A Travel Price Comparison for United States of America Key West vs. Chicago for Food, Nightlife, Families, and Beaches

Should you visit Key West or Chicago?

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

Should I visit Key West 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.

Key West

Key West is a quirky, eclectic, and bustling town. Don't miss this spot, as it's a charming small town with plenty of activities. With stunning beauty, it attracts visitors from all around. With a quaint atmosphere, it also offers a unique feeling. Other popular activities here include scuba diving and snorkeling, beaches, and nightlife.

Chicago

Chicago is a cosmopolitan, diverse, and vibrant city. With plenty of activities and things to do, it's a huge city that draws plenty of visitors. It's a beautiful place to visit, too. And you can't forget about the museums, theater, and nightlife.

Key West and Chicago: Pros and Cons

Is there more to do in Key West or Chicago?

Tourists will generally find more to do in Chicago. Although Key West and Chicago are both popular with visitors, Chicago has more sights, activities, and attractions for travelers. Chicago is more popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, and big city activities, while Key West is known for its resorts, scuba diving & snorkeling, beaches, historical sights, small town charm, impressive beauty, and quaint atmosphere. Key West is more touristy than Chicago and is known for its festive nightlife, quirky town center, colorful personality, adrenaline-filled watersports, stunning beaches, turquoise water, and location at the southernmost point of the continental U.S. Chicago is popular for its thriving sports scene, its iconic local cuisine, and its world class shopping at the Magnificent Mile. It is also home to The Willis Tower (previously the Sears Tower).

How is Key West different from Chicago?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Key West or Chicago?

Chicago is renowned for its sights and museums. However, Key West does not have museums and landmarks.

The museums, monuments, and landmarks in Chicago are among the most recognizable in the world. 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).

Key West does not have museums and landmarks.

Is Key West or Chicago Better for Theater?

Chicago is renowned for its theatre productions. However, Key West 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.

Key West is not a theatre destination.

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

Chicago is renowned for its local cuisine and restaurants. Also, Key West is not as famous, but is still a good town to visit for its 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.

Key West is becoming an appealing option for foodies. Head to town for local restaurants with quirky atmospheres. There are many local dishes to sample, be the town is most known for its stone crabs, conch fritters, and Mahi Mahi sandwiches. You'll also find cold drinks and waterfront dining areas.

Is Key West or Chicago Better for Nightlife?

Chicago is renowned for nightlife and partying. Also, Key West is not as famous, but is still a good town to visit for its evening party scene.

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.

Key West has a lively atmosphere and nightlife is popular here. This area has some of the most lively nightlife in the Florida Keys. There are quirky bars and fun hangouts where you can spend the evening. The party starts at Mallory Square around sunset and many bars stay open well into the early hours. You can also enjoy sunset cruises or pass your time at one of the many tiki bars.

Is Key West or Chicago Better for Music?

Chicago is renowned for its live music scene. However, Key West is not a live music destination.

Live music, and music in many other forms, is everyone in Chicago The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Key West is not a live music destination.

Is Key West or Chicago Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Key West. There are a number of high end resorts around the island, many with recognizable names such as the Hyatt and Hilton. Prices can be high, but these resorts often come with reliable luxury.

Chicago is not a resort destination.

Is Key West or Chicago Better for Scuba Diving and Snorkeling?

Key West 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 Key West. There are a number of dive shops and snorkeling excursions that leave from Key West. Like many tourist areas these days, the coral shows its damage from the crowds, but you'll likely see some barracuda or a Grouper.

Chicago is not a scuba or snorkeling destination.

Is Key West or Chicago Better for Beaches?

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

Key West is a very popular place to visit for its beaches. One of the best beaches in the area is Fort Zachary Taylor Historic State Park. The beach has soft sand and stunning turquoise water. As is typical in the Keys, the water stays shallow for great distances.

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 Key West or Chicago Better for its Old Town?

Key West is a great destination for its historic old town charm. However, Chicago does not have a historic old town.

There is a nice variety of sights in the old town of Key West. The town has the most charming Old Town areas in the Florida Keys. Head to Mallory Square for the sunset street performers and explore the historic streets around Duval Street.

Chicago does not have a historic old town.

Is the Shopping Better in Key West or Chicago?

Chicago is renowned for its shopping opportunities. However, Key West is a mediocre town for its shopping areas.

The abundance of shops in Chicago make it a world-class shopping destination. 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.

Key West has some good spots for those that want to go shopping. While it definitely has its share of gimmicky souvenir shops and t-shirt stores, there are still a number of art galleries and local shops around Key West where you can enjoy shopping.

Is Key West or Chicago Better for Christmas?

Chicago is notable for its Christmas activities. However, Key West 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.

Key West does not offer Christmas activities.

Is Key West or Chicago Better for Christmas Markets?

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

Key West does not offer Christmas markets.

Is Key West or Chicago Better for Families?

Chicago is renowned for its family-friendly activities. Also, Key West is not as famous, but is still a good town to visit for its kid-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.

You'll find plenty of family-friendly things to do in Key West. Families that enjoy snorkeling, aquariums, water sports, and exploring new places will enjoy visiting this part of the Florida Keys. There are many ways to get out on the water from kayaking and snorkeling to glass bottom boat tours and sunset cruises. There are also many kid-friendly beaches in the area. The town can have a party atmosphere, but it's not hard to find a more family-friendly area where everyone can have fun.

Is Key West or Chicago Better for Couples?

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

Couples visit Key West frequently as it offers plenty of romantic activities. From Mallory Square to the beautiful nearby parks, Key West makes a wonderful, romantic destination. Whether it's your honeymoon, an anniversary, or simply a couples' retreat, Key West is a great option. You can sip wine on a sunset cruise or dine at one of the many character-filled restaurants in town. If you are looking for a party, it's not hard to find, but if you want a more laid back holiday, that's also possible.

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 Key West or Chicago Better for Backpackers and Budget Travelers?

Chicago is a popular place for backpackers. However, Key West is a mediocre town for backpackers and budget travelers.

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.

Key West is a challenging destination for budget travelers and backpackers due to the higher prices. Key West is a pretty expensive destination, but there are Airbnbs and even a hostel or two that cater to budget backpackers.

Is Key West or Chicago Better for Students?

Chicago is renowned for students. Also, Key West is not as famous, but is still a good town to visit for its student-friendly activities.

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.

Key West is very popular with students. It's a great spring break destination with a quirky personality and many great activities.

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

Chicago is renowned for its public transit. However, Key West is a mediocre town for times when you don't have a car.

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 quite limited in Key West. Public transportation in Key West is limited to a few buses.

Is Key West or Chicago a more walkable city?

Chicago is notable for its high level of walkability. Also, Key West is not as famous, but is still a good town to visit for its ease of walking around.

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

Key West is a somewhat walkable town. The town is the most walkable part of the Florida Keys. The area around Mallory Square and Duval Street is the most pedestrian friendly.

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

Should I spend more time in Chicago or Key West?

How long in Key West or Chicago?

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

Families should spend more time in Chicago than Key West. 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 Key West. 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 Key West 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 Key West or Chicago?

In Key West, you'll find scuba diving and snorkeling and nightlife. 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.

Chicago is a big city with plenty to do. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

A weekend in Key West or Chicago?

In Key West, you'll find nightlife and food. The length of your trip often depends on your style of travel. Visiting the old town is also a must. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Chicago is a popular place that is full of things to see and experience. But since there are so many activities, you'll likely want to spend more than a weekend exploring. Take your pick from the many activities offered here.

Five days in Key West or Chicago?

Key West 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 Key West has to offer. Anyone can find something fun to do here.

Chicago is a popular choice for travelers. Five days here is typical. While some people choose to spend more or less time in Chicago, five days is sufficent for most. The entire region has so many activities, and you'll want time to do everything.

A week in Key West or Chicago?

It's hard to know how much time to spend in Key West. In Key West, you'll find scuba diving and snorkeling and nightlife. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.

Chicago is a great place to explore. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This city offers something for everyone.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, The Best 2-Week Tours from New York City, and The Best 2-Week Tours from Anchorage.

When we compare the travel costs of actual travelers between Key West and Chicago, we can see that Key West is more expensive. And not only is Chicago much less expensive, but it is actually a significantly cheaper destination. So, traveling to Chicago would let you spend less money overall. Or, you could decide to spend more money in Chicago 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 Key West would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Key West than you might in Chicago.

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

Which is Bigger, Key West or Chicago?

Chicago has a larger population, and is about 120 times larger than the population of Key West. When comparing the sizes of Key West 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 Key West or Chicago?

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 Key West or Chicago in the Summer?

The summer attracts plenty of travelers to both Key West and Chicago. The beaches, snorkeling, the small town charm, and the family-friendly experiences are the main draw to Key West this time of year. Also, many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.

In the summer, Key West is a little warmer than Chicago. Typically, the summer temperatures in Key West in July average around 84°F (29°C), and Chicago averages at about 77°F (25°C).

People are often attracted to the plentiful sunshine in Chicago this time of the year. In Key West, it's very sunny this time of the year. Key West usually receives around the same amount of sunshine as Chicago during summer. Key West gets 328 hours of sunny skies, while Chicago receives 326 hours of full sun in the summer.

Chicago receives a lot of rain in the summer. In July, Key West usually receives less rain than Chicago. Key West gets 3.3 inches (83 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.

Should I visit Key West or Chicago in the Autumn?

The autumn brings many poeple to Key West as well as Chicago. Many travelers come to Key West for the shopping scene, the small town atmosphere, and the natural beauty of the area. Also, 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.

In October, Key West is generally much warmer than Chicago. Daily temperatures in Key West average around 80°F (27°C), and Chicago fluctuates around 56°F (14°C).

People are often attracted to the plentiful sunshine in Key West this time of the year. In the autumn, Key West often gets more sunshine than Chicago. Key West gets 258 hours of sunny skies this time of year, while Chicago receives 195 hours of full sun.

Key West receives a lot of rain in the autumn. Key West usually gets more rain in October than Chicago. Key West gets 5.1 inches (129 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year. Also, June to November in Key West is the hurricane season.

Should I visit Key West or Chicago in the Winter?

Both Chicago and Key West are popular destinations to visit in the winter with plenty of activities. Many visitors come to Key West in the winter for the shopping scene and the cuisine. Also, most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.

Chicago can be very cold during winter. Key West is much warmer than Chicago in the winter. The daily temperature in Key West averages around 70°F (21°C) in January, and Chicago fluctuates around 25°F (-4°C).

The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Chicago during winter. Key West gets 252 hours of sunny skies, while Chicago receives 134 hours of full sun in the winter.

In January, Key West usually receives less rain than Chicago. Key West gets 1.7 inches (43 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.

Should I visit Key West or Chicago in the Spring?

Both Chicago and Key West during the spring are popular places to visit. Most visitors come to Key West for the beaches, the small town charm, and the natural beauty during these months. Furthermore, the spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.

In the spring, Key West is much warmer than Chicago. Typically, the spring temperatures in Key West in April average around 77°F (25°C), and Chicago averages at about 52°F (11°C).

In Chicago, it's very sunny this time of the year. It's quite sunny in Key West. In the spring, Key West often gets more sunshine than Chicago. Key West gets 326 hours of sunny skies this time of year, while Chicago receives 218 hours of full sun.

Chicago gets a good bit of rain this time of year. Key West usually gets less rain in April than Chicago. Key West gets 0.8 inches (21 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year. Also, the hurricane season in Key West is June to November.

Typical Weather for Chicago and Key West