Chicago vs Boston: choosing the ideal city for your autumn getaway

The pride of the Midwest or the gem of New England?

We don't envy anyone faced with the choice between two of the most vibrant cities in the US: Chicago and Boston. Still, we’re here to assist, turning to local insiders to share why you should never think of visiting anywhere but their hometown.

Chicago: a vibrant city full of life

Karla Zimmerman has called Chicago home for three decades, testing bar stools and cheering on the Cubs.

You’re in search of a city, right? A bustling hub with towering skyscrapers and an energetic vibe? That’s Chicago – hands down. It’s five times larger than Boston and boasts four times its population, offering even more excitement to explore.

Consider this: when Hollywood seeks a gritty, atmospheric city for films like The Batman or The Bear, does it choose Boston? No way. It showcases Chicago, where the impressive skyline rises to meet the sky, the L train thunders along, and 2.7 million people engage in work, play, and savor delicious food.

Chicago truly shines.

And it’s easy to see why. Just think about the architecture. Chicago was the birthplace of the skyscraper and has continually redefined modern design. Prepare for a sore neck from gazing up at the stunning beaux-arts masterpieces, art deco icons, and International Style buildings. A boat tour from the Chicago Architecture Center shares their fascinating stories as you float past. For breathtaking views, ascend to the dizzying heights of the Willis Tower, one of the tallest structures in the world. Can Boston compete with that? Not a chance.

Chicago’s museums are exceptional, too. The Art Institute boasts the largest collection of Impressionist works outside of France. The Museum of Science & Industry houses the biggest science exhibits in the western hemisphere, while the Field Museum showcases the world’s largest dinosaur fossils.

The brewery capital of the United States

Alright, we’ll give Boston its due for historical sites. But when it comes to beer, Chicago reigns supreme with more breweries than anywhere else in the nation. (We know our priorities.) Revolution Brewing and Lagunitas Brewing Co offer lively taprooms, while Malt Row features a strollable stretch of converted factories-turned-breweries where you can sample pilsners, lambics, and chocolate stouts.

Exceptional beer deserves exceptional food, and Chicago chefs have racked up numerous Michelin stars and James Beard Awards, proving they outshine Boston in the kitchen. Despite their accolades, diners can still enjoy a laid-back, affordable atmosphere in neighborhoods like Pilsen, Logan Square, and Wicker Park, where creative eateries serve up culinary magic.

Let’s talk sports. Both Boston and Chicago are elite sports cities, arguably the best in America. Each has professional teams in football, basketball, baseball, soccer, and hockey, alongside passionate fans. We won’t enter the debate of Wrigley Field versus Fenway Park because both are incredible. However, we do think Chicago has the edge when it comes to dropping by a local tavern, ordering a beer, and catching a game. Your barstool neighbor will likely fill you in on the latest heroes, trade rumors, and some good-natured gripes about the mayor, with high-fives all around by the end of the night. That’s just the Chicago way.

There’s an abundance to explore: Chicago boasts an exceptional theater scene, highlighted by powerful performances at Steppenwolf and whimsical improv at Second City; more than 20 beaches for splashing in waves and building sandcastles along the expansive Lake Michigan; and a public transportation system that operates around the clock, unlike Boston’s.

Ultimately, it might boil down to this when deciding between the two cities: which one celebrates large enough to turn its river green every St. Patrick’s Day? The answer is clear.

Chicago is the city that consistently impresses.

Boston: Journey to the Hub

Mara Vorhees, a Bostonian, has been chronicling her hometown and the wider New England region for over twenty years. She enjoys starting her mornings by biking along the Charles River.

Being a Midwesterner by birth and a New Englander by choice, I feel well-positioned to weigh in. Having lived in Boston for 25 years, it’s clear which side of this debate I support. With its rich and impactful history, vibrant contemporary culture, and distinct college-town vibe—plus its unmatched regional cuisine—Boston is the undeniable champion here.

To start, consider the nearly 200-year age gap between the two cities. Founded in 1630, Boston boasts a lengthy and influential history that has changed the world. This is where the Puritans established their City on a Hill and where the American Revolution began; traces of this remarkable past can be found throughout the city. You can reenact the Boston Tea Party, trace Paul Revere’s ride to Lexington and Concord, visit the historic site of the Battle of Bunker Hill, or pay tribute at the graves of the patriots who made it all happen. You can even grab a beer at Warren Tavern, a Charlestown pub known to have been visited by George Washington.

With its deep historical roots, one might assume Boston is stuck in the past – but that’s far from the truth. No longer just the Athens of America, Boston is a leader in contemporary culture. This is largely thanks to its numerous educational institutions, which serve as a continuous source of creative energy. These schools encourage students to challenge traditional boundaries in arts, science, technology, and the intersection of these fields.

What does this mean for you? It means discovering striking and eco-friendly architecture at Boston University and Massachusetts Institute of Technology (MIT). It means experiencing innovative performances at the American Repertory Theater. It means enjoying mind-bending music at local venues and exploring thought-provoking art installations in museums.

The reality is that Boston is a compact city. It covers less than half the land area of Chicago and has only a quarter of its population. Yet, it produces art and innovation that can rival any of the cultural capitals in the USA.

Don’t get me wrong: there’s much to appreciate about the City by the Lake. However, when it comes to waterfront beauty, nothing beats an ocean compared to a Great Lake! Boston’s revamped waterfront offers whale-watching excursions, harbor islands to explore, and swimming that’s just as chilly as Lake Michigan. Best of all, the North Atlantic keeps Bostonians well nourished.

Lobster pizza or lobster roll?

There’s no counterpart in the Midwest for the fresh, mouthwatering seafood that awaits you in Boston. All the walleye in Lake Michigan can’t compare to the sheer delight of a lobster roll. The seafood selection is extensive, from traditional clam chowder to globally inspired creations. And it seems lobster is a tasty addition to nearly everything—lobster pizza, lobster ravioli, lobster Benedict? Yes, please!

Lastly, it’s essential to discuss the weather, as comparing Boston and Chicago wouldn’t be complete without it (both are quite variable). Interestingly, however, Boston averages higher annual wind speeds than the Windy City.

So buckle up and begin your adventure to the Hub of the Universe.