Finding The Bears:  Guide To The Windy City – Gay Chicago! !

Gay Chicago, Illinois Gay Guide Photo 3

Bundle up boys – it's the our staff here with the scoop on one of the coldest cities in America to have hot man on man sex. Chicago, the Windy City is full of interesting tourist attractions during the day and two sexy gay neighborhoods at night. Located on the shores of Lake Michigan, Chicago is fun for any and all studs, divas, drag queen, twinks, kinks and gay bears who want to visit.

Chicago is the third largest city in America and is considered one of the 10 most influential cities in the world.

Long famous as the headquarters of the most notorious gangsters in the world – including Al Capone and Sam Giancanna, Chicago has recently cleaned up it's act and has become one of the safest and most crime free cities in America.

Don't Freeze Your Balls Off in Gay Chicago!

If you go in the winter, dress as warmly as possible. Temperatures often dip as low as 17 degrees, with the enormous wind chill factor making it feel like you are well into negative numbers. There is also a lot of snow in the winter – which can make getting around difficult if you don't have access to a four-wheel drive vehicle.

Gay Chicago Winter

That said, temperatures can go up into the 80s and 90s in the summer – so Chicago actually offers a wide range of weather for you to enjoy and endure.

Many city residents avoid cars altogether and use the public transportation system known as The Loop to get around. It has a great reputation and can take you almost anywhere you want to go in the Windy City.

Whether you are looking for fabulous shopping, hot nightclubs, or some of the greatest views in the Midwest, you'll want to give Chicago two thumbs up!

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In other words – you'll have a gay old time!

So get ready; don't let the wind mess up your fabulous hair, and boytoy is going to show you the ins and outs of Chi-Town!

The Sears Tower

Perhaps the most famous Chicago landmark, The Sears Tower used to be considered the largest skyscraper in the world. Today it is still the most popular and most visited attraction in Chicago and it continues to dominate the city's skyline.

The Sears Tower is 1,353 feet tall and features an extensive museum documenting the history of The Windy City and Chicago's vision of itself for the future.

Gay Chicago Sears Tower 1

Yet, most people visit the tower in order to get up to the top floor Skydeck. Entering on Jackson Street allows you to ascend to the summit of the Sears Tower where, on a clear day you can see as far as 50 miles in any given direction.

That means you can see five states while standing in one place!

How delicious is that?

Buckingham Fountain

Modeled after the architecture of Versailles Palace in Paris, Buckingham Fountain is considered the largest outdoor fountain in the world. It's located inside Grant Park and offers a fabulous 20-minute long fully choreographed water display once an hour. With the accompanying light show, it just may be the most fabulously gay attraction in the Windy City!

Gay Chicago's Buckingham Fountain

The showcase of the fountain are the four giant seahorses that represent the four states - Michigan, Indiana, Illinois and Wisconsin – the border Lake Michigan.

Grant Park itself is beautiful and safe and a great place to spend an afternoon watching the boys go by.

The Navy Pier

While, unfortunately, you might not meet a lot of sailor boys, the Navy Pier is the second most popular attraction in Chicago, and a great place to spend an afternoon eating and shopping.

Gay Chicago Navy Pier

It opened in 1995 and since then has become a tourist mecca. The highlight is the 15 story tall McDonald's Ferris Wheel – which is guaranteed to bring out the kid in anyone. If you head over to the South Dock you can take a cruise around Lake Michigan and see a great view of the city from the water.

The Pier covers 50 acres of land and features a ton of great restaurants and the best shopping Chicago has to offer. You might want to avoid the area around the three story Children's Museum, however, because it is packed with loud breeder families and their spawn – but hey, no place is perfect!

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The Hancock Observatory

While not quite as high as the Sears Towner, The Hancock Observatory has something the skyscraper doesn't – an open-air view of the entire city. Because this 1,000 foot tall observatory is located outside instead of inside you'll be able to feel all of the wind of the Windy City in full force while you check out the incredible views the lake and the city itself.

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Located on North Michigan Avenue, many tourists like to bring cameras and camcorders along with them to record the sites and sounds of the city from a bird's eye view.

You can also rent an audio tour which will provide an interesting historical perspective on the city and it's rich history.

Millennium Park

Home of the Crown Fountain, Millennium Park is a 24 acre green space dedicated to the diversity of Chicago and it's visitors.

The Park is considered the cultural center of Chicago and is home to concerts, art exhibits and other progressive artistic events. The Jay Pritzker Pavilion is considered the most state of the art concert venue in the United States.

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Yet, it is the Crown Fountain that keeps people coming back to the park time and time again. Two 50-foot glass block towers sit on either side of the giant reflecting pool. Then, constantly changing images are projected both into the pool and onto the two block towers – each one telling a story about the diversity and acceptance of the people of Chicago. It's a must see tourist attraction!

The Lincoln Park Zoo

You don't have to hit the gay ghettos if you want to check out some cool bears. The Lincoln Park Zoo is one of the only free zoos left in America. Located just outside the city you have the chance to look at lions and tigers and, of course, bears

There are more than 1,000 mammals, reptiles and birds here. The best part is that the entire city skyline overlooks the zoo, so when you check out the cool animals in their natural habitat you have a totally fabulous cityscape as a contrasting background.

The Magnificent Mile

If you want to shop til you drop, The Magnificent Mile is where you want to go in Chicago. Starting on State Street you'll have access to more than 900 stores, shops, boutiques and high-end department stores.


Head to the Armitrage Avenue section of The Magnificent Mile for the largest selection of jewelry stores in the Midwest and then go to the Bucktown section for artsy bohemian shopping.

Stay on State Street if you want to find the best and most fashionable stores on The Magnificent Mile. It's a great place to upgrade your wardrobe or do some holiday shopping for your friends and family.

There is almost always a sale of some type going on in The Magnificent Mile, so bargain hunters will feel just as fabulous as their delicious friends with deep pockets.

Boystown in Gay Chicago

Now that you've seen the sites and been a good boy during the day, it's time to get down and dirty and be a hot stud at night. That's why you need to visit Boystown – the first officially recognized gay village in the United States with tons of hot boytoys walking around!

Gay Chicago Boystown Sexy Guy

Located in theLakeview neighborhood, Boystown is considered one of the largest gay communities in the United States.

It is estimated that more than 300,000 gay, lesbian, bisexual or transgendered people live, work and play in Boystown everyday.

The neighborhood is located between Addison Street in the North and Belmont Avenue on the south and features tons of gay friendly shops, gay bars, cabarets, theaters and smoking hot gay clubs.

Since 1970 Boystown has been the center of the annual Chicago Gay Pride Parade. The 2006 Gay Games were also held in Boystown.

Since 1998 Boystown has been officially recognized by the city with 11 pairs of rainbow colored art deco pylons.

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So, come to Boystown and get ready to get blinded by the gay!


If Boystown is too intense for you – or if you've already hit all the gay bars and banged the hot boys you want in Boystown, you might want to head out to the newest gay mecca in Chicago – Andersonville.

Located between Winnemac Street on the south and Peterson Avenue on the north, Andersonville used to be the Swedish Ghetto, but has become a gayborhood over the past 10 years.

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The center of gay life in Andersonville is Clark Street, where you'll find tons of gay friendly shops and restaurants during the day and hot gay bars and nightclubs at night.

It's where the boys are!

Come Out And Cum In The Windy City!

Why not plan a visit to the Windy City?

You'll have plenty of tourist things to tell your straight friends and fag hags about – while you cruise Boystown and get your grove on.

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