A Travel Price Comparison for United States of America Chicago vs. The Hamptons for Food, Nightlife, Families, and Couples

Should you visit Chicago or The Hamptons?

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 Chicago and The Hamptons can help you decide which place is right for you.

Chicago

Chicago is a multicultural, edgey, and cosmopolitan city. It's an amazing and huge city with tons of activities and things to do. Chicago is a gorgeous place to visit. It's also known for live music, food, and beaches. See Chicago travel costs.

The Hamptons

The Hamptons is a lavish, wealthy, and opulent beach destination. The Hamptons offers plenty of beauty for visitors. Other popular activities here include hiking, shopping, and nightlife. See The Hamptons travel costs.

Chicago and The Hamptons: Pros and Cons

Is there more to do in Chicago or The Hamptons?

Visitors will usually find more to do in Chicago than The Hamptons, as it offers more sights, attractions, and activities. Chicago is better known for its museums and attractions, theatre productions, food, nightlife, music, christmas markets, and big city activities, while The Hamptons is more popular for its resorts and hiking. Chicago is more touristy than The Hamptons and is known for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. Also, Chicago is famous for The Willis Tower (previously the Sears Tower). The Hamptons is well known for its long sandy beaches, charming seaside communities, opulent villas, and vacationing celebrities.

How is Chicago different from The Hamptons?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Chicago or The Hamptons?

Chicago is a world-class destination for its museums and landmarks. However, The Hamptons does not have museums and landmarks.

Visitors will find world class museums and historical sights in Chicago that are not to be missed. 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).

The Hamptons does not have museums and landmarks.

Is Chicago or The Hamptons Better for Theater?

Chicago is a world-class destination for theatre. However, The Hamptons is not a theatre destination.

Visitors will find world class theater shows, plays, and musicals in Chicago that are not to be missed. 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.

The Hamptons is not a theatre destination.

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

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

Many restaurants in Chicago have been singled out for their culinary prowess. 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 Hamptons has a delicious restaurant scene that relies on local flavors. There are a number of fine dining restaurants in the area and seafood is a favorite. Some restaurants are known to be frequented by vacationing celebrities, so if you're hoping to spot someone famous, do some research and you may have some luck.

Is Chicago or The Hamptons Better for Nightlife?

Chicago is a world-class destination for nightlife. Also, The Hamptons is still popular, but not quite as popular for nightlife and partying.

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.

If you're looking for night time activities The Hamptons has a few options to choose from. There are plenty of nightclubs and bars throughout the area. Head to East Hampton for some of the best options.

Is Chicago or The Hamptons Better for Music?

Chicago is a world-class destination for live music. However, The Hamptons is not a live music destination.

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

The Hamptons is not a live music destination.

Is Chicago or The Hamptons Better for Resorts?

The Hamptons is a great destination for its resorts. However, Chicago is not a resort destination.

Vacationers can choose from a number of terrific resorts in The Hamptons. Known as a hangout for the rich and famous, there is no shortage of luxury hotels and resorts in the area.

Chicago is not a resort destination.

Is Chicago or The Hamptons Better for Beaches?

Chicago and The Hamptons are notable choices for a beach vacation.

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.

The Hamptons has a beach worth visiting. The beaches in the area feature long stretches of soft sand and plenty of space to spread out. Many beaches do come with a hefty price tag though as they require you to pay for parking or a permit.

Is Chicago or The Hamptons Better for Hiking?

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

Many people include a hike when visiting The Hamptons. There are a number of picturesque walks through the dunes and wetlands around the area. There is plenty of peaceful nature to explore if you're looking for a break from city life.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or The Hamptons?

Shopping is a popular activity in both The Hamptons and Chicago.

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.

People travel from around the world to go shopping in The Hamptons. Known as a playground for the rich and famous, you can be assured there are plenty of shopping opportunities where you can flash your cash around town.

Is Chicago or The Hamptons More Beautiful?

You'll find a similar quality of notable scenery and beauty in both Chicago and The Hamptons.

Chicago offers plenty of beauty for visitors. The water makes this city a truly unique place to explore, and the world class architecture is not to be missed.

The Hamptons is a gorgeous place to visit. For a beautiful, upscale setting, this is a great destination near NYC.

Is Chicago or The Hamptons Better for Families?

Chicago is a world-class destination for its family-friendly activities. Also, The Hamptons is still popular, but not quite as popular for its kid-friendly activities.

Chicago is an extremely popular city to visit for families. 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.

The Hamptons offers lots of family activities. The area has a family-friendly setting with many outdoor activities and a children's museum. There are music events, children's parks, small zoos, and, of course, the beach. Also make sure you pick up some ice cream and enjoy that quintessential beach experience.

Is Chicago or The Hamptons Better for Couples?

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

Couples visit The Hamptons frequently as it offers plenty of romantic activities. Couples who enjoy beaches, dining out, and escaping the chaos of city life will enjoy a retreat here. The area has many beautiful parks and outdoor spaces, but there are also amazing restaurants that make for a great date night.

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 Chicago or The Hamptons Better for Backpackers and Budget Travelers?

Chicago is a city with good options for backpackers. However, The Hamptons is a beach destination with minimal options for backpackers and budget travelers.

Chicago is a good city 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.

The Hamptons is not the best destination for backpackers and budget travelers due to its high prices. It's more popular with the rich and famous than it is with the budget crowd, so you may struggle to find an affordable place to stay, much less a hostel.

Is Chicago or The Hamptons Better for Students?

Chicago is a world-class destination for students. However, The Hamptons is not popular with students.

Chicago is a very popular city 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.

The Hamptons is not popular with students.

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

Chicago is a world-class destination for its public transit. However, The Hamptons is a beach destination 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 quite limited in The Hamptons. While there are trains between towns, there aren't many options when it comes to public transit.

Is Chicago or The Hamptons a more walkable city?

Chicago is a great destination for its walkability. Also, The Hamptons is still popular, but not quite as popular for its high level of walkability.

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

The Hamptons is a somewhat walkable place. While some of the towns offer a nice place for a stroll, most of the Hamptons is not very walkable and it's best to have a car.

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

Should I spend more time in The Hamptons or Chicago?

How long in Chicago or The Hamptons?

Both Chicago and The Hamptons have a number of activities to choose from. With generally more activities and things to do, visitors tend to spend more time in The Hamptons than in Chicago. Usually, 3-5 days is a good amount of time for Chicago, and 3-7 days is enough time in The Hamptons.

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

Backpackers and budget travelers should spend more time in Chicago than The Hamptons 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 Chicago or The Hamptons?

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.

In The Hamptons, you'll find shopping and nightlife. Travelers enjoy the resorts in the area as well. One reason most visitors come is for the shopping. This beach destination offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Chicago or The Hamptons?

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.

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

Five days in Chicago or The Hamptons?

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.

The Hamptons 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 The Hamptons has to offer. Anyone can find something fun to do here.

A week in Chicago or The Hamptons?

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.

It's hard to know how much time to spend in The Hamptons. In The Hamptons, you'll find shopping and nightlife. One reason most visitors come is for the shopping. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.

For some great organized tour ideas, see The Best 2-Week Tours from San Francisco, The Best 2-Week Tours from Los Angeles, 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 Chicago and The Hamptons, we can see that Chicago is more expensive. And not only is The Hamptons much less expensive, but it is actually a significantly cheaper destination. So, traveling to The Hamptons would let you spend less money overall. Or, you could decide to spend more money in The Hamptons 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 The Hamptons.

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

Which is Bigger, Chicago or The Hamptons?

Chicago has a larger population, and is about 690 times larger than the population of The Hamptons. When comparing the sizes of Chicago and The Hamptons, 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 Chicago or The Hamptons?

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 Chicago or The Hamptons in the Summer?

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

In the summer, Chicago is around the same temperature as The Hamptons. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and The Hamptons averages at about 76°F (25°C).

It rains a lot this time of the year in The Hamptons. It's quite rainy in Chicago. In July, Chicago usually receives around the same amount of rain as The Hamptons. Chicago gets 3.9 inches (100 mm) of rain, while The Hamptons receives 4.1 inches (104 mm) of rain each month for the summer.

Should I visit Chicago or The Hamptons in the Autumn?

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

In October, Chicago is generally around the same temperature as The Hamptons. Daily temperatures in Chicago average around 56°F (14°C), and The Hamptons fluctuates around 58°F (14°C).

Chicago usually gets less rain in October than The Hamptons. Chicago gets 2.2 inches (56 mm) of rain, while The Hamptons receives 3 inches (77 mm) of rain this time of the year.

Should I visit Chicago or The Hamptons in the Winter?

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

The weather in The Hamptons can be very cold. Chicago can be very cold during winter. Chicago is much colder than The Hamptons in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and The Hamptons fluctuates around 31°F (-0°C).

In January, Chicago usually receives less rain than The Hamptons. Chicago gets 1.9 inches (47 mm) of rain, while The Hamptons receives 3.2 inches (81 mm) of rain each month for the winter.

Should I visit Chicago or The Hamptons in the Spring?

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

In the spring, Chicago is around the same temperature as The Hamptons. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and The Hamptons averages at about 51°F (11°C).

Chicago receives a lot of rain in the spring. Chicago usually gets more rain in April than The Hamptons. Chicago gets 4.3 inches (108 mm) of rain, while The Hamptons receives 3.8 inches (96 mm) of rain this time of the year.

Typical Weather for The Hamptons and Chicago