A Travel Price Comparison for Families, Couples, and Backpackers Tallinn vs. Chicago for Attractions, Food, Nightlife, and Families

Should you visit Tallinn or Chicago?

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

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

Tallinn

Tallinn is a quaint, whimsical, and historical city. The famous beauty of Tallinn is one of the main draws. As it offers a special and quaint atmosphere, visitors come from all over to experience this destination. Other popular activities here include shopping, museums, and nightlife. See Tallinn travel costs.

Chicago

Chicago is a vibrant, multicultural, and edgey city. With plenty of activities and things to do, it's a huge city that draws plenty of visitors. Chicago is a beautiful place to visit, too. Visitors also love the beaches, shopping, and museums. See Chicago travel costs.

Tallinn and Chicago: Pros and Cons

Is there more to do in Tallinn or Chicago?

Travelers will usually find more to do in Chicago than Tallinn, as it is bigger with more sights, attractions, and activities for visitors. Chicago is more popular for its museums and attractions, theatre productions, food, nightlife, music, beaches, shopping, christmas markets, and big city activities, while Tallinn is known for its historical sights, impressive beauty, and quaint atmosphere. Tallinn is more touristy than Chicago and is popular for its well preserved old town and its active nightlife scene. 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 Tallinn different from Chicago?

Which is Better for a Holiday?

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

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

Chicago is a must-visit destination for its museums and history. Also, Tallinn is not quite as popular, but is fairly good for its museums and landmarks.

The museums and tourist attractions in Chicago are world-renowned. 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).

You'll find a good number of museums and monuments packed into Tallinn. There are beautiful historic churches, particularly in the city's old town. A highlight is the stunning Alexander Nevski Cathedral. You'll also find some unique museums around town as well as Toompea Castle.

Is Tallinn or Chicago Better for Theater?

Chicago is a must-visit destination for its theatre productions. However, Tallinn 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.

Tallinn is not a theatre destination.

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

Chicago is a must-visit destination for its restaurants. Also, Tallinn is not quite as popular, but is fairly good for its restaurant scene.

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.

There are many up and coming restaurants in the Tallinn area. Food is affordable and hearty. Many dishes incorporate rye bread, pork, smoked fish, potatoes, or dairy products. You'll also find a lot of variation in dishes between seasons.

Is Tallinn or Chicago Better for Nightlife?

Chicago is a must-visit destination for nightlife and partying. Also, Tallinn is not quite as popular, but is fairly good for its evening party scene.

Chicago is a world class 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.

Tallinn is a popular destination for visitors looking to party into the night. As it's grown in popularity with tourists, the city has put itself on the map as a top party destination in Eastern Europe. There's an active bar and club scene, but there are also art venues and other creative activities for everyone.

Is Tallinn or Chicago Better for Music?

Chicago is a must-visit destination for its live music scene. However, Tallinn is not a live music destination.

With so many music venues, you're guaranteed a show any night of the week in Chicago. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

Tallinn is not a live music destination.

Is Tallinn or Chicago Better for Beaches?

Chicago is a nice place to visit for the beach. However, Tallinn is not a beach destination.

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.

Tallinn is not a beach destination.

Is Tallinn or Chicago Better for its Old Town?

Tallinn is renowned for its historic old town charm. However, Chicago does not have a historic old town.

The old town of Tallinn is one of the most recognized in the world. The city's medieval old town is at the heart of it's tourist attractions. The Gothic architecture, local restaurants, and cobblestone streets give the city a fairytale charm.

Chicago does not have a historic old town.

Is the Shopping Better in Tallinn or Chicago?

Chicago is a must-visit destination for its shopping opportunities. Also, Tallinn is not quite as popular, but is fairly good for its shopping areas.

Known for shopping, Chicago draws large crowds to its 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.

Browsing through shops is a popular activity in Tallinn. There's a mix of quirky shops and recognizable brands around town. Old town is a popular shopping area, as is nearby Kalamaja. Visitors enjoy picking up marzipan, local crafts, and unique art.

Is Tallinn or Chicago More Beautiful?

Tallinn is renowned for its scenery and beauty. Also, Chicago is still popular, but not quite as popular for its scenery and beauty.

The famous beauty of Tallinn is one of the main draws. The beautiful architecture and impressive old town makes this a top tourist destination in Eastern Europe.

Chicago is a gorgeous place to visit. The water makes this city a truly unique place to explore, and the world class architecture is not to be missed.

Is Tallinn or Chicago Better for Families?

Chicago is a must-visit destination for its kid-friendly activities. Also, Tallinn is not quite as popular, but is fairly good for its family-friendly activities.

Chicago is an amazing family-friendly city to visit. 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 kid-friendly things to do in Tallinn. Your kids will feel like they stepped into a fairytale in this beautiful city. It has countless museums including an open air museum and a zoo. There's also nearby Pirita Beach, where you and your kids can enjoy ice cream in a seaside setting.

Is Tallinn or Chicago Better for Couples?

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

Couples visit Tallinn frequently as it offers plenty of romantic activities. Filled with gardens, romantic walks, and impressive views, this city makes for a great couple's getaway. Base yourself in the city's beautiful old town and dine in one of the many local restaurants. There are also nice hotels around town that are great for couples.

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 Tallinn or Chicago Better for Backpackers and Budget Travelers?

Tallinn is renowned for backpackers. Also, Chicago is still popular, but not quite as popular for backpackers and budget travelers.

Tallinn is a very popular city to visit for backpackers. The city is both affordable and unique, which is perfect for travelers on a budget. There are plenty of hostels around town as well as casual places to grab a cheap bite to eat.

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.

Is Tallinn or Chicago Better for Students?

Chicago is a must-visit destination for its student-friendly activities. Also, Tallinn is not quite as popular, but is fairly good for 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.

Tallinn is popular with students. International students appreciate the vibrant atmosphere and the affordable options around town.

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

Chicago is a must-visit destination for times when you don't have a car. Also, Tallinn is not quite as popular, but is fairly good for its public transit.

Chicago has a world-class public transit network to take passengers everywhere in the city. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

The public transit in Tallinn can get you to most places easily. There are buses trolleys and trams around town.

Is Tallinn or Chicago a more walkable city?

Tallinn is renowned for its ease of walking around. Also, Chicago is still popular, but not quite as popular for its walkability.

Getting around Tallinn on foot is easy. The city is compact and easily explored on foot, particularly in the most touristy areas.

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

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

Should I spend more time in Chicago or Tallinn?

How long in Tallinn or Chicago?

In either Tallinn or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Chicago than Tallinn because of the overall number of sights and activities. Usually, 2-4 days is a good amount of time for Tallinn, and 3-5 days is enough time in Chicago.

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

In Tallinn, you'll find nightlife and food. Most visitors spend time around the old town while in the area. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

Because Chicago is a large city, there are a variety of ways to spend your time. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Tallinn or Chicago?

In Tallinn, you'll find food and shopping. The length of your trip often depends on your style of travel. A weekend here is typical. Visiting the old town is also a must. A weekend is a great amount of time to relax and see the many things that Tallinn has to offer.

Because Chicago is a large city, there are a variety of ways to spend your time. The length of your trip often depends on your style of travel. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Five days in Tallinn or Chicago?

Tallinn is a great place to explore. The old town is one of the main draws for visitors. 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.

Chicago is a great place to explore. It is common to spend five days here. Five days is a great amount of time to relax and see the many things that Chicago has to offer. Anyone can find something fun to do here.

A week in Tallinn or Chicago?

It's hard to know how much time to spend in Tallinn. Many people enjoy the museums and nightlife when visiting Tallinn. Exploring the old town is a popular activity. One week may feel like too much time unless you plan to do a lot of relaxing.

It's hard to know how much time to spend in Chicago. Many people enjoy the theater and nightlife when visiting Chicago. 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 2-Week Tours from Tallinn, The Best Family-Friendly Tours to Estonia, The Best 2-Week Tours from San Francisco, and The Best 2-Week Tours from Los Angeles.

When we compare the travel costs of actual travelers between Tallinn and Chicago, we can see that Chicago is more expensive. And not only is Tallinn much less expensive, but it is actually a significantly cheaper destination. Since Tallinn is in Europe and Chicago is in North America, this is one of the main reasons why the costs are so different, as different regions of the world tend to have overall different travel costs. So, traveling to Tallinn would let you spend less money overall. Or, you could decide to spend more money in Tallinn 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 Tallinn.

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

Which is Bigger, Tallinn or Chicago?

Chicago has a larger population, and is about 7 times larger than the population of Tallinn. When comparing the sizes of Tallinn 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 Tallinn 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 Tallinn or Chicago in the Summer?

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

In the summer, Tallinn is much colder than Chicago. Typically, the summer temperatures in Tallinn in July average around 17°C (62°F), and Chicago averages at about 77°F (25°C).

In Chicago, it's very sunny this time of the year. It's quite sunny in Tallinn. In the summer, Tallinn often gets less sunshine than Chicago. Tallinn gets 279 hours of sunny skies this time of year, while Chicago receives 326 hours of full sun.

Chicago gets a good bit of rain this time of year. Tallinn usually gets less rain in July than Chicago. Tallinn gets 79 mm (3.1 in) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.

Should I visit Tallinn or Chicago in the Autumn?

The autumn attracts plenty of travelers to both Tallinn and Chicago. The autumn months attract visitors to Tallinn because of the shopping scene and the natural beauty of the area. Furthermore, 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.

In October, Tallinn is generally much colder than Chicago. Daily temperatures in Tallinn average around 7°C (44°F), and Chicago fluctuates around 56°F (14°C).

Tallinn usually receives less sunshine than Chicago during autumn. Tallinn gets 92 hours of sunny skies, while Chicago receives 195 hours of full sun in the autumn.

In October, Tallinn usually receives more rain than Chicago. Tallinn gets 70 mm (2.8 in) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.

Should I visit Tallinn or Chicago in the Winter?

The winter brings many poeple to Tallinn as well as Chicago. The museums, the shopping scene, and the cuisine are the main draw to Tallinn this time of year. Additionally, 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. It's quite cold in Tallinn in the winter. Tallinn is cooler than Chicago in the winter. The daily temperature in Tallinn averages around -5°C (22°F) in January, and Chicago fluctuates around 25°F (-4°C).

In the winter, Tallinn often gets less sunshine than Chicago. Tallinn gets 25 hours of sunny skies this time of year, while Chicago receives 134 hours of full sun.

Tallinn usually gets around the same amount of rain in January as Chicago. Tallinn gets 45 mm (1.8 in) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.

Should I visit Tallinn or Chicago in the Spring?

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

Be prepared for some very cold days in Tallinn. In the spring, Tallinn is much colder than Chicago. Typically, the spring temperatures in Tallinn in April average around 4°C (39°F), and Chicago averages at about 52°F (11°C).

It's quite sunny in Chicago. Tallinn usually receives less sunshine than Chicago during spring. Tallinn gets 186 hours of sunny skies, while Chicago receives 218 hours of full sun in the spring.

It rains a lot this time of the year in Chicago. In April, Tallinn usually receives less rain than Chicago. Tallinn gets 36 mm (1.4 in) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.

Typical Weather for Chicago and Tallinn