A Travel Price Comparison for United States of America Chicago vs. Kennebunkport for Attractions, Food, Nightlife, and Families

Should you visit Chicago or Kennebunkport?

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 Kennebunkport can help you decide which place is right for you.

Chicago

Chicago is a cosmopolitan, diverse, and vibrant city. It's an amazing and huge city with tons of activities and things to do. It's a gorgeous place to visit. Other reasons to visit include nightlife, live music, and food.

Kennebunkport

Kennebunkport is a character-filled, charming, and quaint town. As this is a charming small town, visitors also come to explore the sights and local activities. It offers plenty of beauty for visitors. Other popular activities here include shopping, museums, and nightlife.

Chicago and Kennebunkport: Pros and Cons

Is there more to do in Chicago or Kennebunkport?

Visitors will usually find more to do in Chicago than Kennebunkport, as it offers more sights, attractions, and activities. Chicago is better known for its museums, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, and big city activities, while Kennebunkport is more popular for its resorts, hiking, and small town charm. Chicago is well 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). Kennebunkport is well known for its historic and charming atmosphere, its wonderful local seafood, and its stunning coastline.

How is Chicago different from Kennebunkport?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Kennebunkport 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 Kennebunkport?

Chicago is very popular for its historical sights. Also, Kennebunkport is not as popular, but is still a nice town for its sights and museums.

Travelers visit Chicago from around the world to see its many world-famous attractions. 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).

Kennebunkport offers a variety of museums and landmarks to choose from. There are a handful of local museums around town like the Brick Store Museum, the First Families Kennebunkport Museum, and the Seashore Trolley Museum.

Is Chicago or Kennebunkport Better for Theater?

Chicago is very popular for theatre. However, Kennebunkport 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.

Kennebunkport is not a theatre destination.

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

Chicago is very popular for its local flavors and cuisine. Also, Kennebunkport is not as popular, but is still a nice town for its local cuisine and restaurants.

For foodies, Chicago is an obvious choice, as it is one of the food capitals of the world. 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.

Eating is part of the travel experience when you visit Kennebunkport. Fine dining, seafood restaurants, and local cafes all make this a wonderful town for foodies. The town's famous for its lobster, but you can also try the scallops, crab, or oysters.

Is Chicago or Kennebunkport Better for Nightlife?

Chicago is very popular for nightlife. Also, Kennebunkport is not as popular, but is still a nice town for nightlife and partying.

Chicago is a party destination, and you'll find plenty of activity all night long. 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 Kennebunkport. You can check out the happy hours that many of the bars in the waterfront area host regularly.

Is Chicago or Kennebunkport Better for Music?

Chicago is very popular for live music. However, Kennebunkport is not a live music destination.

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.

Kennebunkport is not a live music destination.

Is Chicago or Kennebunkport Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Kennebunkport. Luxury resorts and classic inns provide traditional and local accommodation options for visitors.

Chicago is not a resort destination.

Is Chicago or Kennebunkport Better for Beaches?

Chicago is a popular place for its beaches. However, Kennebunkport is not a beach destination.

Chicago is a good option for a beach vacation. 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.

Kennebunkport is not a beach destination. It's lined with rocky and sandy coastlines that are perfect for finding critters at low tide or searching for seashells. Mother's Beach is popular with families and Gooch's Beach is a popular place for walking. Middle Beach is a great spot for climbing over rocks.

Is Chicago or Kennebunkport Better for Hiking?

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

Many people include a hike when visiting Kennebunkport. There are waterfront walks and coastal trails. There are also trails that wander through forests or past marshland.

Chicago is not a hiking destination.

Is the Shopping Better in Chicago or Kennebunkport?

Chicago is very popular for shopping. Also, Kennebunkport is not as popular, but is still a nice town for its shopping opportunities.

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.

Kennebunkport is a popular shopping destination with plenty of stores. Head to Dock's Square for the best local shops with a charming atmosphere.

Is Chicago or Kennebunkport Better for Christmas?

Chicago is great for its Christmas holiday experiences. However, Kennebunkport 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.

Kennebunkport does not offer Christmas activities.

Is Chicago or Kennebunkport Better for Christmas Markets?

Chicago is a popular place for visiting Christmas markets. However, Kennebunkport 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.

Kennebunkport does not offer Christmas markets.

Is Chicago or Kennebunkport Better for Families?

Chicago is very popular for its kid-friendly activities. Also, Kennebunkport is not as popular, but is still a nice town for its family-friendly activities.

As it has a large number of activities for kids, Chicago is a very family-friendly destination. 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.

Kennebunkport is a very kid-friendly city. You can explore the rocks around Mother's Beach or take the kids out on a lobster boat. There's also a lot of history around Dock's Square and plenty of kid-friendly restaurants in town.

Is Chicago or Kennebunkport Better for Couples?

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

Couples visit Kennebunkport frequently as it offers plenty of romantic activities. Beaches, romantic hotels, and charming local restaurants make this a perfect couple's destination.

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 Kennebunkport Better for Backpackers and Budget Travelers?

Chicago is a popular place for backpackers and budget travelers. However, Kennebunkport is not a good destination for backpackers.

Plenty of budget travelers 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.

Kennebunkport is a challenging destination for budget travelers and backpackers due to the higher prices. You'll find cabins and motels in the area, but no real hostels.

Is Chicago or Kennebunkport Better for Students?

Chicago is very popular for its student-friendly activities. However, Kennebunkport is not popular with students.

Many students frequent 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.

Kennebunkport is not popular with students.

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

Chicago is very popular for times when you don't have a car. However, Kennebunkport is not a good destination for its public transit.

Chicago has an effecient and thorough public transportation system which can take you anywhere in the city. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is generally limited in Kennebunkport. During the summer months there's a Shoreline Trolley that connects towns.

Is Chicago or Kennebunkport a more walkable city?

Chicago is great for its walkability. Also, Kennebunkport is not as popular, but is still a nice town for its high level of walkability.

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

Kennebunkport is a somewhat walkable place. It's downtown is compact and particularly walkable.

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

Should I spend more time in Kennebunkport or Chicago?

How long in Chicago or Kennebunkport?

It's fun to spend time in either Chicago or Kennebunkport. Generally, people tend to spend more time in Chicago due to the larger number of activities and things to do. Usually, 3-5 days is a good amount of time for Chicago, and 2-4 days is enough time in Kennebunkport.

Families should spend more time in Chicago than Kennebunkport. 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 Kennebunkport. 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 Kennebunkport 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 Kennebunkport?

Chicago is a bustling city that offers something for everyone. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.

Kennebunkport is a small town with plenty to do. Travelers enjoy the resorts in the area as well. This town 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 Kennebunkport?

It's hard to know how much time to spend in Chicago. It has many unique tourist attractions and fascinating things to do. A weekend is usually not enough time for a trip here as there is plenty to do.

Kennebunkport might be a small town, but there's plenty to do in the area. 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 Kennebunkport has to offer.

Five days in Chicago or Kennebunkport?

Chicago is a bustling city that offers something for everyone. This city offers a variety of activities to choose from. If you have five days, this is a great place to go. Five days is usually enough time to experience most activities.

Kennebunkport is a great place to explore. You can also relax and pamper yourself at one of the resorts. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

A week in Chicago or Kennebunkport?

You'll find theater and nightlife around the city of Chicago. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.

It's hard to know how much time to spend in Kennebunkport. Since Kennebunkport is a small town, it's easily explored when your time is limited. It's also a relaxing resort destination. One week may feel like too much time unless you plan to do a lot of relaxing.

For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, and The Best Historical Tours in United States of America.

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

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

Which is Bigger, Chicago or Kennebunkport?

Chicago has a larger population, and is about 1820 times larger than the population of Kennebunkport. When comparing the sizes of Chicago and Kennebunkport, 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 Kennebunkport?

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 Chicago or Kennebunkport in the Summer?

Both Kennebunkport and Chicago during the summer are popular places to visit. Most visitors come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences during these months. Furthermore, the summer months attract visitors to Kennebunkport because of the hiking, the small town charm, and the family-friendly experiences.

In the summer, Chicago is a little warmer than Kennebunkport. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and Kennebunkport averages at about 69°F (20°C).

In Kennebunkport, it's very sunny this time of the year. It's quite sunny in Chicago. In the summer, Chicago often gets more sunshine than Kennebunkport. Chicago gets 326 hours of sunny skies this time of year, while Kennebunkport receives 282 hours of full sun.

It rains a lot this time of the year in Chicago. Chicago usually gets more rain in July than Kennebunkport. Chicago gets 3.9 inches (100 mm) of rain, while Kennebunkport receives 2.6 inches (66 mm) of rain this time of the year.

Should I visit Chicago or Kennebunkport in the Autumn?

The autumn attracts plenty of travelers to both Chicago and Kennebunkport. The autumn months attract visitors to Chicago because of the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area. Furthermore, the hiking trails, the shopping scene, the small town atmosphere, and the natural beauty of the area are the main draw to Kennebunkport this time of year.

In October, Chicago is generally a little warmer than Kennebunkport. Daily temperatures in Chicago average around 56°F (14°C), and Kennebunkport fluctuates around 49°F (9°C).

Chicago usually receives around the same amount of sunshine as Kennebunkport during autumn. Chicago gets 195 hours of sunny skies, while Kennebunkport receives 196 hours of full sun in the autumn.

In October, Chicago usually receives less rain than Kennebunkport. Chicago gets 2.2 inches (56 mm) of rain, while Kennebunkport receives 3.3 inches (84 mm) of rain each month for the autumn.

Should I visit Chicago or Kennebunkport in the Winter?

The winter brings many poeple to Chicago as well as Kennebunkport. The museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Chicago this time of year. Additionally, many travelers come to Kennebunkport for the museums, the shopping scene, and the cuisine.

Be prepared for some very cold days in Kennebunkport. It's quite cold in Chicago in the winter. Chicago is a little warmer than Kennebunkport in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and Kennebunkport fluctuates around 21°F (-6°C).

In the winter, Chicago often gets less sunshine than Kennebunkport. Chicago gets 134 hours of sunny skies this time of year, while Kennebunkport receives 163 hours of full sun.

Chicago usually gets less rain in January than Kennebunkport. Chicago gets 1.9 inches (47 mm) of rain, while Kennebunkport receives 3.4 inches (86 mm) of rain this time of the year.

Should I visit Chicago or Kennebunkport in the Spring?

Both Kennebunkport and Chicago are popular destinations to visit in the spring with plenty of activities. Many travelers come to Chicago for the beaches, the activities around the city, and the natural beauty. Also, many visitors come to Kennebunkport in the spring for the small town charm and the natural beauty.

In the spring, Chicago is much warmer than Kennebunkport. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and Kennebunkport averages at about 43°F (6°C).

It's quite sunny in Kennebunkport. The sun comes out a lot this time of the year in Chicago. Chicago usually receives around the same amount of sunshine as Kennebunkport during spring. Chicago gets 218 hours of sunny skies, while Kennebunkport receives 212 hours of full sun in the spring.

It's quite rainy in Chicago. In April, Chicago usually receives more rain than Kennebunkport. Chicago gets 4.3 inches (108 mm) of rain, while Kennebunkport receives 3.3 inches (85 mm) of rain each month for the spring.

Typical Weather for Kennebunkport and Chicago