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Chicago's Miracle Miles

Chicago's Miracle Miles

Shopping, beaches, culture and cute boys: What more can a visitor to the Windy City need?


Stretched along 19 miles of coastline along Lake Michigan, Chicago continues to surprise locals and visitors alike with a metropolitan smorgasbord of eye-popping architecture, internationally renowned museums, and a jumbled mix of ethnic neighborhoods begging to be explored.

The city that birthed the skyscraper is sometimes referred to as a "living museum." It boasts a collection of famous buildings by legendary architects.

The city's cultural life is rich and diverse. You?ll find some of the finest museums in the country like the Art Institute of Chicago. Jazz and blues have deep and lasting roots in Chicago and many live music venues have been around for decades. The Chicago Symphony Orchestra is nationally renowned, while house music, which originated here, is an integral part of the club landscape.

Chicago's gay and lesbian population is large and highly visible. Lakeview, a.k.a. Boystown, one of two thriving gay neighborhoods in the city of Chicago, is located several miles north of the ?Loop,? the city?s downtown area. It?s on Halsted Street that you'll find the highest concentration of gay activity.

Lesbians began settling in the Swedish immigrant neighborhood of Andersonville in the late '80s, and the last decade has seen a dramatic renovation of the entire area, which is now Chicago's second gay neighborhood. Restaurants, hip boutiques, and bars abound.


Chicago's lodging options can accommodate any traveler, and even those on a modest budget can stay in the heart of the action. Most of the gay hotels are located close to the Boystown bar scene in Lakeview. Travelers seeking more luxurious options will find that the city's finest hotels are in the "The Loop," and scattered along Michigan Avenue.

In Boystown, the Hawthorne Terrace Best Western is a great choice, located just blocks from shopping, dining and nightlife. It?s much more stylish than the typical Best Western, showing the company knows who its customers are.
Another good choice for gay travelers is the collection of three boutique hotel properties known as the Neighborhood Inns of Chicago. The crown jewel of the three is The Majestic, located on a shady residential street a few minutes north of the heart of Boystown. City Suites Hotel is steps away from the Boystown strip on busy Belmont Avenue. Willows Hotel is the most European-style hotel in this group -- only a few minutes south of the heart of Boystown.

One of our favorite mainstream hotels is the famous Peninsula Chicago located along Michigan Avenue?s beautiful Magnificent Mile. It?s frequently rated as the top luxury property in the world.

The W Chicago City Center is another decadent destination. Located in the middle of the Loop, the W Chicago City Center is steps away from Sears Tower, Millennium and Grant Park, and the downtown theater district.

The San Francisco-based Kimpton Hotel group offers visitors three very stylish options downtown, including the Hotel Allegro, one of downtown's hippest addresses.

Also in the Kimpton lineup, is Hotel Monaco, where unexpected amenities include "tall" rooms for, well, tall guests, accommodations for your accompanying pet, and even a goldfish companion for lonely travelers.

The most dramatic Kimpton property is the Hotel Burnham in a spectacularly renovated and historically important building, which was the direct predecessor of the modern skyscraper.



Brunch is a time-honored gay institution. Have yours at Orange (Lakeview: 3231 N. Clark St; 773-549-4400) which offers Chicago?s most inspired and unusual brunch menu. If you want to hit dinner then the bars, fly into, FireFly -- a hot romantic spot with great martinis, perfect filets, and legendary desserts.

Make sure to leave plenty of room for the thrilling fixed-price menus at the city?s hottest seafood dining destination, L20. You wouldn?t want to miss out on lobster with Tahitian vanilla or any of the other sumptuous Japanese, Spanish, and New American fusion fare.

If you?ve a late dinner reservation, pop into Eno Wine Room and check out the cheeseboards and wine flights at this chic chocolate, cheese, and wine bar.


Spend the morning exploring Millennium Park, home to many attractions, including the Crown Fountain, two 50-foot glass block towers that project video images of the faces of more than 1,000 Chicagoans, and the magnificent "Cloud Gate" (often referred to as "The Bean" sculpture by locals). Millennium Park garners raves from visitors and civic leaders all over the world.

Next, walk the short distance to the majestic Art Institute of Chicago, a world-class institution featuring lots of those paintings you studied in art history class.

Nearby you?ll find three enticing science museums, all walking distance from each other just south of the Loop: The Field Museum of Natural History features "Sue," the most complete T. rex skeleton ever reassembled; The Shedd Aquarium, the world's largest indoor aquarium, is home to some 8,000 aquatic animals; and the Adler Planetarium.

Downtown Chicago is an architectural feast. The earliest skyscrapers vie for space next to the Wills Tower (formerly known as the Sears Tower) and the John Hancock Building. The best way to learn about the city's architectural history is by taking the Architecture River Cruise given by the Chicago Architecture Foundation.

If you?re staying closer to Boystown, rent bikes from gay-owned Out Spoke'n (1113 W. Belmont Ave; 773-404-2919) and bike the path along Lake Michigan, which runs about 6 miles from the Loop to the Northside past the Lincoln Park Zoo and a few nice public beaches.



Two of the most popular bars in town are Sidetrack
and Roscoe's, located across the street from each other and acting together as the main anchors of the scene. Sidetrack is a video bar specializing in theme nights, and is busy most every night of the week. It's by far the most popular gay bar in Chicago. The roof deck is jammed in the summer months. Roscoe?s is more popular with the early-20 set and has a high energy dance floor. Minibar and Winebar, right next to Sidetrack are also really hot.

Make Circuit, Boystown's largest dance space, your next stop. It offers 3D glitter-effect flooring and a huge dance space.


Attention shoppers: Chicago is mecca for some serious retail therapy. Michigan Avenue between the Chicago River and Oak Street is known as the Magnificent Mile, home to top department stores. Nordstom Michigan Avenue offers hundreds of thousands of square feet of clothes, shoes, and accessories. Water Tower Place (845 N. Michigan Ave.) is the country's first vertical shopping mall, all glass and chrome, with the toniest stores in town.

Over in gay-popular Boystown, spend the afternoon shopping at anynumber of gay-oriented retail options sprinkled along Halsted and Broadway. Bad Boys (3352 N. Halsted St.; 773-549-7701) is Chicago's premier gay outlet for sportswear and clubwear. You?ll also find Gay Mart (3457 N. Halsted St.; 773-929-4272), a knick-knack boutique offering gifts, cards, shirts, and a wild assortment of everything gay.

For gay books: Unabridged Books (3251 N. Broadway St.; 773-883-9119) is the leader. Women and Children First (5233 N. Clark St; 773-769-9299) is an excellent lesbian/feminist bookstore.


Though it?s possibly most fun to visit in the summer when life absolutely explodes along the vast stretches of beaches downtown, Windy City is hot all year, even in the dead of winter. You?ll find energetic nightlife, incredible culture, theater, museums, architecture, great shopping and much more. There?s more than even the most efficient tourist can soak up in one visit. Plan to return again and again. And despite the fact that it?s a huge pulsating city, the locals are authentically nice, thanks to their Midwestern openness.

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