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We Chicagoans will brag to anyone who’ll listen about how great our city is (if you’ve ever met one of us, you probably already know this). But go ahead and disregard our 2 a.m. bar ramblings (did we mention we have the best bars in America?), here on paper is the definitive guide to why Chicago is America’s premiere coastal city—yes, Lake Michigan counts as a coast!
Wrigley Field is a better ballpark than Boston’s Fenway

Trover photo by Bill Lang
It’s a fierce rivalry and we’ll give Fenway, which opened in 1912, its status as the oldest MLB stadium as well as its famous Green Monster wall. But ivy-covered Wrigley Field (which opened two years later) handily wins the debate. It all comes down to neighborhood. Wrigleyville, a micro-nabe located within the larger Lakeview, bustles with energy 24/7 including an ebullient bar and restaurant scene, apartment buildings famous for their peek-a-boo views of the baseball diamond and proximity to the Lake. Fenway has some bars and restaurants, but it also has a major freeway roaring just beyond its outfield. Recent renovations have only cemented the Friendly Confines’ ruling status.
DON’T MISS: The new Hotel Zachary, top-notch eateries Mordecai, Big Star and West Town Bakery & Tap, and classic Cubbie bars Sluggers and Murphy’s Bleachers.
The 606 is a better elevated greenway than New York’s Highline Park

Trover photo by throwingsofas
Yes, we have our version of the Highline Park, the much hyped elevated rail line turned public park that runs through Manhattan’s West Side and has caused rents surrounding it to skyrocket. But while theirs is overrun with selfie-wielding tourists, ours is overrun with—gasp!—actual locals. The 606 (aka Bloomingdale Trail), offers 2.7 unobstructed miles (nearly twice the size of the Highline!) of elevated greenway running east-west through three classic Chicago neighborhoods (Logan Square, Humboldt Park and West Town). Unlike the Highline, the 606 isn’t just a beautiful place to idyll, but also as a legit transportation corridor moving locals that much closer to where they need to go. Take that, NYC!
DON’T MISS: Highlights near on/off points including daring desserts at Mindy’s Hot Chocolate, killer burgers at Small Cheval and Donut Delight inside a car wash.
Move over Art Deco Miami, our architecture is way more impressive

View from an architecture tour | Trover photo by Head of the fort!!
A round of applause for the hundreds of buildings dotting flashy South Beach. Largely done in Art Deco, a style popularized during the the ’20s and ’30s and defined by bold geometric and curvilinear forms and, in Miami’s case, pastel colors, they’re a delightful substitute for the city’s sorry skyline. But they don’t hold a candle to Windy City architecture (few cities do). Chicago provides a blueprint for how 20th-century America was constructed, thanks largely to the Chicago School of Architecture and its use of steel frame construction. Because of Louis Sullivan, Burnham & Root, Frank Lloyd Wright, Mies Van der Rohe, Jeanne Gang and others, you can spend hours just staring at the city.
DON’T MISS: The Water Tower, skyscraper forerunners the Chicago Building and the Reliance Building, Wright’s Robie House and Gang’s Aqua Tower plus the city’s famed Architectural Boat Tours.
Our 22 miles of coastline rival LA beaches any day

View from North Ave Beach | Trover photo by Ryan Miller
Sunbathing in Malibu, you might be inclined to think you’ve found paradise on earth; just remember that Malibu is not part of the city of Los Angeles and neither are the beaches in Santa Monica for that matter. In fact, if you consider LA’s actual coastline, the only respectable beaches within city limits are in Venice and Pacific Palisades. While we adore both, they hardly compare to Chicago’s 22 miles of unobstructed coastline boasting the skyline on one side, endless horizon on the other and the energetic Lakefront Path.
DON’T MISS: Skyline views at Oak Street Beach, proximity to nature at 12th Street Beach, the party scene at North Avenue Beach and pooches at Montrose Dog Beach.
We boast more LGBT milestones than San Francisco

Trover photo by Maegen Bohac
The first gay right organization in the U.S. formed in San Francisco, right? Nope, that distinction belongs to the Society for Human Rights which formed in Chicago in 1924. But the anti-sodomy repeal movement began in SF, right? Nope, that happened in Illinois in 1962 (repeal didn’t come to the Golden State until 1976). Isn’t the Castro the first gay neighborhood? Actually, the City of Chicago was the first in the country to formally designate a neighborhood as LGBT. But surely San Francisco boasts the first ever leather bar? Sorry, that distinction belongs to the Gold Coast which opened in Chicago in 1958. SF is a great gay city, but Chicago’s LGBT milestone are downright monumental.
DON’T MISS: Gay nabes Boystown and Andersonville; bars Sidetrack, Progress and the Closet; Hollywood Beach and gay street fair Market Days.
We’ve got a cooler musical heritage than Seattle

Trover photo by Dina Zigaeva
Seattle, we’ll give you Jimi Hendrix. But when it comes to the battle of the bands, it’s a coin toss. Seattle’s got Nirvana, Foo Fighters, Soundgarden, Pearl Jam and Heart while Chicago boasts Wilco, the Smashing Pumpkins, Rise Against, Liz Phair, Ministry and, of course, the band Chicago. So why tip the scale in the Windy City’s favor? Because, duh, blues and jazz are both central to the city’s cultural identity and musical genre house music was invented here. Not to add insult to injury, but Pearl Jam’s Eddie Vedder was born and raised in Chicago (and partially in San Diego) and Foo Fighters’ Dave Grohl discovered punk and attended his first concert while spending the summer in, you guessed it—Chicago.
DON’T MISS: The prestigious Chicago Theatre, rock ‘n’ roll at the Metro, Aragon Ballroom, Schubas and Thalia Hall , jazz at the Green Mill, blues at Buddy Guy’s Legends and annual rock fest Lollapalooza.
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Absolutely… but everybody already knows !
My love for Chicago goes back to my very first visit to the “Windy City”. That was a number of decades ago. It was, to be exact, 1972.
I suppose the 2400 shootings there’s been here this summer alone in this hole of the city is something to brag about too.
It is, Devon. Additionally to what was listed in the article, we also have THE BEST crime!