Chicago vs Boston: picking the perfect city for your fall break


The prize of the Midwest, or the jewel of New England?

We don’t envy anyone who can only visit one of two of the most dynamic cities in the US: Chicago and Boston. Nonetheless, we’re here to help, turning to a pair of local correspondents to explain why you should never consider visiting anywhere other than their hometown.

A boat on the Chicago River, dyed green for St Patrick’s Day, Chicago, Illinois, USA
Chicago loves a party so much that city authorities dye its river green each St Patrick’s Day © TZIDO SUN / Shutterstock

Chicago: one toddlin’ town

Karla Zimmerman lives in Chicago, where she has been testing bar stools and yelling at the Cubs for the last three decades.

You’re looking for a city, right? A big, teeming, tall-skyscraper buzz of energy? That’s Chicago – no contest. It’s five times the size of Boston with four times the population. Which means that much more awesomeness to soak up. 

Think about it: when Hollywood needs an authentic, moody metropolis to set the scene for, say, The Batman or The Bear, does it go to Boston? Nope. It spotlights Chicago, where the hulking skyline juts into the clouds, the L train rumbles by and 2.7 million people work, play and eat great food.

Chicago is a star.

And that’s no surprise. Consider the architecture. Chicago invented the skyscraper – and then went right on pushing the boundaries of modern design. You’ll have a neck-ache from looking up at all the beaux-arts beauties, art deco landmarks and International Style edifices: a Chicago Architecture Center boat tour tells their stories as you glide by. Head (way) up to check out the stomach-lurching views atop the Willis Tower, one of the world’s tallest buildings. Can you get this high in Boston? Not even close.

Tourists visit Cloud Gate (“The Bean”) in Millennium Park in the evening, Chicago, Illinois, USA
The architecture of Chicago never disappoints © Sean Pavone / Shutterstock

Chicago’s museums also rock. The most Impressionist paintings outside of France hang at the Art Institute. The western hemisphere’s biggest science trove fills the Museum of Science & Industry. And the planet’s largest dinosaurs menace the Field Museum.

The brewery capital of US

OK, we now concede a point to Boston for its history sites. But Chicago has beer – as in more breweries than anywhere else in the country. (We have our priorities straight.) Revolution Brewing and Lagunitas Brewing Co host good-time taprooms, while Malt Row unfurls a walkable corridor of old factories-turned-breweries to stroll between pilsners, lambics and chocolate stouts.

Stellar beer calls for stellar food, and Chicago chefs have earned a heap of Michelin stars and James Beard Awards to prove they out-cook Boston. Despite the accolades, diners find an affordable, come-as-you-are scene with a neighborhood bent. Areas like Pilsen, Logan Square and Wicker Park show how it’s done, where inventive storefront restaurants are backed by magic-making in the kitchen.

Detail of caviar at Michelin-starrred Kasama, Chicago, Illinois, USA
At Michelin-starred restaurants like Kasama and neighborhood joints alike, it’s hard to have a bad meal in Chicago © Chris Sweda / Chicago Tribune / Tribune News Service via Getty Images

Let’s get down to the nitty-gritty: sports. Boston and Chicago are both top-notch sports towns, probably America’s best. Each city has pro football, basketball, baseball, soccer and hockey teams, along with plenty of hard-core fans. We won’t wade into the Wrigley Field versus Fenway Park debate, because they’re both phenomenal. But we will give the edge to Chicago when it comes to wandering into a corner tavern, ordering a beer and watching a game. No doubt your barstool neighbor will start filling you in – who’s a hero, who should be traded, some random gripes about the mayor – and you’ll be high-fiving pals by night’s end. Such is the Chicago way.

There’s so much more to get to: Chicago’s unbeatable theater scene, led by dramatics at Steppenwolf and goofy improv at Second City; 20-plus beaches for wave splashing and sandcastle building along sea-sized Lake Michigan; and a public transport system that runs 24/7, unlike Boston’s.

But maybe it really comes down to this when making the case for one city over the other: which place celebrates big enough to dye its river green each year on St Patrick’s Day? You know the answer.

Chicago is the town that won’t let you down.

The Institute of Contemporary Art at dusk, Seaport District, Boston, Massachusetts, USA
Discover exciting new neighborhoods along Boston’s revamped waterfront © Wangkun Jia / Shutterstock

Boston: head to the Hub

Bostonian Mara Vorhees has been writing about her hometown (and the rest of New England) for more than two decades. Her favorite way to spend a morning is riding her bike along the Charles River. 

I am a Midwesterner by birth and a New Englander by choice, so I feel well qualified to weigh in here. And considering that I have lived in Boston for the past 25 years, you can guess which side of the debate I’m going to take. For its long and influential history, for its lively contemporary culture and college-town atmosphere, and – oh yes – for its incomparable regional cuisine, Boston is the hands-down winner in this contest.

For starters, consider the nearly 200-year age difference between the two cities. Founded in 1630, Boston claims a long, proud and world-changing history. This is where the Puritans established their City on a Hill and where the American Revolution began: vestiges of this storied past are all around town. You can reenact the Boston Tea Party, or follow the route of Paul Revere’s ride out to Lexington and Concord, or visit the site of the turning-point Battle of Bunker Hill, or pay respects at the gravesites of the patriots who made it happen. You can even get a beer at the Warren Tavern, a Charlestown bar where George Washington was known to drink.

Re-enactors dressed as Redcoat soldiers by The Old State House, Boston, Massachusetts, USA
Visitors find it hard to escape Boston’s peerless contributions to American history © Sergi Reboredo / VW Pics / Universal Images Group via Getty Images

With all its rich history, you might think that Boston is a city that’s living in the past – but you’d be wrong. Athens of America no more, Boston is at the forefront of contemporary culture. This is in part due to the dozens of institutions of higher education, which are an ever-renewable source of creative energy. Boston’s schools train their students to break down established boundaries: in arts and culture, in science and technology, and at the intersection of all of the above. 

What does this mean for you? It means exploring new eye-catching and eco-friendly buildings at Boston University and Massachusetts Institute for Technology (MIT). It means catching a groundbreaking performance at the American Repertory Theater. It means hearing mind-bending music at local clubs and seeing perplexing art installations at local museums.

The truth is that Boston is a small city. It’s less than half the size of Chicago in terms of land area, and has a mere quarter of its population. Yet it churns out art and innovation to rival any of the USA’s cultural capitals.

Don’t get me wrong: there’s plenty to love about the City by the Lake. But when it comes to a waterfront setting, the only thing better than a Great Lake is…an ocean! Boston’s revamped waterfront offers whale-watching tours, harbor islands to explore and swimming that’s every bit as cold as Lake Michigan. Best of all, the North Atlantic keeps Bostonians well fed.

Two seagulls soar above Spectacle Island, with the cityscape in the distance, Boston, Massachusetts, USA
Fun by the water awaits on the islands of Boston Harbor © Getty Images / iStockphoto

Lobster pizza or lobster roll

There is no Midwestern match for the fresh, succulent seafood that will tantalize your taste buds in Boston. All the walleye in Lake Michigan cannot compete with the simple perfection of a lobster roll. The seafood options are many, ranging from classic clam chowder to internationally inspired innovations. And it turns out that lobster is a delicious addition to almost anything. Lobster pizza? Lobster ravioli? Lobster Benedict? Yes, please.

One last point, as it’s impossible to write about Boston and Chicago without mentioning the weather (highly variable, in both cases). Yet surprisingly, the Windy City comes in behind Boston for average annual wind speeds.

So hold on to your hat – and start planning your trip to the Hub of the Universe.



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