But size isn’t everything. Boston and Chicago also differ in many other key areas, and each city has its own list of advantages and reasons to visit. Boston, for example, is famous for its rich history, having been founded back in 1630 as one of the original colonies. Chicago, meanwhile, is beloved for its bars, breweries, and entertainment, with awesome theater and comedy shows.

In this guide, we’ll dig into all the big differences that separate Boston and Chicago. We’ll look at their main attractions and activities, their nightlife and food scenes, what kind of entertainment you can enjoy in each city, and even how much it costs to visit them. By the end, you should have a much clearer picture of which city is best for you. So, let’s get started!

Contents:

• A Quick Overview Of Chicago vs Boston
• Which Has The Best Weather?
• Which Is Best For Activities?
• Which Is Best For Nightlife?
• Which Is Best For Live Entertainment?
• Which Is Best For Shopping?
• Which Is Best For Food?
• Which Is Best For Families?
• Which Is Best For Couples?
• Which Is Best For Backpackers?
• Which Is Cheapest?
• Where To Stay According To Your Budget
• Chicago vs Boston: Which Is Better?

Wandering Our World’s Ten-Second Comparison:

A Quick Overview Of Chicago vs Boston

Chicago: A Quick Overview

Chicago is the biggest city in the state of Illinois, as well as being the third-largest city in the U.S. today, ranking only behind New York and Los Angeles. It’s by far the biggest city in the Midwest region, with a population of around 2.7 million people and over 9.6 million in the surrounding Chicago metropolitan area.

The first settlement in the area was established in 1780, though Chicago wasn’t officially incorporated as a town until 1833. Thanks to its handy location on the shores of Lake Michigan, it experienced rapid growth, becoming a city in 1837. Even the Great Chicago Fire of 1871, which left 100,000 people homeless, barely slowed the city’s rapid expansion.

The city was the site of the world’s first steel-frame skyscraper, and has developed into a leading hub for finance, industry, technology, and culture, as well as boasting one of the busiest airports worldwide – Chicago O’Hare. Along with its thriving economy, the city is renowned for its exciting arts scene, contributing much to the world’s of music and comedy, in particular.

From a touristic standpoint, Chicago is a thrilling city to visit. Bustling, buzzing, and dynamic, it’s a sprawling, cinematic metropolis, filled with impressive architecture and a dizzying array of museums. Chicago is also known as a food and drink capital, attracting some of the country’s leading chefs, while also boasting more breweries than any other city in the U.S.

Boston: A Quick Overview

Boston is the state capital and the most populous city in the Commonwealth of Massachusetts. It’s also the largest city in the whole of New England, as well as the main cultural and financial center for the region. The total population here is around 650,000, with over 4.9 million in the full metropolitan area.

As one of the oldest cities in the U.S., Boston’s history goes back much further than Chicago’s. It was founded in 1630 by English settlers, and it notably played a key role in many major historical events, especially during the American Revolution, like the Boston Massacre and Boston Tea Party.

Even after the Revolution was over and the Declaration of Independence had been signed, Boston continued to be a significant and influential city, leading the way in fields like education, research, law, medicine, and business. Today, it’s home to thousands of startups, making it one of the most forward-thinking and innovative cities in the U.S.

Naturally, as the site of so much history, Boston is also a major touristic destination, drawing in tens of millions of visitors each year. Many people are eager to visit iconic local landmarks like Faneuil Hall or explore world-famous college campuses. The city is also known for its delicious food, like Boston Cream Pie and lobster rolls, along with its quirky neighborhoods.

Which Has The Best Weather?

Let’s start off with a look at the weather in both cities. This is one of the areas in which the two are really similar. In fact, conditions in Chicago and Boston are almost identical for large parts of the year, with warm summers, cold winters, and similar levels of rainfall. The only big differences are that Boston gets more snow and Chicago has stronger wind.

Which Is Best For Activities?

Despite being quite different locations in a lot of ways, Chicago and Boston both offer long lists of interesting landmarks to see and fun activities to enjoy. You can easily spend several days in each city, experiencing something new and different each day. Let’s take a look at the best things to do in both locations to see how they compare.

Chicago: The Activities

Chicago is famed for its many landmarks and impressive architecture. Therefore, most visitors will want to start off by seeing the big sights, like Cloud Gate – affectionately known as “The Bean,” this stunning public structure is made up of 168 stainless steel plates, with a polished, reflective surface, making it look like something that landed from an alien planet.

Cloud Gate sits in Millennium Park, a 25-acre space featuring art installations and sculptures, along with impressive views of the surrounding cityscape. The city also has other excellent parks and green spaces, like Grant Park, where you’ll also find attractions like Shedd Aquarium and the Art Institute of Chicago – home of one of the most impressive art collections in America.

Other great places to walk and soak up the city’s vibes include the Magnificent Mile – Chicago’s leading shopping district with major department stores like Bloomingdale’s and Macy’s – and Navy Pier, where you can enjoy family attractions, like rides and a Ferris wheel, or gaze out across the shimmering waters of Lake Michigan.

Adventurous visitors might even like to take to the water on a speedboat or kayak, or check out the hiking trails dotted across the city, like the 18.5-mile Lakefront Trail. Other things to do include visiting The Field Museum, one of the world’s best natural history museums; Wrigley Field, home of the legendary Chicago Cubs; and the iconic Second City comedy theater.

Boston: The Activities

Arguably the biggest draw of Boston is its rich history, and visitors to this city will surely want to check out its oldest and most significant landmarks. Fortunately, the Freedom Trail makes it easy to see all the big sights with ease. This 2.5-mile trail passes by 16 colonial and revolutionary locations, like Boston Common and the Paul Revere House.

Other must-see Boston landmarks include Faneuil Hall, where iconic historic figures like Samuel Adams once gave rousing speeches in the push for independence, and the USS Constitution, the oldest naval warship to still be afloat today, having first launched in 1797. You can also take tours of famous college campuses in Boston, like Harvard and MIT.

For a deeper dive into history and culture, visitors might want to visit some of Boston’s many museums, which offer diverse exhibits and displays. The MFA, for example, has a colossal collection of more than 450,000 artworks, while the Museum of Science explores the wonders of our world and the Boston Children’s Museum is a great place to spend some time as a family.

Boston also has nice walking paths, just like Chicago, such as the Esplanade, as well as opportunities to visit local beaches or get out on the water. There’s an iconic sports stadium here, too – Fenway Park – along with cool neighborhoods beyond the historic center, like trendy South Boston, Italian-themed North End, and colorful Chinatown.

Overall, both cities are filled with interesting attractions and activities, but the differences are clear to see. There’s a bit more going on in Chicago, with a wider range of museums, galleries, and theaters. Boston, meanwhile, is the premier destination for history buffs, while also offering fun coastal activities, like boat trips to nearby harbor islands or even whale-watching tours.

Which Is Best For Nightlife?

Both Boston and Chicago have more than enough activities to keep you busy during the daytime. But how about the evenings? Well, fortunately for nightlife lovers, these cities are also very active and energetic in the evenings, with plenty of thumping clubs and fun bars just waiting to welcome you in.

Chicago’s nightlife scene is one of the best in the U.S. right now. It has world-famous clubs where you can dance the night away, as well as lots of super live music spots to listen to jazz, blues, and more. Plus, with Chicago boasting more breweries than any other major city, it’s a haven for beer drinkers.

Boston also feels lively and exciting after dark, with some great craft breweries, bars, and seafront pubs of its own. The nightlife scene here is also quite diverse, with some areas offering student-friendly dance clubs and other places being filled up with laid-back sports bars or fancy rooftop restaurants.

Overall, when it comes to nightlife, Boston’s not bad, but Chicago wins this battle hands down. It’s simply one of the best cities in the country to spend an evening.

Which Is Best For Live Entertainment?

Live entertainment is a massive part of Chicago culture. This city was the birthplace of many musical movements in genres like blues and gospel, and it’s also home to the best-known improv theater troupe of all: Second City. And if that’s not enough, it also has a fantastic theater scene, second only to Broadway in terms of number and variety of shows on offer.

Whether you want to laugh, cry, or marvel at musical talent, you can do it all here. There are amazing venues scattered across the city’s downtown districts, like jazz clubs, cultural centers, rock ‘n’ roll clubs, wineries, theaters, and even opera halls. The city also has several professional sports teams, most notably the Cubs, White Sox, and Bulls.

Boston is also a big sporting city. Visitors might like to catch a ball game at Fenway Park and see the famous Red Sox play, or check out one of the city’s other top teams, like the Celtics, Bruins, and Patriots. There are also some pleasant theaters and live music spots across Boston, but it’s not got the same level of live entertainment as Chicago.

Overall, for most kinds of live entertainment, the Windy City is the clear winner. For sport, it’s a slightly different story. Both of these cities are sporting havens in their own right, and the best one for you will really depend on which team (or stadium) you want to see the most.

Which Is Best For Shopping?

Shopping is always a fun activity in any big city, and it’s particularly enjoyable in Chicago. There, shopaholics can enjoy the amazing “Magnificent Mile,” filled to bursting point with upscale boutiques and high-end fashion brands, as well as lots of major department stores that can keep you busy for hours on end as you search for the perfect souvenir to take back home.

For something more affordable, Chicago’s Woodfield Mall offers close to 300 stores, and Andersonville is a quirky neighborhood with a range of Scandi furniture stores and independent antique shops. You’ll also find great specialty shops along State Street, along with discounted attire at the Fashion Outlets of Chicago complex.

Boston is a terrific shopping destination, too. For posh stores and deluxe brands, head to Newbury Street. For everything else, try City Centre Crossing. North End is also a top spot to explore specialty stores and indie boutiques with bargain prices, while Quincy Market offers over 100 stores in a beautiful historic building.

Overall, Chicago stands out as the better shopping destination, with a much wider range of stores and things to buy.

Which Is Best For Food?

One of the very best things about visiting either Chicago or Boston is sampling the local food. Both cities have their specialties, and it’s almost impossible to decide which one is better than the other, as it’s all, quite literally, a matter of taste!

With its prime coastal location, Boston has some of the finest seafood in America. The lobster rolls here are out-of-this-world, and other popular dishes include clam chowder and oysters. Of course, if you don’t like seafood, you’ll still find plenty to eat, with some super sandwich shops, ramen bars, burger joints, and pizzerias. Got a sweet tooth? Try some Boston cream pie.

Chicago, meanwhile, is one of the pizza capitals of the world. Famed for its deep dish delights, it’s a comfort food paradise. You’ll also find world-beating hot dogs here, covered in mustard, relish, and more, as well as Italian beef and sweet treats, like the Rainbow Cone. Plus, as mentioned earlier on, Chicago has an amazing bar and brewery scene.

Overall, the best city for you will depend on what kind of food you love most. Naturally, seafood addicts will adore Boston, but there are few foods quite as indulgent as Chicago’s hot dogs and pizzas. Chicago’s scene is also a little more diverse, with everything from casual street foods to gourmet Michelin star meals.

Which Is Best For Families?

If you’re planning a family vacation, it can be tricky to choose between Chicago and Boston. Both cities are appealing and welcoming to families with kids of various ages. So, which one should you pick?

Well, if you’re looking for the biggest and best range of family activities, head to Chicago. There, you’ll find a long list of attractions, ranging from zoos like Lincoln Park and Brookfield to the Navy Pier fairground rides and Shedd Aquarium. There are also multiple museums catering to younger visitors, like the sensory Sloomoo Institute and fun-filled Chicago Children’s Museum.

Over in Boston, meanwhile, the main attractions tend to be oriented around history. So, if your kids are eager to learn about America’s past, this is a great place to go. You can walk along the Freedom Trail, roam around Boston Common, or head to Boston Children’s Museum. Boston also has a Legoland, as well as pleasant parks and green spaces for picnics and play.

Overall, both cities are equally impressive for families, with plenty of ways to fill your days. Boston is naturally more appealing for history-loving families, but Chicago has the wider range of traditional attractions.

Which Is Best For Couples?

You might also consider a couple’s getaway to either Chicago or Boston. But which of the cities is the most romantic and best-suited for lovebirds?

Well, Chicago can be a thrilling city to see with someone special. There’s lots of live entertainment here, like theater shows, comedy, and music, perfect for couples who plan on staying out late and making the most of every moment. The food is also fantastic, and couples can also shop till they drop in places like the Magnificent Mile.

Boston is quieter and arguably a little more romantic, with its European-style vibes and decorative, historic architecture. It’s great for couples who share a passion for history, with lots of nice parks and gardens you can roam around with your partner. On the downside, there’s not quite as much to do here as in Chicago.

Overall, Chicago is slightly better for most couples, thanks to its more dynamic vibes and exciting entertainment. However, older couples or those looking for a more relaxing break may prefer Boston.

Which Is Best For Backpackers?

Backpackers might also like to stop off at Chicago or Boston to take in the sights and soak up some of the local culture. Both cities have cheap hostels where you can stay and mingle with other travelers, but which is best?

Well, you’ll definitely find a wider range and greater number of hostels in Chicago. In spite of its size, the city is also quite easy to get around, with public transport services operating round-the-clock to take you almost anywhere you want. There are lots of museums and other places to visit, as well as surrounding state parks for outdoor recreation.

Boston isn’t quite as backpacker-friendly, with slightly higher prices and fewer places to stay. With that said, it’s still a fantastic city to explore, especially if you’re interested in history and want to see famous locations like Faneuil Hall in person. Plus, there’s a big student population here, so it’s a top spot for young travelers to mix and mingle.

Overall, backpackers will probably find a little more to fill up their itineraries in Chicago, especially at night, with all the shows, bars, and clubs. But you can still have a fun backpacking expedition in Boston.

Which Is Cheapest?

When it comes to cost, there’s not a massive difference between Chicago and Boston. Both cities have similar rates when it comes to things like accommodation and food, and the total cost of your trip will ultimately depend on what kinds of activities you want to enjoy and what sort of hotel you decide to stay at.

With that said, there are a couple of additional factors to take into consideration. Due to its larger size, you may spend a little more getting around in Chicago. However, the vastness of this city also gives you more options in terms of food, drinks, and accommodation, so you might find it slightly easier to stretch your budget, if you plan ahead.

Both cities also have free activities, like music festivals during the summer. Almost all of Chicago’s museums have free visit days each week, and there are even free family attractions in the Windy City, too, like Lincoln Park Zoo. In comparison, Boston also has free museum days and fee-less parks, but not quite as many freebies as Chicago.

Where To Stay According To Your Budget

Chicago

Budget: Perched in the heart of Chicago, citizenM Downtown captivates with its sleek, modern design and panoramic city views. The lobby’s vibrant ambiance welcomes guests to an oasis of contemporary elegance. Luxurious furnishings, floor-to-ceiling windows, and thoughtfully curated artwork create a captivating urban retreat, inviting guests to indulge in refined comfort.

Luxury: Elevating Chicago’s skyline, The St. Regis Chicago exudes timeless elegance and sophistication. Towering above the city, its sleek architecture commands attention, while luxurious interiors offer unrivaled opulence. From the grand lobby adorned with exquisite art to the breathtaking views from lavish suites, every detail exudes unparalleled beauty.

Boston

Budget: Radiating historic charm and modern luxury, Hilton Boston Park Plaza enchants with its timeless elegance. From the grandeur of its restored lobby to the chic sophistication of its guest rooms, every corner exudes beauty. With its central location and impeccable amenities, it’s a haven of refined comfort and exquisite style.

Luxury: The Ritz-Carlton, Boston, epitomizes luxury and refinement with its exquisite architecture and opulent interiors. Majestically blending classic elegance with modern sophistication, every detail exudes beauty. From the grand lobby adorned with crystal chandeliers to the plush accommodations offering sweeping city views, it’s a haven of unparalleled splendor and charm.

Chicago vs Boston: Which Is Better?

Overall, while they may be different, Boston and Chicago are both beautiful, brilliant cities. They’ve got fabulous food, super sports teams, and lots of interesting things to do, whether it’s the museums and theaters of Chicago or the historical landmarks and centuries-old buildings of Boston. But which one comes out on top?

Well, as this guide has shown, Chicago just about edges past Boston in a lot of key areas. It’s got the better live entertainment scene, a wider range of attractions, unbeatable nightlife, and the kind of food that keeps you coming back for more. So, if you’re hesitating between these two cities, Chicago is probably the one to see first.

But still try to make time for Boston, if you can. As one of the oldest cities in America, it’s a veritable must-see for history buffs, and there’s something truly special about walking around the country’s first ever public park (Boston Common) or visiting age-old structures that played such big roles in the development of America as we know it today.