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

Should you visit Singapore or Chicago?

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

Should I visit Singapore 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.

Singapore

Singapore is a glitzy, modern, and global city. Visitors will also find so much to do here because it's a large city with many sights and attractions. With stunning beauty, Singapore attracts visitors from all around. Other popular activities here include food, beaches, and shopping. See Singapore travel costs.

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. Chicago offers plenty of beauty for visitors. Other popular activities here include beaches, shopping, and museums. See Chicago travel costs.

Singapore and Chicago: Pros and Cons

Is there more to do in Singapore or Chicago?

Visitors will generally find more to do in Chicago than Singapore. While Singapore is larger than Chicago, Chicago has more sights, attractions, and activities for tourists. Chicago is very popular for its museums and attractions, theatre productions, nightlife, and christmas markets, while Singapore attracts visitors for its resorts, scuba diving & snorkeling, and impressive beauty. Singapore is famous for its blend of cultures, its lush gardens, and its clean streets. 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 Singapore different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is a must-visit destination for its sights and museums. Also, Singapore 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).

Many visitors head to Singapore specifically to visit some of its top-rated museums and other sights. The mix of cultures and unique history have led to museums and landmarks that mix historic and modern. The Merlion statue in Merlion Park has become a symbol of the city. For an educational experience, head to the Asian Civilizations Museum, and to see colonial architecture check out Fort Canning Park.

Is Singapore or Chicago Better for Theater?

Chicago is a must-visit destination for its shows and theatre. However, Singapore 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.

Singapore is not a theatre destination.

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

Both Singapore and Chicago offer a number of world-class restaurants to choose from.

For foodies, Singapore is an obvious choice, as it is one of the food capitals of the world. From local dives to five star restaurants, the city's food scene is all about diversity. Make sure you try Hainanese chicken rice, chili crab, and Hokkien prawn mee.

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.

Is Singapore or Chicago Better for Nightlife?

Chicago is a must-visit destination for its evening party scene. Also, Singapore is not as famous, but is still a good city to visit for nightlife.

Chicago is a world class 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.

With a handful of venues, visitors can find a fairly lively vibe in Singapore. It's all about the glitzy nightclubs and exclusive cocktail bars. Head to Clarke Quay, Marina Bay Sands, or one of the many rooftop bars to experience the best of Singapore's nightlife. Do keep in mind that the city has a high alcohol tax, and strict rules around drinking in public places during certain hours.

Is Singapore or Chicago Better for Music?

Both Singapore and Chicago offer world-class live music venues.

In Singapore you'll find nightly musicians performing at a variety of venues. As a globalized city, you'll find almost any type of music here. Popular music venues include Timbre, Zouk, and the Crazy Elephant.

Chicago is known as a music capital around the world. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Is Singapore or Chicago Better for Resorts?

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

If you're looking for a fantastic resort destination, Singapore is a perfect choice. From sleek high rises with rooftop pools to family-friendly resorts with kid oriented activities, this city has it all. Popular resorts include Oasia Resort Sentosa, Dusit Thani Laguna, and The Ritz-Carlton.

Chicago is not a resort destination.

Is Singapore or Chicago Better for Scuba Diving and Snorkeling?

Singapore is not so good for snorkeling and scuba diving. However, Chicago is not a scuba or snorkeling destination.

Singapore isn't the best spot for snorkeling. The best place to snorkel in the area is Pulau Hantu.

Chicago is not a scuba or snorkeling destination.

Is Singapore or Chicago Better for Beaches?

For a relaxing beach holiday, both Singapore and Chicago are nice choices.

Singapore is a good option for a beach vacation. You'll find most of the area's best beaches on Sentosa Island. There's a 2 kilometer long artificial beach that is split into Palawan Beach, Siloso Beach, and Tanjong Beach.

Many people head to Chicago to enjoy the beach. 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 Singapore or Chicago?

Both Singapore and Chicago are world-class shopping destinations.

Singapore is a world class destination for shoppers. You'll find tons of malls along Orchard Road, but for a more eclectic shopping experience head to the Chinatown Street Market.

People travel from around the world to go shopping in Chicago. 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.

Is Singapore or Chicago More Beautiful?

Singapore is a great destination for its scenery and beauty. Also, Chicago is still popular, but not quite as popular for its scenery and beauty.

With stunning beauty, Singapore attracts visitors from all around. It is a beautiful city with many lights and colorful neighborhoods.

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 Singapore or Chicago Better for Families?

Kids will enjoy a visit to either Singapore or Chicago.

As it has a large number of activities for kids, Singapore is a very family-friendly destination. With places like Sentosa and Universal Studios, there really is no shortage of activities for kids. There's also a zoo, an aquarium, and bird park, and many kid-friendly museums.

Chicago is one of the most popular family destinations. 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 Singapore or Chicago Better for Couples?

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

For those traveling as a couple, Singapore has plenty to offer. The city has stunning hotels, amazing restaurants, and plenty of fun activities that are perfect for couples.

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 Singapore or Chicago Better for Backpackers and Budget Travelers?

Singapore is renowned for backpackers. Also, Chicago is still popular, but not quite as popular for backpackers and budget travelers.

Singapore is a very popular city to visit for backpackers. Many backpackers use this city as a starting or ending point for their Southeast Asian backpacking trip. It's modern and glamourous, but still has plenty of backpacker-friendly and budget-friendly options.

It's common for backpackers to 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.

Is Singapore or Chicago Better for Students?

Singapore and Chicago are both world-class destinations for students and younger travelers.

Many students frequent Singapore. As such a diverse city, you'll find plenty of international students as well as expats to hang out with.

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.

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

Both Singapore and Chicago offer world-class public transit options.

Singapore has a world-class public transit network to take passengers everywhere in the city. There is the MRT subway system as well as buses that travel all over the city.

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.

Is Singapore or Chicago a more walkable city?

Singapore is renowned for its ease of walking around. Also, Chicago is still popular, but not quite as popular for its walkability.

Getting around Singapore on foot is easy. It's possible to walk in most areas in the city center. There are also park connectors that are nice for taking a stroll or going for a run.

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

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

Should I spend more time in Chicago or Singapore?

How long in Singapore or Chicago?

In either Singapore or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Singapore than Chicago because of the overall number of sights and activities. Usually, 2-7 days is a good amount of time for Singapore, and 3-5 days is enough time in Chicago.

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

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

One day in Singapore or Chicago?

Because Singapore is a large city, there are a variety of ways to spend your time. Travelers enjoy the resorts in the area as well. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

You'll find museums and theater around the city of Chicago. 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 Singapore or Chicago?

Because Singapore is a large city, there are a variety of ways to spend your time. The length of your trip often depends on your style of travel. A weekend here is typical. People often spend their time relaxing at one of the resorts. A weekend is a great amount of time to relax and see the many things that Singapore has to offer.

You'll find theater and nightlife around the edgey big city of Chicago. 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 Singapore or Chicago?

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

You'll find nightlife and live music around the cosmopolitan city of Chicago. 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 Singapore or Chicago?

It's hard to know how much time to spend in Singapore. Because Singapore is a large city, there are a variety of ways to spend your time. 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 Budget Tours to Singapore, The Best Tours for Seniors to Singapore, The Best 2-Week Tours from San Francisco, and The Best 2-Week Tours from Los Angeles.

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

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

Which is Bigger, Singapore or Chicago?

Singapore has a larger population, and is about 25% larger than the population of Chicago. When comparing the sizes of Singapore 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.