A Travel Price Comparison for United States of America Destin vs. Chicago for Food, Families, Beaches, and Couples

Should you visit Destin or Chicago?

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

Destin

Destin is a beautiful, relaxing, and peaceful beach town. It offers plenty of beauty for visitors. Other popular activities here include shopping, food, and beaches.

Chicago

Chicago is a diverse, vibrant, and multicultural city. It's an amazing and huge city with tons of activities and things to do. It's a gorgeous place to visit. It's also known for shopping, museums, and theater.

Destin and Chicago: Pros and Cons

Is there more to do in Destin or Chicago?

Visitors will usually find more to do in Chicago than Destin, 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 Destin is more popular for its resorts and beaches. Destin is well known for its powdery sand and turquoise water, its kid-friendly environment, and its local waterfront seafood restaurants. 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 Destin different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is terrific for its sights and museums. However, Destin 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).

Destin does not have museums and landmarks.

Is Destin or Chicago Better for Theater?

Chicago is terrific for theatre. However, Destin is not a theatre destination.

The theater scene in Chicago is world-class. 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.

Destin is not a theatre destination.

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

Chicago is terrific for its local cuisine and restaurants. Also, Destin is not as famous, but is still a good beach town to visit for its restaurants.

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.

Destin has a delicious restaurant scene that relies on local flavors. The area has great seafood including crab chowder, seafood gumbo, and fried fish. You can find wonderful local restaurants that have waterfront views and menus that feature freshly caught seafood. Many restaurants also have kid-friendly menus. During peak season, reservations are recommended.

Is Destin or Chicago Better for Nightlife?

Chicago is terrific for nightlife. However, Destin is a mediocre beach town for nightlife and partying.

Chicago is a must-see 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.

Destin doesn't offer many options. The region is more popular as a family-friendly beach destination than it is for it's nightlife. Head to the Harbor area for the most lively nightlife.

Is Destin or Chicago Better for Music?

Chicago is terrific for live music. However, Destin 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.

Destin is not a live music destination.

Is Destin or Chicago Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Destin. Popular options include the Sandestin Golf & Beach Resort, as well as Hilton Sandestin Beach, Golf Resort & Spa. Most of the accommodation in the area is in the form of condos that include a kitchen and separate bedrooms. Most of these complexes also have pools, hot tubs, and even kids clubs.

Chicago is not a resort destination.

Is Destin or Chicago Better for Beaches?

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

Destin is a very popular place to visit for its beaches. This area is famous for its powdery white sand, beautiful blue waters, and calm waves. The beaches are large enough that they never get incredibly crowded, but you will find the largest crowds during the summer months. These beaches are particularly popular with families and seniors.

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 Destin or Chicago?

Chicago is terrific for shopping. Also, Destin is not as famous, but is still a good beach town to visit for its shopping opportunities.

Chicago is a famous shopping destination with plenty of stores. 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.

Shopping is a popular activity when visiting Destin. In the shopping centers around town you'll find a number of unique boutique shops that are fun to explore. They have boutique-style beach clothes, local art, and any beach supplies that you may have forgotten.

Is Destin or Chicago Better for Christmas?

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

Destin does not offer Christmas activities.

Is Destin or Chicago Better for Christmas Markets?

Chicago is very good for its Christmas markets. However, Destin does not offer Christmas markets.

Chicago offers some nice Christmas markets. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Destin does not offer Christmas markets.

Is Destin or Chicago Better for Families?

Chicago is terrific for its family-friendly activities. Also, Destin is not as famous, but is still a good beach town to visit for its kid-friendly activities.

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.

Because of its large number of kid-friendly activities, Destin is very family-friendly. The area has beautiful sandy beaches, calm waters, and plenty of activities for kids like Big Kahuna's Water Park. This is one of the more kid-friendly areas in Florida and many families return year after year with their kids. There are also many condos available for rent and kids can have their own room, kitchens are available for meal preparation, and there are washers and dryers to clean clothes. Many of these condo complexes also have kid-friendly pools

Is Destin or Chicago Better for Couples?

Both Destin and Chicago are notable destinations to visit as a couple.

Destin is a nice destination for couples. For a relaxing beach vacation, this is a nice option for couples. A lot of the accommodation is in the form of condos, so it may not have the romantic resort vibe you're going for though. There are many great seafood restaurants and quiet beaches that have beautiful sunsets.

Chicago makes for a fun place to visit for a couple. 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 Destin or Chicago Better for Backpackers and Budget Travelers?

Chicago is very good for backpackers. However, Destin is not a backpacker-friendly destination.

Chicago is popular with backpackers and budget travelers. The city doesn't have a huge backpacker vibe, but it does have a number of hostels that help keep costs in check.

Destin is not a backpacker-friendly destination.

Is Destin or Chicago Better for Students?

Chicago is terrific for students. However, Destin is a mediocre beach town for its student-friendly activities.

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.

Destin is a decent spot for students. It is more a family-friendly destination than a spring break destination. If you're looking for a place to cut loose and blow off some steam, then there are better options in Florida.

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

Chicago is terrific for its public transit. However, Destin is a mediocre beach town for times when you don't have a car.

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.

Public transit is quite limited in Destin. There is almost no public transit so a car is essential. Some condo complexes do over golf carts to get around the grounds.

Is Destin or Chicago a more walkable city?

Chicago is notable for its walkability. However, Destin is a mediocre beach 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.

Destin is not a very walkable beach town. The area is very spread out and not walkable so you'll need a car to access restaurants and most forms of entertainment.

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

Should I spend more time in Chicago or Destin?

How long in Destin or Chicago?

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

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

In Destin, you'll find food and shopping. Travelers enjoy the resorts in the area as well. This beach 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 bustling city that offers something for everyone. But since there are so many activities, you'll likely want to spend more than one day exploring.

A weekend in Destin or Chicago?

In Destin, you'll find shopping and food. 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.

Chicago is a great place to explore. With so much to do, a weekend is probably not enough time to see everything. Your budget might influence how long you stay.

Five days in Destin or Chicago?

Destin 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 Destin has to offer. Anyone can find something fun to do here.

It's hard to know how much time to spend in Chicago. For many, it makes a great getaway for five days. With all of its activities, you can easily fill five days here. It has many unique tourist attractions and fascinating things to do.

A week in Destin or Chicago?

It's hard to know how much time to spend in Destin. In Destin, you'll find shopping and food. It's also a relaxing resort destination. With all of its activities, you can easily fill one week here.

Travelers enjoy the museums and theater when visiting the edgey big city of Chicago. This city offers a variety of activities to choose from. Most people find that one week is more than enough time to see everything.

For some great organized tour ideas, see The Best Walking Tours in United States of America, The Best Tours Under $1000 in United States of America, The Best Luxury Tours to United States of America, and The Best Tours for Seniors to United States of America.

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

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

Which is Bigger, Destin or Chicago?

Chicago has a larger population, and is about 230 times larger than the population of Destin. When comparing the sizes of Destin 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 Destin 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 Destin or Chicago in the Summer?

The summer attracts plenty of travelers to both Destin and Chicago. The summer months attract visitors to Destin because of the beaches and the family-friendly experiences. Also, the beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Chicago this time of year.

In July, Destin is generally around the same temperature as Chicago. Daily temperatures in Destin average around 82°F (28°C), and Chicago fluctuates around 77°F (25°C).

Chicago receives a lot of rain in the summer. Destin gets a good bit of rain this time of year. In July, Destin usually receives more rain than Chicago. Destin gets 7.4 inches (189 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain each month for the summer.

Should I visit Destin or Chicago in the Autumn?

The autumn brings many poeple to Destin as well as Chicago. The shopping scene and the natural beauty of the area are the main draw to Destin this time of year. Also, many travelers come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

Destin is much warmer than Chicago in the autumn. The daily temperature in Destin averages around 69°F (21°C) in October, and Chicago fluctuates around 56°F (14°C).

Destin receives a lot of rain in the autumn. Destin usually gets more rain in October than Chicago. Destin gets 4.2 inches (107 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year.

Should I visit Destin or Chicago in the Winter?

Both Chicago and Destin are popular destinations to visit in the winter with plenty of activities. Many travelers come to Destin for the shopping scene and the cuisine. Also, many visitors come to Chicago in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Chicago can get quite cold in the winter. In the winter, Destin is much warmer than Chicago. Typically, the winter temperatures in Destin in January average around 50°F (10°C), and Chicago averages at about 25°F (-4°C).

It's quite rainy in Destin. In January, Destin usually receives more rain than Chicago. Destin gets 4.6 inches (117 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain each month for the winter.

Should I visit Destin or Chicago in the Spring?

Both Chicago and Destin during the spring are popular places to visit. Many visitors come to Destin in the spring for the beaches and the natural beauty. Furthermore, most visitors come to Chicago for the beaches, the activities around the city, and the natural beauty during these months.

In April, Destin is generally much warmer than Chicago. Daily temperatures in Destin average around 68°F (20°C), and Chicago fluctuates around 52°F (11°C).

Chicago gets a good bit of rain this time of year. Destin usually gets less rain in April than Chicago. Destin gets 3.4 inches (87 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year.

Typical Weather for Chicago and Destin