Chicago vs. Boston

When it comes to the showdown between Chicago and Boston, the rivalry runs deep. Each city has a unique flavor and character that can't be found anywhere else. From deliciously toe-curling dishes to histories that run deep, these two US destinations are special in their own right. So which one is better? The answer may come as a surprise - it depends on what you're looking for! 
Chicago vs. Boston

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If you prefer a fun-filled vacation with each day brimming with a different vibe and energy, Chicago is made for you. The Windy City is a melting pot of adventure, from its heartwarming theater scenes to the most wonderful musical escapades.

Boston, on the other hand, can offer you entirely different experiences. The capital of Massachusetts is for tourists who want to enjoy a quieter pace of life, perhaps a peaceful escape. Here, you can walk through many historical sites and enjoy rows of seafood and chowder with gusto!

So, who wins in the great debate between Chicago vs. Boston? It’s impossible to say for sure – both cities exude undeniable charisma. Whichever one you choose, you’re sure to cross many firsts on your bucket list. And if you have the means, why not visit both to get the best of both worlds?


If you’re looking for a getaway spot that has everything, Chicago should be at the top of your list. It will show you how worthy it is to be called the ‘Best Big City to Visit in the US’, a title bestowed by Condé Nast Traveler. The most surprising thing? This spot in Illinois has been the titleholder for this particular achievement for six consecutive years!

This means that the Windy City being dubbed the greatest metropolis to drop by in the whole United States of America is no coincidence. It’s a worthy vacation spot that has achieved a wonderful feat: perfecting the art of becoming a world-class destination.

Want to enjoy the most beautiful cityscapes and then go on an intimate trip in nature the next day? How about enjoying most of your vacation lounging in the sand and listening to the tranquil waves? Maybe you’re more into the clubbing scene, with more than a dash of alcohol and some of the greatest music to ever exist. Truly, you’ll find no matter what it is you’re craving in Chicago!

What Makes Chicago Unique?

The Most Cerulean Waters Outside the Caribbean

There’s only one thing to do once you get off your vehicle and witness Chicago in all its glory: marvel and sigh in wonder at the view. Yes, there’s the beautiful skyline and the city’s breathtaking nature spots. However, it’s the Windy City’s phenomenal beaches that will make you fall in love over and over again. The best way to describe them, you ask? Like a picturesque scene straight out of a postcard!

In fact, you may consider Chicago the possessor of the most cerulean waters outside of the Caribbean. There’s no color more fitting than blue for this city; it’s as if the place is tailor-made for it. Not only is it because it’s the holder of the shiny title ‘The Third Blues Capital of the Planet’. This spot can also boast tranquil beaches that sparkle whenever the waves kiss the shore.

These shiny, soothing waters serve as an oasis for tourists and locals alike, and nothing beats experiencing them in the flesh! Pair these works of nature with the Windy City’s stunning sunsets and laid-back locals, and you’re in for a seaside trip that’s truly out of this world.

You can explore to your heart’s content, discover the unique ecosystem, and take a boat tour to get up close and personal with the loveliest scenery.

To give you a clue on where to start your fun under Chicago’s sun, why not drop by North Avenue Beach? It has no shortage of wonderful entertainment, whether you’re looking for an exciting night out or a relaxing day lounging in the sand. There’s also the Windy City’s Loyola Beach, a wonderful waterfront that can make your family’s bond tighter than ever! Here, you can enjoy Lake Michigan’s cerulean views and feast on many breathtaking cityscapes.

And if you’re eager to spend quality beach time with your furry companion, Montrose Beach will welcome you. It’s one of the official dog beaches in Chicago, which means your canine can freely frolic on the beach and chase the waves for countless hours. Know that it’s also the largest beach in the Windy City, so you won’t get bored anytime soon!

For Those With a Heart for Thespian Pursuits

Do you find joy in watching people wear flashy clothes and colorful costumes? Maybe you’re fascinated by the actors and their fluid skills in changing faces and demeanors. Or do you dream of going center stage one day, with the spotlight following your every move as you act your heart out in front of hundreds? No matter which it is, you will definitely enjoy Chicago!

It’s a haven for people who enjoy thespian pursuits; for those with a taste for the finer things in life. In fact, no visit to the Windy City is complete without dropping by the theaters! There are about 200 companies, both small and big-time, that offer shows of varying specialties. These vary from award-winning ones like The Sound of Music to innovative works made by local playwrights.

Craving for a fun night without spending a dime on booze? Then Chicago’s many sketch comedy theaters got your back. And if you want to bask in the classics, such as the Devil Wears Prada and To Kill a Mockingbird, then you’re more than welcome! In this city, you can unleash your inner drama royalty by going to intimate black box spaces or Broadway-style venues.

Truly, the Windy City is home to many unique theater experiences and troupes that can show you everything you’ve ever imagined. You can check out some of them below, but remember, nothing beats watching them perform live:

  • Lookingglass Theater Company. If you’re a fan of the classics, then you’d enjoy this troupe’s performances down to your very bones. Here, get ready to go down the rabbit hole into the wonderland of drama and watch Lookingglass Alice, Arabian Nights, and many more!
  • The Black Ensemble Theater. Craving for theater plays that provide you with more than just laughs and entertainment? Then you’d enjoy visiting this troupe known for being the African American and mainstream arts community leader! Not only do they perform well, but they also act out every scene with a burning drive to destroy racism once and for all.

Gotham City in Real Life

If you’re a huge fan of superheroes, particularly one that fights crime and villains in a bat-themed suit, you’d go loco over Chicago. It’s the inspiration for Batman’s main place of operations, the wonderful Gotham City! Few can boast of dropping by a model for a science-fiction world seen in movies and comic books, so you’d hit the jackpot if you visit this spot in Illinois.

Of course, you may think they look different on the surface. After all, one’s a genuine bustling US City, while the other is a fictional metropolis with villains running rampant 24/7. However, this will change once you get to know Chicago in all its splendor. In this real-life Batman setting, you’ll fuel your imagination to the utmost limit!

Like Gotham, the Windy City is home to some of the most phenomenal structures in the world. The former has towering skyscrapers and monuments, including the Arkham Asylum and Wayne Manor. Meanwhile, Chicago can boast of the Willis Tower, John Hancock Building, and the Aqua Tower (to mention a few!). You may find yourself replaying scenes while on the streets, maybe even start reminiscing about the Joker and Batman’s moments.

Want some bits on which Chicago buildings specifically made it into the Batman series? Check out the list below to satiate your curiosity and give you an idea of which places in the Windy City will catch your eye.

  • Chicago Board of Trade Building. If you’re a die-hard Batman fan, you’ll know which Gotham structure was influenced by this structure. It served as a model for the Gotham City Police Department; in fact, it was featured in The Batman movie. A quick glimpse will have you jumping in excitement, especially since it’s also considered the pinnacle of Art Deco designs.
  • The Jewelers Building. Familiar with the classic grandfather time clock scenes in many superhero series? The Jewelers Building is right up your alley, especially once you witness the 5 ft. (1.52 m) Father Time statue at the top. To elaborate, this structure has been featured in the 2005 Batman Begins, so bring your camera and take plenty of shots!

If you ever find yourself wishing that Gotham City was real, take heart. Chicago is just as cool – and you don’t even have to worry about a supervillain showing up to wreak havoc. All you need to do is put on your cape and experience the Windy City’s comic-like grandeur!

The Third Blues Capital of the World

Where should humans who feel blue and people who love the blues go to? Chicago, no doubt! It’s known for being the third blues capital of the globe, and you know what they say about music – it’s the best remedy for the soul! That’s why choosing the Windy City for your vacation is like hitting two birds with one stone. You get to boost your mood while listening to some of the greatest performances ever.

It’s the best pick-me-up activity for those feeling under the weather and for tourists who identify as melomaniacs. Of course, even if you don’t fall into either category, you’ll still enjoy this mecca for blues music! Who wouldn’t, when every beat of this sound tells a story that tickles your heart?

If you’re wondering how a series of beats and lyrics can stir up the hidden depths of your being, the answer is simple. Chicago has long perfected the art of the blues, which came around in the city around the 1920s. In fact, the Windy City and its talented artists became so enamored with blues music that they developed their version of it in the 1950s.

Originally, the music was made using lead acoustic guitars, but Chicago bands created their own version. Electric guitars became their go-to instrument, with the support of harmonica, piano, drums, and bass. The result? The Windy City gave birth to a new sound known all over the planet as Chicago Blues!

You’d enjoy this fluid, jazz-like blues music with its own identity, especially if you pay attention to the lyrics. It’s like listening to a story in song form – with varying plots depicting different life sceneries. One moment, you’ll hear the singer describe their electrifying city life. The next, they’ll serenade you with some of their most passionate adventures.


If there’s something you should learn about Boston, it’s this: it will satiate any hunger you’re feeling! It’s a tourist’s perfect paradise, armed to the core with every kind of entertainment you could think of. Craving for an adventure of a lifetime or a simple weekend getaway filled with culture and history? Then no doubt, “Beantown” is made for you.

Here, you can take a literal trip down memory lane without needing a time-turner. Boston has so much to offer, especially when you want to know more about the days of old. It provides so much history that its streets even bleed memories of times long gone.

If this is not your cup of tea, fret not. Beantown is more than just the Freedom Trail and its incredible landmarks. In this city, you can drown in the tastiest seafood dishes and get lost in the many museums made for different interests.

What Makes Boston Unique?

Shrimply the Best Oysters, Lobsters, and Clams

Some people are addicted to desserts, enamored by the sweet, creamy goodness these treats provide. Others can’t get enough of the meat’s juiciness, with each bite being more tantalizing than the last. In Boston, though? Well, locals are obsessed with whipping out one of the greatest gifts the sea has to offer – seafood.

That’s right, if you’re looking for seafood that’s as fresh, salty, and delicious as the waters of the Atlantic, then Beantown is the place to be! The main city of Massachusetts ain’t playing when it comes to the fruits of the sea; it’s known as America’s seafood capital. With its rich maritime history and proximity to the sea, it’s no surprise that it’s home to a wide variety of fresh and delicious catches.

From local favorites like clam chowder and lobster rolls to oysters and scallops, the city has something for every seafood lover. Maybe you prefer to keep the cooking simple, like having boiled clams for dinner? Or, you’re leaning towards having a waterfront feast of fried fish sandwiches and crab cakes. Whatever it is you’re hungry for, Beantown and its reputation as a seafood wonderland will never fail you!

Of course, there’s no better way to experience Boston seafood than by visiting the city’s many reputable restaurants. You can never go wrong with the Neptune Oyster, famed for its freshly shucked oysters and scallops ceviche. There’s also Holly Crab, an Allston spot that serves seafood in Cajun style.

If you’re feeling adventurous, why not try Yakitori Zai and get a sample of their lobster spaghetti? It’s the perfect combination of seafood and Italian cuisine, with flavors enough to make your mouth water. Don’t forget to drop by Quincy Market, a historical spot that offers a one-of-a-kind seafood experience in Boston! As a bonus, this spot has the perfect backdrop while you enjoy your gastronomic fantasies!

Where the Past and Present Meet

If there’s a city that can best be described as the crossroads of the past and present, it’s Boston. It’s the perfect example of a paradox, merging old-world roads with contemporary architecture. Traveling down its streets is like walking down decades-old avenues, all while living your life out in the present!

Not many metropolises can boast about this feat, which means a trip to Beantown is in itself an experience on a whole other level. After all, hardly any city can build towering skyscrapers around some of the oldest relics from a distant past. An obvious example of this achievement, you ask?

Well, check out Boston’s eclectic combination of classic gothic churches and glass buildings that touch the sky! There are also plenty of decades-old statues around the city, so well-preserved that you’d think they’d been made yesterday. Don’t forget the many buildings of ages long passed, like the Old State House that date way back to 1713. It’s surrounded by modern structures, making lovely scenery that can be considered starkly different.

That’s not all, though. Perhaps the most evident proof of this city being a wonderful paradox is the Freedom Trail. It’s a walking path that takes you to the metropolis’ most important landmarks, maybe even transport you to Boston’s rich past. The cherry on top? The trail doesn’t go off the urban road; instead, it passes all over the city!

The Freedom Trail is a painted yellow line leading to 16 historical sites. These spots are where the most significant events occurred, which led to Boston being dubbed the ‘Cradle of Modern America’. This means that following this road is a lot like retracing the footsteps that made USA’s independence possible.

Some landmarks you shouldn’t miss when following this 4 km (2.5 mi) path include the Boston Common, Paul Revere House, and the Boston Massacre Site. There’s plenty more to look forward to, so remember to take the time to follow the trail of revolutionary heroes!

It’s Always the Right Time for Festivals

Boston is truly a city to be reckoned with – after all, it’s America’s City of Firsts! It’s the birthplace of the USA’s independence and a major powerhouse in the launch of higher education. On top of that, the city is known for its well-preserved heritage, which makes a wonderful contrast to its constant innovation. However, they are just appetizers to the exciting things Beantown can offer.

What most people don’t know is that it also hosts the most phenomenal festivals in Massachusetts, maybe in all of New England! In fact, you may even think that the city celebrates every kind of occasion, be it an event with traditional music or one filled with loud fireworks. From food to film festivals, music concerts to movie screenings – it’s all here in Boston.

These celebrations are a great change of pace and scenery, especially if your main aim for vacation is to unwind. You shouldn’t miss it if you’re eager to explore more of the globe and have genuine human encounters. Imagine attending some of the greatest events in the world with some of the best people; it’s an experience worth noting in your life book!

Keen on attending the most electrifying events in Beantown? You may want to start with the classic, the famous Harborfest Festival! It’s a five-day celebration during the first week of July, considered the biggest 4th of July event in America. Look forward to the Pops Fireworks Spectacular and the illuminations sure to light up the sky.

Boston also has something up its sleeves for the artists and aesthetes, so rejoice if you’re one. One great example would be the Mystic River Celebration which lasts a whopping thirty days! You can also whip up a fun costume during the Frog Pond Pumpkin Float, an event exclusive during Halloween. Or, why not attend the Boston Book Festival, which, you guessed it, is made for bookworms?

Plenty more of these thrilling events can be experienced in Boston, making it one awesome getaway destination.

A Place to Get Lost and Be Found

What’s a place you can get lost in and find yourself at the same time? There’s no doubt about it; it’s the museums! These magical hubs of culture will take you back in time and have you experiencing ages long passed. It’s also where you can get to know yourself better and find out about interests you’ve never considered before.

And, of course, expect Boston, one of the oldest cities in America, to have only the best and the most interesting museums around! This city is the perfect destination if you feel like you don’t have a place in the world or are looking to get to know yourself better. It has many fascinating exhibits and artifacts spread throughout the vicinity, and viewing them can help you in your journey.

Whether it’s through history or culture, its galleries feature something that speaks directly to your soul. The city can boast of its science museums, filled with interactive exhibits and IMAX productions. There are also art exhibits everywhere, perfect if you’re an aesthete or an artist looking for your next inspiration!

Interested in uncovering the many wonders Boston’s museums hide? Well, here’s a look at some of the best ones that will blow your mind:

  • Isabella Stewart Gardner Museum. If you’re looking for a museum with the perfect mix of culture and grandeur, then this spot won’t disappoint you. It has a Venetian-inspired palazzo, with plenty of luxurious architectural pieces. It’s also filled with the works of Botticelli and Titian, as well as thousands of relics from around the globe.
  • Museum of Science. Going to this museum during vacation is more than for the aesthetics – you’ll surely emerge a smarter human afterward! There are plenty of interactive experiences that will shower you with knowledge, as well as modern displays and IMAX movies. Tip: the museum is also home to a big gift shop that may contain the souvenirs and snacks you’re looking for.

Which Is a Better City – Boston or Chicago?

Boston vs. Chicago – choosing between these US cities is like deciding between two of the brightest stars in the sky. Both are armed with charisma that makes tourists want to drop by over and over again. They’re brimming with many magnificent sights, attractions, and unique experiences for travelers. However, if you have to pick which one to visit, there’s no other way than to consider your preferences.

Boston is made for those who want to get lost in a city of culture and history. Here, you can walk the red brick road of times long past and witness the ways of revolutionary heroes. On top of this, get your tastebuds ready for a vacation that’ll give you the best and freshest seafood ever!

Meanwhile, Chicago can offer you a night out that you’ll remember for the rest of your life. The city only has the best alcohol in stock, on top of providing top-tier entertainment. If you’re a huge fan of theater and music performances, this spot in Illinois is made for you.


Is Boston Safer Than Chicago?

Based on Numbeo’s analysis, Boston is safer than Chicago. It’s a more secure destination with a safety scale rating of 60.74, compared to the Windy City’s 34.02 mark. It doesn’t matter if you’re walking around Boston at night or during broad daylight; you’ll still be safe and sound.

You can’t say the same with Chicago, though, especially when it’s dark. In fact, ratings show that the crime level in this city reaches a whopping 65.98. Chances of theft and assault are high, so it’s best to be vigilant when dropping by this area in Illinois. Meanwhile, the crime index in Boston shows a surprisingly low grade of 39.26.

Is Chicago Cheaper or More Expensive Than Boston?

If you’re on a budget and torn between Chicago and Boston, choose the former. This is because, according to Living Cost, the Windy City is 22% less expensive than Beantown. It occupies the 156th spot in the rankings of the most costly in the USA, while Boston got the 27th place.

This means you enjoy your vacation in Chicago more without worrying about spending outside your price range. To give you a brief breakdown of expenses, a simple fast-food meal in the Windy City costs only $8.75. In Beantown, you get the same, but you have to pay a whopping $10. Similarly, a beer in a downtown pub in Chicago is worth $5.37, while in Boston, it’s going to be $7.02.

Boston vs. Chicago Weather

When it comes to weather, Beantown has a much better situation than Chicago. True, both cities belong on the roster of the USA’s wintry towns, which means they’re not unfamiliar with freezing temperatures and snow. However, Boston still has many warm days compared to the Windy City.

To elaborate better, there are about 200 sunny days in Boston every year, with the summer season reaching 82.4°F (28°C) at its peak. Meanwhile, Chicago only has 189 sunny days per year, with the hot season only reaching up to 83.9°F (28.8°C).

Boston gets the stick with having much heavier snowfall, though. Beantown has an average of 48.1 inches (1221 mm) of snow yearly, while the Windy City only has 35.1 inches (891.5 mm).

Is Chicago Colder Than Boston?

Generally, Chicago is a much colder city than Boston. In fact, the average temperature in the Windy City ranges from 22°F (-5.56°C) to 83°F (28.33°C). During the peak of the winter season, the average daily temperature gets below 43°F ( 6.11°C).

Meanwhile, Boston can also get pretty chilly, but not as much as Chicago. The average yearly temperature can vary from 23°F (-5°C) to 82°F (27.78°C). During the winter, the daily temperature can reach 45°F (7.22°C).

Both cities have January as their coldest winter month. However, Chicago still takes the cake for having a chillier temperature during this time, ranging from 22°F (-5.56°C) to 33°F (0.56°C). Meanwhile, Boston gets about 24°F ( -4.44°C)to 37°F ( 2.778°C).

Boston vs. Chicago in Winter

Boston and Chicago are equally great winter destinations, making it hard to choose between them. However, if you’re eager to decide which city will host your getaway, check your trip expectations.

Boston has less extreme winter, but expect the snow to last for longer than in the Windy City. Here, you can enjoy plenty of seasonal activities, from skiing and sledding to ice skating with your loved ones. However, you can also walk the Freedom Trail during this season and see sceneries you’ve never witnessed. Plus, Beantown’s hot chocolate is to die for, particularly the one at L.A. Burdick Chocolates.

Meanwhile, the Windy City has an extremely cold season, but the streets are alive and never empty. You’re free to roam the avenues and attend the many operas and concerts in a pub or on the road. There are also Christmas markets to look forward to, like the one at Daley Plaza and Wrigleyville. Don’t forget the many skyscrapers you can use at a vantage point to admire the Windy City as a whole – it’s a genuine winter wonderland full of activities.

Chicago vs. Boston Accent

Boston and Chicago may have plenty of similarities, but their respective accents are not one of them. They’re in entirely different leagues, with the Windy City having the least distinct accent in the USA. On the other hand, Beantown is the thickest accent of all, as stated by CBS Chicago.

To further elaborate, Chicago’s accent is known for using “th” over “d” sounds. Locals also tend to pronounce their vowels longer, sometimes even voicing out “o” sounds into “a” instead. They also use “r” harder, even more so than the General American accent. In addition, Chicagoans are fond of nasalization throughout their speech, mainly in words with “n” and “m”.

On the other hand, Boston’s accent has different ways of pronouncing “r” sounds. Sometimes, it becomes “ah” and “aw”; it can even turn into “ah”, replacing the “r” in particular words. For instance, “daughter” becomes “daughtah”. Locals in Beantown also tend to drop consonants and combine words, which occurs when they speak too fast.