Despite the endless offerings of big city sophistication, for the token GLBT 10% of 29 million annual visitors, Chicago has only three main avenues: Belmont, Waveland, and Michigan. Loud and proud, twenty two rainbow ringed pylons tower over Halstead Street between Belmont and Waveland, defining the pulsating heart of Chicago’s official LGBT neighborhood, Lakeview, affectionately and appropriately known as Boystown. This is one neighborhood where gay boys rule the streets; they make the rules, break the rules, and live unaffected by outside prejudice. It’s an entire enclave dedicated to embracing the church’s Seven Deadly Sins through excessive alcoholic intake at America’s “best gay bar” (Sidetracks), casual sex at the nation’s most visited sauna (Steamworks) or devouring the eye candy at the local Caribou Coffee (known as Cruise-i-bou).  

Three miles north, the former sleepy Swedish village known as Andersonville houses a new, second gayborhood, predominantly attracting Chi-town’s lesbians. The neighborhood combines the likes of lipsticks, Home Depot homebodies, and cropped hair militants that insist on spelling women with a  “y,” shining as a rare region where gay womyn are spoiled for choice. The queens priced out of Boystown, the IML couples that reached the 5 year milestone, and those who abused their Steamworks annual membership have also begun the pilgrimage north, raising neighborhood property values. For some, Andersonville’s growing hardcore leather scene and clubs like Touche, Crew, and Jackhammer are a welcomed reprieve to Boystown’s pretty boy palladiums like Circuit Nightclub 2.0, Charlie’s, Hydrate, Roscoe’s and Sidetrack.

Venturing towards downtown, the world famous Michigan Avenue remains the Midwest’s most popular tourist attraction, namely along the Magnificent Mile.  This short stretch showcases Chicago’s archetypal architecture and landmarks, some of the tallest buildings in the world, several of the city’s most revered hotels, flagship department stores and corporate favorites, and hundreds of luxury boutiques for designer label whores. At the southern end of the magnificence lies the awesome Millennium Park, the urban park cum postmodern architecture opus, which cost the city and donors nearly a half a billion dollars. The contemporary prowess is most visible at the colossal stainless steel Jay Pritzker Pavilion (designed by Frank Gehry), the interactive glass bricks of the Crown Fountain, and the city’s ultimate Facebook photo opp – a snapshot of your reflection underneath the 110-ton steel Cloud Gate locally known as “The Bean.”

As summer approaches, Chicago residents spend less time gorging on the buttery crust of deep-dish pizza at Gino’s East and Lou Malnati’s and more time doing the Cell Block Tango at the Bally’s in Lakeview to show off at the local Hollywood “gay” beach. With impending kinky shenanigans at International Mr. Leather in May, Gay Pride in June and the almighty Halsted Street Market Days in August, summer judgment days mean getting in top form by the end of April. Daily jogs along vibrant Lake Michigan are the perfect physical remedy and mental therapy for looking fit during the summer’s many sidewalk sales.

Without a doubt, Chicago leaves a lasting impression as a city imbued with American ideals, harmonized diversity, and a strong sense of pride. It’s one of the world’s great cities, easily accessed from anywhere and everywhere in the United States, a shining star on the gay global map! 

The Windy City’s Best Crash Pads

The Park Hyatt Chicago asserts its dominance in Chicago’s world of 5 stars, through its modern elegance and stellar service. Occupying fifteen floors of the narrow Park Tower skyscraper, the Park Hyatt Chicago boasts 202 sleek, straight-edged contemporary sanctuaries. The unobstructed views from higher floors layer the visually arousing tumult of big city architecture over the placidity of Lake Michigan. Slender day beds nestle the near floor to ceiling windows, ideal for inspirational reads, thoughts, and glasses of Chardonnay. The garden at NoMI, the hotel’s prized restaurant, is a summer hotspot for high-end LGBT locals. The 7^th floor outdoor urban escape is the city’s sexiest cocktail hideaway, with sweeping panoramas of Chicago and divine interventions of mixology.

Those on a budget and less concerned with bragging rights should consider the Best Western Hawthorne Terrace. Located in the heart of Boystown, the adorable Hawthorne Terrace is an outstanding exception to the commonplace no-frills, no thrills feel of Best Western properties. The beautiful and welcoming redbrick, colonial exterior is complemented by the functional 3 star interiors. The hotel’s location makes it an ideal choice for a weekend of partying in Boystown or immersing yourself in the city’s fabulous gay ghetto.

Getting High

The Sears Tower, now called the (Whatchu Talkin’ ‘Bout) Willis Tower, reigned as the tallest building in the world from the 70s to the 90s until Miss Malaysia unveiled the PETRONAS Twin Towers in Kuala Lumpur. Nevertheless, the 108-story, 1451 foot skyscraper is still the tallest building in the United States and one of the highest occupied spaces in the world. Amazing views of the city and even neighboring states beckon on a clear day from the 103rd floor Skydeck. Those easily subject to vertigo might want to give this one a pass, especially since the building sways on windy days. Additionally, those who reserve their budget principally for alcoholic consumption and savvy bargain hunters may want to bypass the Sears Tower $16 entrance fee and have a $12 martini at The Signature Room on the 95th floor of the John Hancock Building. The food isn’t particularly great, but the drinks are decent, entrance is free, and the views are almost as spectacular as the Skydeck. (www.the-skydeck.com; www.signatureroom.com). 

Chicago Eating, Snacking, and Knoshing (by local residents and power couple, gay cousin Bernard & Danny)

Ping Pong (Boystown) This is a fun place that boasts inexpensive “chopstick cuisine” and minimalist décor. Tip: Remember to Bring-Your-Own-Bottle of wine, with no corkage fee!

Chicago Diner (Boystown) A grungy vegetarian and vegan restaurant, with great dairy-free desserts.

Kit Kat Lounge (North Boystown) An enormous Martini list and a reasonably priced European menu. Tip: Bring dollar bills and your camera for the fabulous surprise entertainment!

Windy City Sweets (Boystown) Delicious Kosher ice cream, homemade fudge, incredible chocolates, and a Jelly Bean buffet!

Green Zebra (North of the city center) An almost completely vegetarian taster-style menu, with fantastic décor and service. It’s not cheap, but it’s well worth it. Book well in advance.

TRU (The Magnificent Mile) For one of the most incredible dining experiences of your life! Book well in advance. Dress code applies. Tip: Order the “TRU collection.” Also, you can book for dessert only.

Vosges Haut-Chocolat (The Magnificent Mile) Pure decadence. Enjoy a truffle, a slice of toffee, and a cappuccino at the bar. Bernard’s tip: There are always free samples to try.