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

Should you visit Islamorada or Chicago?

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

If you're trying to decide where to visit between Islamorada 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.

Islamorada

Islamorada is a tropical, adventurous, and relaxing village. With stunning beauty, it attracts visitors from all around. Other popular activities here include scuba diving and snorkeling, beaches, and shopping.

Chicago

Chicago is a vibrant, multicultural, and edgey 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 museums, theater, and nightlife.

Islamorada and Chicago: Pros and Cons

Is there more to do in Islamorada or Chicago?

Visitors will usually find more to do in Chicago than Islamorada, as it offers more sights, attractions, and activities. Chicago is better known for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Islamorada is more popular for its resorts, scuba diving & snorkeling, beaches, and impressive beauty. Islamorada is well known for its sportfishing, state parks, and local vibe. 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).

How is Islamorada different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is renowned for its historical sights. Also, Islamorada is not as popular, but is still a nice village 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).

Islamorada offers a variety of museums and landmarks to choose from. There are a variety of museums and aquariums in the area such as the History of Diving Museum, the Keys History and Discovery Center, and the famous Theater of the Sea.

Is Islamorada or Chicago Better for Theater?

Chicago is renowned for theatre. However, Islamorada 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.

Islamorada is not a theatre destination.

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

Chicago is renowned for its local flavors and cuisine. Also, Islamorada is not as popular, but is still a nice village 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.

Eating is part of the travel experience when you visit Islamorada. Has a sports fishing destination, you'll find no shortage of seafood options in the area. There are cafes and bistros that have an old school Florida Key's atmosphere. Popular dishes include grilled fish and curry seafood.

Is Islamorada or Chicago Better for Nightlife?

Chicago is renowned for nightlife. Also, Islamorada is not as popular, but is still a nice village for nightlife and partying.

Chicago is a destination that you simply have to visit at least once for nightlife. 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 Islamorada. The nightlife consists of mostly bars and restaurants that serve cocktails and frozen drinks. There are sports bars and casual eateries where you can enjoy a drink in a relaxed atmosphere.

Is Islamorada or Chicago Better for Music?

Chicago is renowned for live music. However, Islamorada 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.

Islamorada is not a live music destination.

Is Islamorada or Chicago Better for Resorts?

Islamorada is very good for its resorts. However, Chicago is not a resort destination.

Islamorada has a few great resort options. You'll find plenty of resorts with spas, pools or oceanfront views in the area.

Chicago is not a resort destination.

Is Islamorada or Chicago Better for Scuba Diving and Snorkeling?

Islamorada 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 Islamorada. There are plenty of dive shops that offer snorkeling and dive trips to the surrounding areas. You could also grab a mask and head out into the water on your own. You're sure to see some beautiful marine life.

Chicago is not a scuba or snorkeling destination.

Is Islamorada or Chicago Better for Beaches?

Islamorada is a great destination for the beach. Also, Chicago is still popular, but not quite as popular for its beaches.

Islamorada is a very popular place to visit for its beaches. Blue water and white sand make the beaches a true paradise. Favorite beaches in the area include Anne's Beach, which has a boardwalk and mangroves, Library Beach, which is small and well maintained, Holiday Isle Beach, which is near the hotels and restaurants, and Long Key State Park, which has camping and picnic spots.

Chicago has a beach worth visiting. 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 Islamorada or Chicago?

Chicago is renowned for shopping. Also, Islamorada is not as popular, but is still a nice village 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.

Islamorada offers some nice shopping areas. You'll find a few jewelry boutiques as well as sporting goods shops and souvenir stands.

Is Islamorada or Chicago Better for Christmas?

Chicago is a great city for its Christmas holiday experiences. However, Islamorada 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.

Islamorada does not offer Christmas activities.

Is Islamorada or Chicago Better for Christmas Markets?

Chicago is a nice place to visit for visiting Christmas markets. However, Islamorada 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.

Islamorada does not offer Christmas markets.

Is Islamorada or Chicago Better for Families?

Islamorada and Chicago are both terrific destinations for the whole family.

Islamorada is an amazing family-friendly village to visit. Theater of the Sea is a highlight for kids and adults alike. You'll have the opportunity to interact with many types of sea life including dolphins, sea lions, and even sharks. Founders Park is another great place to take the kids. You can have a picnic, hang out at the beach, or hit up the playground. There's also plenty of snorkeling and diving in the area, particularly around Alligator Reef Lighthouse.

Chicago is an extremely popular village 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.

Is Islamorada or Chicago Better for Couples?

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

For those traveling as a couple, Islamorada has plenty to offer. Couples will enjoy the resorts, spas, beaches, and adventures in the area. Head to Little Palm Spa for a little relaxation or hit up Florida Keys Brewing Company for some live music. There's also snorkeling, diving, and some good restaurants nearby as well.

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 Islamorada or Chicago Better for Backpackers and Budget Travelers?

Chicago is a nice place to visit for backpackers and budget travelers. However, Islamorada is not known for backpackers.

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.

Islamorada is a challenging destination for budget travelers and backpackers due to the higher prices. There aren't any real hostels on this key and prices in general can be a bit high so backpackers will find it a bit challenging.

Is Islamorada or Chicago Better for Students?

Chicago is renowned for its student-friendly activities. However, Islamorada 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.

Islamorada is not popular with students.

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

Chicago is renowned for times when you don't have a car. However, Islamorada is not known for its public transit.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is limited or non-existant in Islamorada. There's no real public transit in the area and you must have your own vehicle.

Is Islamorada or Chicago a more walkable city?

Chicago is a great city for its walkability. However, Islamorada is not known for its high level of walkability.

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

Islamorada is not a walkable village. Like the rest of the Florida Keys, it's not very walkable and you'll need a car to get around.

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

Should I spend more time in Chicago or Islamorada?

How long in Islamorada or Chicago?

In either Islamorada or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Islamorada than Chicago because of the overall number of sights and activities. Usually, 4-7 days is a good amount of time for Islamorada, and 3-5 days is enough time in Chicago.

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

In Islamorada, you'll find shopping and museums. You'll find plenty of activities on the beach. This village offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

When visiting Chicago, people usually allow for lots of time. Anyone can find something fun to do here. But since there are so many activities, you'll likely want to spend more than one day exploring.

A weekend in Islamorada or Chicago?

In Islamorada, you'll find museums and nightlife. The length of your trip often depends on your style of travel. Most people come for the beaches. Since there is so much to do in the area, a weekend is probably not enough for all of it.

When visiting Chicago, people usually allow for lots of time. It offers something for everyone. With so much to do, a weekend is probably not enough time to see everything.

Five days in Islamorada or Chicago?

Islamorada is a great place to explore. It is common to spend five days here. Many visitors spend time at the beach while visiting the area. Five days is a great amount of time to relax and see the many things that Islamorada has to offer. Anyone can find something fun to do here.

Chicago, a popular city, is full of activities for travelers. This is a popular place to visit for five days. In five days, you should have a good grasp of this city. Your budget might influence how long you stay.

A week in Islamorada or Chicago?

It's hard to know how much time to spend in Islamorada. In Islamorada, you'll find food and scuba diving and snorkeling. People usually spend lots of time at the beach. With all of its activities, you can easily fill one week here.

Chicago is a popular place that is full of things to see and experience. One week is plenty of time to see everything, even with extra days to spare. It has many unique tourist attractions and fascinating things to do.

For some great organized tour ideas, see The Best 3-Week Tours in United States of America, The Best Bicycle Tours in United States of America, Tours for Outdoor and Nature Lovers in United States of America, and The Best Coach Bus Tours in United States of America.

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

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

Which is Bigger, Islamorada or Chicago?

Chicago has a larger population, and is about 400 times larger than the population of Islamorada. When comparing the sizes of Islamorada 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.

When is the best time to visit Islamorada or Chicago?

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 Islamorada or Chicago in the Summer?

The summer brings many poeple to Islamorada as well as Chicago. Most visitors come to Islamorada for the beaches, snorkeling, and the family-friendly experiences during these months. Additionally, the summer months attract visitors to Chicago because of the beaches, the city activities, the music scene, and the family-friendly experiences.

In July, Islamorada is generally a little warmer than Chicago. Daily temperatures in Islamorada average around 84°F (29°C), and Chicago fluctuates around 77°F (25°C).

The sun comes out a lot this time of the year in Chicago. People are often attracted to the plentiful sunshine in Islamorada this time of the year. In the summer, Islamorada often gets around the same amount of sunshine as Chicago. Islamorada gets 328 hours of sunny skies this time of year, while Chicago receives 326 hours of full sun.

It's quite rainy in Chicago. Islamorada usually gets less rain in July than Chicago. Islamorada gets 3.3 inches (83 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.

Should I visit Islamorada or Chicago in the Autumn?

Both Chicago and Islamorada are popular destinations to visit in the autumn with plenty of activities. The autumn months attract visitors to Islamorada because of the shopping scene and the natural beauty of the area. Also, the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area are the main draw to Chicago this time of year.

Islamorada is much warmer than Chicago in the autumn. The daily temperature in Islamorada averages around 80°F (27°C) in October, and Chicago fluctuates around 56°F (14°C).

The sun comes out a lot this time of the year in Islamorada. Islamorada usually receives more sunshine than Chicago during autumn. Islamorada gets 258 hours of sunny skies, while Chicago receives 195 hours of full sun in the autumn.

It's quite rainy in Islamorada. In October, Islamorada usually receives more rain than Chicago. Islamorada gets 5.1 inches (129 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn. The hurricane season in Islamorada is June to November.

Should I visit Islamorada or Chicago in the Winter?

Both Chicago and Islamorada during the winter are popular places to visit. The museums, the shopping scene, and the cuisine are the main draw to Islamorada this time of year. Also, many travelers come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Be prepared for some very cold days in Chicago. In the winter, Islamorada is much warmer than Chicago. Typically, the winter temperatures in Islamorada in January average around 70°F (21°C), and Chicago averages at about 25°F (-4°C).

It's quite sunny in Islamorada. In the winter, Islamorada often gets more sunshine than Chicago. Islamorada gets 252 hours of sunny skies this time of year, while Chicago receives 134 hours of full sun.

Islamorada usually gets less rain in January than Chicago. Islamorada gets 1.7 inches (43 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.

Should I visit Islamorada or Chicago in the Spring?

The spring attracts plenty of travelers to both Islamorada and Chicago. Many travelers come to Islamorada for the beaches and the natural beauty. Also, many visitors come to Chicago in the spring for the beaches, the activities around the city, and the natural beauty.

In April, Islamorada is generally much warmer than Chicago. Daily temperatures in Islamorada average around 77°F (25°C), and Chicago fluctuates around 52°F (11°C).

People are often attracted to the plentiful sunshine in Chicago this time of the year. In Islamorada, it's very sunny this time of the year. Islamorada usually receives more sunshine than Chicago during spring. Islamorada gets 326 hours of sunny skies, while Chicago receives 218 hours of full sun in the spring.

Chicago receives a lot of rain in the spring. In April, Islamorada usually receives less rain than Chicago. Islamorada gets 0.8 inches (21 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring. June to November is the hurricane season in Islamorada.

Typical Weather for Chicago and Islamorada