style of travel. People often spend their time relaxing at one of the resorts. Since there is so much to do in the area, a weekend is probably not enough for all of it.

People visit Chicago because there is so much to do. A weekend is usually not enough time for a trip here as there is plenty to do. This city offers a variety of activities to choose from.

Five days in Santorini or Chicago?

Santorini 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 Santorini has to offer. Anyone can find something fun to do here.

People visit Chicago because there is so much to do. The length of your ideal trip is an individual decision. If you have five days, this city makes for a great vacation. Five days should give you a good understanding of everything this city has to offer.

A week in Santorini or Chicago?

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

Chicago 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.

For some great organized tour ideas, see The Best Luxury Tours to Greece, The Best Budget Tours to Greece, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.

When we compare the travel costs of actual travelers between Santorini and Chicago, we can see that Chicago is more expensive. And not only is Santorini much less expensive, but it is actually a significantly cheaper destination. Since Santorini is in Europe and Chicago is in North America, this is one of the main reasons why the costs are so different, as different regions of the world tend to have overall different travel costs. So, traveling to Santorini would let you spend less money overall. Or, you could decide to spend more money in Santorini 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 Santorini.

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

Which is Bigger, Santorini or Chicago?

Chicago has a larger population, and is about 5 times larger than the population of Santorini. When comparing the sizes of Santorini 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.