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, it attracts visitors from all around. Other popular activities here include food, beaches, and shopping.

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 beaches, shopping, and museums.

Singapore and Chicago: Pros and Cons

Pros
  • Popular museums and historical sights
  • Good music scene
  • Nice resorts
  • Popular beach
  • Family-friendly
  • Good for couples and romance
  • Good for backpackers and budget travelers
  • Big city activities
  • Impressive beauty
Things to Consider
  • Less popular for nightlife
Pros
  • Popular museums and historical sights
  • Numerous theater shows
  • Active nightlife
  • Good music scene
  • Popular beach
  • Popular at Christmas
  • Known for Christmas markets
  • Family-friendly
  • Big city activities
  • Home to the Willis Tower (previously the Sears Tower)
Things to Consider
  • Less popular with couples
  • Less popular with backpackers


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, 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?

Singapore
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?

Singapore
Chicago

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?

Singapore
Chicago

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?

Singapore
Chicago

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?

Singapore
Chicago

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
Chicago

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
Chicago

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?

Singapore
Chicago

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?

Singapore
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 Better for Christmas?

Singapore
Chicago

Chicago is notable for its Christmas activities. However, Singapore 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.

Singapore does not offer Christmas activities.


Is Singapore or Chicago Better for Christmas Markets?

Singapore
Chicago

Chicago is a popular place for its Christmas markets. However, Singapore 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.

Singapore does not offer Christmas markets.

Is Singapore or Chicago Better for Families?

Singapore
Chicago

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
Chicago

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
Chicago

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
Chicago

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?

Singapore
Chicago

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
Chicago

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.


  • How many days in Singapore or Chicago? Ideal Length of Stay
    Singapore 2-7 
    Chicago 3-5

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 vibrant 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 Cultural Tours in Singapore, The Best Budget Tours to Singapore, The Best 2-Week Tours from Los Angeles, and The Best Family-Friendly Tours to United States of America.


Which place is cheaper, Chicago or Singapore?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Singapore is $152, while the average daily cost in Chicago is $288. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Singapore and Chicago in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Singapore $98
    Chicago $198
  • Accommodation Typical double-occupancy room
    Singapore $196
    Chicago $396
Compare Hotels in Singapore and Chicago

Looking for a hotel in Singapore or Chicago? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Singapore


Hotels in Chicago


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Singapore $10
    Chicago $37
Typical Local Transportation Prices in Singapore

Here are some examples of typical transportation prices from actual travelers in Singapore:


  • Taxi to Airport
    $24

Hired Cars and Shuttles in Singapore

Some specific examples of transportation prices in Singapore:

  • Changi International Airport Private MPV Transfer: $105
  • City Experience with National Orchid Garden + Roundtrip Transfers: $57
  • City Tour+Gardens by the Bay(FlowerDome&CloudForest)Transfers: $74
  • Departing Transfer to Changi Airport or Cruise Centre: $61
  • Downtown to Singapore Airport (SIN) - Departure Private Transfer: $36
  • ExhilaratingSentosa MorningTour(Guided Shared Roundtrip Transfer): $150
  • Glittering Singapore Night Out + Roundtrip Transfers: $80
  • MBCC & HFCC - Cruise Terminal to City Hotel Transfer: $29
  • Morning at the Zoo with Transfer : $65
  • Night Safari Tour with Transfer: $80
  • PRIVATE NIGHT TOUR: FOOD TASTINGS, RIVER CRUISE & TRANSFER: $214
  • Private Airport Transfer Service to or from Changi Airport SIN: $82

Typical Local Transportation Prices in Chicago

Here are some examples of typical transportation prices from actual travelers in Chicago:


  • Parking
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Chicago O´Hare International Airport Private Transfer One-Way: $27
  • Private Arrival Transfer from Chicago Airports ORD Or MDW: $50
  • Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer: $52
  • Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $53
  • Chicago to Chicago O'Hare Airport (ORD): Departure Transfer: $57
  • Chicago Midway Airport (MDW) to Chicago -Arrival Private Transfer: $58
  • Chicago to Chicago Airport (MDW) - Departure Private Transfer: $58
  • Private Transfer from Chicago Airport (ORD) - Chicago City: $58
  • Private Transfer from Chicago City to Chicago Airport (ORD): $58
  • Chicago to Chicago O'Hare Airport (ORD) - Departure Private Car Transfer: $63
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW): $90

Is it cheaper to fly into Singapore or Chicago?

Prices for flights to both Chicago and Singapore change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Singapore $27
    Chicago $49
Typical Food Prices in Singapore

Some typical examples of dining costs in Singapore are as follows:


  • Breakfast
    $4.50
  • Sugarcane Juice
    $1.48

Food Tours and Cooking Classes in Singapore

Also, here are some specific examples of food and dining related activities in Singapore.

  • Singapore : Traditional Snacks Cooking Class: $34
  • Secrets of Singapore Kick Scooter Tour with Dinner: $46
  • Secrets of Singapore Kick Scooter Tour with Dinner: $48
  • Chinatown Food Tour: The Preserving UNESCO Hawker Culture: $65
  • Guided Hawker Culture & Street Food Tour at Night: $65
  • Local Hawker Food Tour with Tastings: $65
  • Hawker Culture Food Tour and Sightseeing: $68
  • Marina Bay Sands Yacht Cruise with Dinner: $68
  • Eat Snap Katong Walking Food Tour: $72
  • Small Group: Michelin and Local Hawker Food Tour: $73
  • Private Korean Cooking Class in Balmoral Road: $74
  • Best Ever Katong Food Tour with Local Foodie - Eat till you drop!: $75

Typical Food Prices in Chicago

Below are a few samples from actual travelers for food and meal costs in Chicago:


  • Dinner for 1
    $24
  • Dinner for 3
    $118

Food Tours and Cooking Classes in Chicago

Also, here are some specific examples of food and dining related activities in Chicago.

  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class : $40
  • Fulton Market Delicious Donut Adventure and Walking Food Tour: $63
  • Chicago West Loop Pizza Crawl: $79
  • Friday Pizza Walk of Downtown Chicago: $79
  • Chicago Walking Food Tour With Secret Food Tours: $89
  • Chicago Buffet Dinner Cruise on Lake Michigan: $96
  • Saturday Chicago Pizza History and Tastings Bus Tour: $99
  • Chicago Half-Day Walking Food Tour with Free Bike or Kayak Rental: $99
  • Chicago Food Tour in Devon Ave: $125
  • Chicago Fireworks Dinner Cruise with Buffet: $129
  • Mother's Day Signature Dinner Cruise on Lake Michigan: $130
  • Chicago Gourmet Dinner Cruise on Lake Michigan: $132

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Singapore $32
    Chicago $47

Tours and Activities in Singapore

Some specific costs of activities, tours, and entrance tickets for Singapore are as follows:

  • Singapore Imaginary Experience: $2.57
  • The Civic District: A Self-Guided Audio Tour: $3.99
  • Kampong Glam: A Self-Guided Audio Tour: $4.99
  • The Civic District: Hear stories about Singapore's past on an audio tour: $5.20
  • Kampong Glam: A Self-Guided Audio Tour of Singapore's Malay Culture: $5.20
  • Singapore's History of Trade: A Self-Guided Audio Tour: $5.20
  • Big Little India: A Self-Guided Audio Tour: $5.20
  • Singapore Street Art Hunting in Kampong Glam: A Self-guided Audio Tour: $5.20
  • Indian Heritage Centre Admission Ticket: $5.36
  • Singapore Central Area: Quest Experience: $5.72
  • Indian Heritage Centre Entrance Ticket: $5.91
  • Sun Yat Sen Nanyang Memorial Hall Entry Ticket: $5.91

Typical Entertainment Prices in Chicago

Here are a few typical costs in Chicago for activities, ticket prices, and tours that come from previous visitors:


  • Sears Tower (family of 4)
    $102
  • Aquarium for 4
    $118
  • Water Taxi (family of 4)
    $22
  • IMAX Movie for Two
    $35
  • Shakespeare Play (2)
    $116
  • Art Institute (2)
    $36
  • U-Boat Tour (2)
    $8.00

Tours and Activities in Chicago

Here are a few actual costs in Chicago for available activities, ticket prices, and tours:

  • A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers: $5.40
  • Gangster Story Quest Experience in Chicago: $5.66
  • Chicago Lincoln Square Quest Experience: $5.72
  • Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
  • Chicago Self-Guided Audio Tour: $9.00
  • Chicago White Sox Baseball Game Ticket at Guaranteed Rate Field: $9.43
  • The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour: $12
  • Chicago Millennium Park Self-Guided Walking Tour: $15
  • Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt: $20
  • Chicago's Navy Pier Centennial Wheel Ticket: $21
  • The Chicago Theatre Tour Experience: $24

For more ideas for your next trip, check out The Best Free Things to Do in Chicago, Chicago Bucket List: The Best Places to See, and The Best Museums in Chicago.


Alcohol
  • Alcohol Drinks for one day
    Singapore $27
    Chicago $25

Sample the Local Flavors in Singapore

Here are a few nightlife and alcohol tours and activities from local tour providers in Singapore:

  • Party Singapore Bespoke Pub Crawl: $18
  • Tour of Tiger Brewery in Singapore: $21
  • Singapore Pub Crawl - Party like a Local: $26
  • Little India Pub Crawl: $26
  • Singapore Pub Crawl: $27
  • Halloween Horror Nightlife PartySingapore Bespoke Pub Crawl: $37
  • Brass Lion Gin Distillery Tour Ticket: $39
  • LeVeL33 Rooftop Brewery Tour & Craft Beer Tasting: $73

Sample the Local Flavors in Chicago

Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:

  • Chicago Walking Brewery Tour in Malt Row: $30
  • Walking tour to Chicago dive bars: $41
  • Milwaukee,Miller Brewery Tour&Tasting 1-Day Tour from Chicago: $93
  • Chicago Craft Brewery Barrel Bus Tour: $100


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.