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

Should you visit Pensacola 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 Pensacola and Chicago can help you decide which place is right for you.

Pensacola

Pensacola is a entertaining, fun-filled, and active beach town. Other popular activities here include shopping, museums, and nightlife.

Chicago

Chicago is a diverse, vibrant, and multicultural 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 live music, food, and beaches.

Pensacola and Chicago: Pros and Cons

Is there more to do in Pensacola or Chicago?

Travelers will usually find more to do in Chicago than Pensacola, as it is bigger with more sights, attractions, and activities for visitors. Chicago is more popular for its museums, theatre productions, food, nightlife, music, shopping, christmas markets, big city activities, and impressive beauty, while Pensacola is known for its resorts, beaches, and hiking. Pensacola is more touristy than Chicago and is known for its white sand beaches and long running naval history. 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 Pensacola different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is a world-class destination for its sights and museums. Also, Pensacola is not as famous, but is still a good beach town to visit for its museums and history.

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).

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Pensacola. On a rainy day there are some nice museums in the area. You can visit the National Naval Aviation Museum, the Historic Pensacola Village, the Pensacola Lighthouse and Museum, or Pensacola Children's Museum.

Is Pensacola or Chicago Better for Theater?

Chicago is a world-class destination for its theatre productions. However, Pensacola 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.

Pensacola is not a theatre destination.

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

Chicago is a world-class destination for its local cuisine and restaurants. Also, Pensacola 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.

Pensacola has a number of nationally recognized food spots and restaurants. You'll find no shortage of seafood options around town. Oysters, shrimp, and fresh fish are popular on the menus. You'll also find lots of Cajun flavors as well as casual sandwiches and pizza.

Is Pensacola or Chicago Better for Nightlife?

Chicago is a world-class destination for nightlife and partying. Also, Pensacola is not as famous, but is still a good beach town to visit for its evening party scene.

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.

With a handful of venues, visitors can find a fairly lively vibe in Pensacola. There's a casual nightlife scene with pubs, live music, and a mellow but fun setting.

Is Pensacola or Chicago Better for Music?

Chicago is a world-class destination for its live music scene. However, Pensacola 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.

Pensacola is not a live music destination.

Is Pensacola or Chicago Better for Resorts?

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

Vacationers can choose from a number of terrific resorts in Pensacola. Family-friendly resorts with pools, waterslides, and lazy rivers are common. You'll also find beachfront hotels and more affordable options set back from the beach.

Chicago is not a resort destination.

Is Pensacola or Chicago Better for Beaches?

Pensacola is renowned for the beach. Also, Chicago is still popular, but not quite as popular for its beaches.

With world-famous beaches, Pensacola is a very popular vacation destination. White sand beaches with blue water and mild temperatures make this a wonderful beach destination. Some of the best beaches include Casino Beach, Perdido Key Beach, and Opal Beach.

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 Pensacola or Chicago Better for Hiking?

Pensacola is a beach town with a few options for its hiking experiences. However, Chicago is not a hiking destination.

Hiking is a fun activity while in Pensacola. Step away from the beachfront development and you'll find some nice nature parks with quiet walking trails.

Chicago is not a hiking destination.

Is the Shopping Better in Pensacola or Chicago?

Chicago is a world-class destination for its shopping opportunities. Also, Pensacola is not as famous, but is still a good beach town to visit 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.

Pensacola has a variety of shopping areas worth visiting. There are sprawling shopping malls and shopping centers as well as local boutiques and quintessential souvenir shops.

Is Pensacola or Chicago Better for Christmas?

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

Pensacola does not offer Christmas activities.

Is Pensacola or Chicago Better for Christmas Markets?

Chicago is very good for its Christmas markets. However, Pensacola 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.

Pensacola does not offer Christmas markets.

Is Pensacola or Chicago Better for Families?

Chicago is a world-class destination for its family-friendly activities. Also, Pensacola 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.

You'll find plenty of family-friendly things to do in Pensacola. Kid-friendly beaches, minigolf, a zoo, and even a few museums make this a great family destination. There are family-friendly resorts and kid-friendly restaurants that make for an easy vacation that everyone will enjoy.

Is Pensacola or Chicago Better for Couples?

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

Couples visit Pensacola frequently as it offers plenty of romantic activities. Beautiful beaches and sunset cruises make this a great romantic getaway. You'll find great restaurants for a date night and plenty of activity once the sun goes down. During the day you can lounge on the beach or by the pool, sip drinks, and enjoy a vacation with your loved one.

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 Pensacola or Chicago Better for Backpackers and Budget Travelers?

Chicago is very good for backpackers. However, Pensacola is a mediocre beach town for backpackers and budget travelers.

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.

Pensacola is a challenging destination for budget travelers and backpackers due to the higher prices. There are a few budget-friendly places to stay, particularly away from the beach.

Is Pensacola or Chicago Better for Students?

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

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.

Pensacola is not popular with students.

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

Chicago is a world-class destination for its public transit. However, Pensacola is a mediocre beach town 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 Pensacola. There's a bus system, but it's not particularly helpful to vacationers.

Is Pensacola or Chicago a more walkable city?

Chicago is notable for its high level of walkability. However, Pensacola is a mediocre beach town 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.

Pensacola is generally not a very walkable beach town. It's not a particularly walkable city and you'll want to have a car to fully enjoy your vacation.

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

Should I spend more time in Chicago or Pensacola?

How long in Pensacola or Chicago?

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

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

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

People visit Chicago because there is so much to do. Since there is so much to do in the area, one day is probably not enough for all of it. It has many unique tourist attractions and fascinating things to do.

A weekend in Pensacola or Chicago?

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

People visit Chicago because there is so much to do. A weekend is usually not enough time for a trip here as there is plenty to do. This city offers a variety of activities to choose from.

Five days in Pensacola or Chicago?

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

People visit Chicago because there is so much to do. The length of your ideal trip is an individual decision. If you have five days, this city makes for a great vacation. Five days should give you a good understanding of everything this city has to offer.

A week in Pensacola or Chicago?

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

Chicago is a popular choice for travelers. One week is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. It will give you the chance to have new experiences.

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 Pensacola and Chicago, we can see that Chicago is more expensive. And not only is Pensacola much less expensive, but it is actually a significantly cheaper destination. So, traveling to Pensacola would let you spend less money overall. Or, you could decide to spend more money in Pensacola 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 Pensacola.

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

Which is Bigger, Pensacola or Chicago?

Chicago has a larger population, and is about 50 times larger than the population of Pensacola. When comparing the sizes of Pensacola 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 Pensacola 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 Pensacola or Chicago in the Summer?

The summer attracts plenty of travelers to both Pensacola and Chicago. The summer months attract visitors to Pensacola because of the beaches, the hiking, 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 the summer, Pensacola is a little warmer than Chicago. Typically, the summer temperatures in Pensacola in July average around 82°F (28°C), and Chicago averages at about 77°F (25°C).

Chicago receives a lot of rain in the summer. Pensacola gets a good bit of rain this time of year. In July, Pensacola usually receives more rain than Chicago. Pensacola 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 Pensacola or Chicago in the Autumn?

The autumn brings many poeple to Pensacola as well as Chicago. The hiking trails and the shopping scene are the main draw to Pensacola 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.

In October, Pensacola is generally much warmer than Chicago. Daily temperatures in Pensacola average around 69°F (21°C), and Chicago fluctuates around 56°F (14°C).

Pensacola receives a lot of rain in the autumn. Pensacola usually gets more rain in October than Chicago. Pensacola gets 4.2 inches (107 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain this time of the year. Also, June to November in Pensacola is the hurricane season.

Should I visit Pensacola or Chicago in the Winter?

Both Chicago and Pensacola are popular destinations to visit in the winter with plenty of activities. Many travelers come to Pensacola for the museums, 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. Pensacola is much warmer than Chicago in the winter. The daily temperature in Pensacola averages around 51°F (10°C) in January, and Chicago fluctuates around 25°F (-4°C).

It's quite rainy in Pensacola. In January, Pensacola usually receives more rain than Chicago. Pensacola 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 Pensacola or Chicago in the Spring?

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

In the spring, Pensacola is much warmer than Chicago. Typically, the spring temperatures in Pensacola in April average around 67°F (20°C), and Chicago averages at about 52°F (11°C).

Chicago gets a good bit of rain this time of year. Pensacola usually gets less rain in April than Chicago. Pensacola gets 3.4 inches (87 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain this time of the year. Also, the hurricane season in Pensacola is June to November.

Typical Weather for Chicago and Pensacola