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

Should you visit Chicago or Boston?

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

Chicago

Chicago is a edgey, cosmopolitan, and diverse 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 food, beaches, and shopping.

Boston

Boston is a proud, loyal, and historic city. As it's a big city, visitors will find plenty to do, too. It offers plenty of beauty for visitors. As this is a very quaint destination, you'll find it has a special atmosphere. Other popular activities here include food, shopping, and museums.

Chicago and Boston: Pros and Cons

Is there more to do in Chicago or Boston?

You'll generally find more things to do in Chicago than Boston. Chicago is bigger than Boston, and it also has more attractions and activities for travelers. Chicago is better known for its theatre productions, food, nightlife, music, beaches, shopping, and big city activities, while Boston is more popular for its historical sights, christmas markets, and quaint atmosphere. 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). Boston is well known for its enthusiastic sports fans, influential history, beautiful parks, and world-class universities.

How is Chicago different from Boston?

Which is Better for a Holiday?

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

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

For an educational experience, head to a museum or a notable sight in either Chicago or Boston.

You'll find many recognizable landmarks that put Chicago on the map. 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).

Travelers visit Boston from around the world to see its many world-famous attractions. The city itself feels like a living museum. It is famous for Faneuil Hall, the Museum of Fine Arts, the Isabelle Stewart Gardner Museum, the USS Constitution, as well as the many sites along the Freedom Trail. There are also many museums on the campuses of the world renowned universities in the city.

Is Chicago or Boston Better for Theater?

Chicago is an unbeatable place for theatre. Also, Boston is not as famous, but is still a good city to visit for its theatre productions.

Chicago is considered to be a world-class theater destination. 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.

While in town, many visitors enjoy seeing a show in Boston. The city has many historic, beautifully restored theaters where you can enjoy a show. Head to the theater district for some of the most famous venues.

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

Chicago is an unbeatable place for its local cuisine and restaurants. Also, Boston is not as famous, but is still a good city to visit for its restaurants.

Eat your way through Chicago, as it has many local or world renowned restaurants to choose from. 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.

Boston has a huge number of terrific restaurants. There are many local dishes that utilize fresh caught seafood and comfort food flavors. The cuisine also takes advantage of the city's Italian and Irish populations. Famous local foods include New England Clam Chowder, lobster rolls, and baked beans. You'll find hearty sandwiches and filling meals that warm your soul.

Is Chicago or Boston Better for Nightlife?

Chicago is an unbeatable place for nightlife. Also, Boston is not as famous, but is still a good city to visit for nightlife and partying.

The nightlife in Chicago is well established with world renowned clubs and venues. 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.

Boston has a lively atmosphere and nightlife is popular here. The city is known for its breweries, craft beer, and vibrant university neighborhoods. It also hosts regular outdoor movies and world class sporting events. The nightlife scene is varied, with some areas catering to the student population and other areas focused on the professional or sport-loving crowds.

Is Chicago or Boston Better for Music?

Chicago is an unbeatable place for live music. Also, Boston is not as famous, but is still a good city to visit for its live music scene.

Chicago is a world class music destination. The city is the birthplace of such interesting styles as modern gospel and the Chicago style blues.

The music scene in Boston is active and vibrant. Popular music venues include Lizard Lounge, Blue Hills Bank Pavilion, and The Middle East.

Is Chicago or Boston Better for Beaches?

Chicago is a good destination for its beaches. However, Boston is a mediocre city for the beache.

Chicago offers a nice beach destination. 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.

You can check out the beach in Boston. There are a few urban beaches in the greater Boston area that you can explore on a nice day.

Is Chicago or Boston Better for its Old Town?

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

The old town of Boston is one of the most recognized in the world. Boston is famous for its Freedom Trail, which takes visitors around the city's rich history. The oldest parts of the city are known as Boston Proper and include the neighborhoods of Beacon Hill, Historic Downtown, the North End, and the West End.

Chicago does not have a historic old town.

Is the Shopping Better in Chicago or Boston?

Chicago is an unbeatable place for shopping. Also, Boston is not as famous, but is still a good city 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 Boston. Head to Back Bay for some of the best high end shops. There are luxury brands and boutique venues that sell local art or crafts.

Is Chicago or Boston Better for Christmas?

The Christmas season is a nice time to visit both Chicago and Boston.

Visitors come from all around to experience the Christmas activities in Chicago. There's a number of seasonal celebrations, ice skating, and excellent shopping.

Boston is a very popular destination during Christmas. Christmas comes to life in the city with its Christmas Trees, holiday shows, and festivals.

Is Chicago or Boston Better for Christmas Markets?

Boston is a great destination for its Christmas markets. Also, Chicago is still popular, but not quite as popular for visiting Christmas markets.

Boston has a lively atmosphere around its Christmas markets. There are a number of European style Christmas markets that pop up during the holiday season around town.

Chicago has Christmas markets worth visiting. Shopping is a highlight of a trip to the city, and the Christkindlmarkt is not to be missed.

Is Chicago or Boston Better for Families?

You'll find first-rate kid-friendly activities in either Chicago or Boston.

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.

Boston is an amazing family-friendly city to visit. It's filled with history, but there are also many activities for kids who need a break from all of the historical stuff. Popular activities for all ages include the Museum of Science, the New England Aquarium, and exploring the waterfront, gardens, and parks around town.

Is Chicago or Boston Better for Couples?

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

Chicago is a good city for couples to visit. 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.

Boston is a nice destination for couples. Couples who enjoy history will enjoy exploring the city. Take a swan boat ride in the Public Garden and wander the unique route along the Freedom Trail. There are also many sporting and entertainment options around town.

Is Chicago or Boston Better for Backpackers and Budget Travelers?

Chicago and Boston are notable places to visit 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.

It's common for backpackers to visit Boston. Like most larger American cities, the city has a handful of hostels to choose from.

Is Chicago or Boston Better for Students?

Chicago and Boston are first-rate places to visit for 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.

Boston is a great destination for students. It is a city of students, with a number of world renowned universities located here including Harvard University, Boston College, and MIT. Many neighborhoods are filled with students and there are many student-centered activities around town including festivals and an active nightlife scene.

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

You'll find somewhat comparable public transit options in both Chicago and Boston.

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 in Boston is top-notch. There's the T, which is the subway, as well as a trolley, bus, and water transportation system.

Is Chicago or Boston a more walkable city?

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

Getting around Boston on foot is easy. The many parks and compact neighborhoods are best explored on foot.

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 Chicago Worth Visiting? and Is Boston Worth Visiting?.

Should I spend more time in Boston or Chicago?

How long in Chicago or Boston?

In either Chicago or Boston, you'll find plenty of activities to fill your time. In our opinion, Chicago has more to see and do, so we recommend that you spend more time in Chicago than Boston. However, 3-5 days is a good amount of time to spend in either destination.

Families should spend more time in Boston than Chicago. Because of the many family-friendly attractions and fun things to do for kids in Boston, it's a great place to visit with the whole family.

Couples should spend more time in Chicago than Boston. You'll find plenty of romantic sights and fun activities in Chicago that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Chicago than Boston 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 Chicago or Boston?

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.

In Boston, you'll find food and shopping. Most visitors spend time around the old town while in the area. One reason most visitors come is for the museums. 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 Chicago or Boston?

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.

In Boston, you'll find shopping and museums. The length of your trip often depends on your style of travel. Visiting the old town is also a must. One reason most visitors come is for the museums. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Five days in Chicago or Boston?

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.

Boston is a great place to explore. It is common to spend five days here. The old town is one of the main draws for visitors. Five days is a great amount of time to relax and see the many things that Boston has to offer. Anyone can find something fun to do here.

A week in Chicago or Boston?

Travelers enjoy the museums and theater when visiting the diverse 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.

It's hard to know how much time to spend in Boston. Many people enjoy the theater and nightlife when visiting Boston. One reason most visitors come is for the museums. 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.

For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, and The Best Historical Tours in United States of America.

When comparing the travel costs between Chicago and Boston, we can see that Chicago is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

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

Which is Bigger, Chicago or Boston?

Chicago has a larger population, and is about 5 times larger than the population of Boston. When comparing the sizes of Chicago and Boston, 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 Chicago or Boston?

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 Chicago or Boston in the Summer?

The summer attracts plenty of travelers to both Chicago and Boston. Many visitors come to Chicago in the summer for the beaches, the city activities, the music scene, and the family-friendly experiences. Furthermore, most visitors come to Boston for the beaches, the city activities, the music scene, and the family-friendly experiences during these months.

In the summer, Chicago is around the same temperature as Boston. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and Boston averages at about 73°F (23°C).

People are often attracted to the plentiful sunshine in Boston this time of the year. In Chicago, it's very sunny this time of the year. Chicago usually receives around the same amount of sunshine as Boston during summer. Chicago gets 326 hours of sunny skies, while Boston receives 304 hours of full sun in the summer.

Chicago gets a good bit of rain this time of year. In July, Chicago usually receives more rain than Boston. Chicago gets 3.9 inches (100 mm) of rain, while Boston receives 2.9 inches (74 mm) of rain each month for the summer.

Should I visit Chicago or Boston in the Autumn?

The autumn brings many poeple to Chicago as well as Boston. Most visitors come to Chicago for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area during these months. Additionally, the autumn months attract visitors to Boston because of the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In October, Chicago is generally around the same temperature as Boston. Daily temperatures in Chicago average around 56°F (14°C), and Boston fluctuates around 54°F (12°C).

In the autumn, Chicago often gets around the same amount of sunshine as Boston. Chicago gets 195 hours of sunny skies this time of year, while Boston receives 194 hours of full sun.

Chicago usually gets less rain in October than Boston. Chicago gets 2.2 inches (56 mm) of rain, while Boston receives 3.3 inches (84 mm) of rain this time of the year.

Should I visit Chicago or Boston in the Winter?

Both Boston and Chicago are popular destinations to visit in the winter with plenty of activities. The winter months attract visitors to Chicago because of the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine. Also, the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Boston this time of year.

It's quite cold in Boston in the winter. The weather in Chicago can be very cold. Chicago is much colder than Boston in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and Boston fluctuates around 29°F (-2°C).

Chicago usually receives less sunshine than Boston during winter. Chicago gets 134 hours of sunny skies, while Boston receives 153 hours of full sun in the winter.

In January, Chicago usually receives less rain than Boston. Chicago gets 1.9 inches (47 mm) of rain, while Boston receives 3.4 inches (87 mm) of rain each month for the winter.

Should I visit Chicago or Boston in the Spring?

Both Boston and Chicago during the spring are popular places to visit. The beaches, the activities around the city, and the natural beauty are the main draw to Chicago this time of year. Also, many travelers come to Boston for the beaches, the activities around the city, and the natural beauty.

In the spring, Chicago is a little warmer than Boston. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and Boston averages at about 48°F (9°C).

In Boston, it's very sunny this time of the year. It's quite sunny in Chicago. In the spring, Chicago often gets around the same amount of sunshine as Boston. Chicago gets 218 hours of sunny skies this time of year, while Boston receives 225 hours of full sun.

It rains a lot this time of the year in Chicago. Chicago usually gets more rain in April than Boston. Chicago gets 4.3 inches (108 mm) of rain, while Boston receives 3.5 inches (89 mm) of rain this time of the year.

Typical Weather for Boston and Chicago