Gay Chicago

Chicago may not be top of your list of must see places in the US for the LGBT traveller but it should certainly be up there in your top five. The city is home to over 400 000 corn fed mid west boys who live in a city that positively embraces all things alternative and even has the first officially recognised US gay village as well as legally recognised gay marriage within state boundaries.  

Having made several visits to many of the US’s main gay destinations I found Chicago to be the most refreshing. It’s not as pretentious as LA, not as body conscious as Miami, not as abrupt as New York and not quite as old as San Francisco, Fort Lauderdale or Key West. I found Chicagoans to be welcoming, broad minded and comfortable with themselves going out of their way to talk to visitors.

This is also the city that hosts the infamous International Mr Leather contest (IML) which at the time of writing had just celebrated its 33rd year. This four day event that falls over the Memorial Day weekend (end of May) attracts leather lovers and fetish freaks from all corners of the globe that come to Chicago to shop, party and socialise taking over all 2000 rooms of the Hyatt Regency Chicago hotel proving that this city is broad minded in the very widest way.

Although known as the ‘Windy City’ Chicago is actually no more windy than any other American city. Some say the title came from Chicagoans being made out to be terrible show off’s by its arch rival and neighbour Cincinnati.  Others say it could have something to do with the cooling lake breeze that stops the city being unbearably hot during summer while another theory is the wind can sometimes be felt whistling through the tall sky scrapers. Windy or not the best time to visit would generally be between May and October when the weather is mild to warm. That said the city can often experience four seasons in a week as I discovered on my week there at the end of May.  I arrived to cold winds, rain, fog and temperatures around 12 degrees and found myself rushing out to buy a hat and sweater. By the end of the week I was walking around in shorts and t-shirt in clear blue skies, hot sunshine and 30 degrees. So be prepared.

Where to Stay

I stayed at the Hyatt Regency Chicago (151 East Whacker Drive) over the International Mr Leather weekend and cannot recommend it enough. Any hotel that manages to play host to several thousand gay men in various forms of fetish gear for four days and nights and make them all feel welcome without battering an eyelid gets my praise. Even I, as a fairly broadminded gay man who’s well versed in the ways of the fetish scene found myself ever so slightly shocked at the sights I saw and was incredibly impressed with the friendliness and professionalism of the hotel’s staff. 

The Hyatt has also just completed a $90 million refurbishment and offers luxurious accommodations, a fully equipped fitness centre, several eating and dining options and an enviable location on the banks of the Chicago River just minutes from the Magnificent Mile.  

I’ve complied my personal ‘Top Ten Tips’ of things you should do while in the city all of which I did apart from one. There are of course hundreds of things to see and do and I recommend the following research resources:

Explore Chicago is the city’s official tourism site.

Best Gay Chicago guide is regularly updated with Gay and Gay-Friendly, GLBT and LGBT News, Entertainment and Events.

Gay Cities is the online guide for all things gay in many of the world’s major cities.  

Not gay but with gay listings be sure to check out the weekly online edition of the Chicago Time Out guide.

City Bus Tour

There is no better way of familiarising yourself with a city than from the top deck of a bus. Better still if it’s an open top one. The Chicago Trolley & Double Decker Co operate trolley buses as well as double deckers that do a fourteen stop, hop on – hop off route stopping at all the major tourist attractions. Tickets can be bought on board, are valid all day and all buses are fully narrated.

Chicago Architecture Boat Cruise

To fully appreciate Chicago’s architecture hop on board a boat. Shoreline Sightseeing operate several tours each day including Architecture River Cruises, City by Night and a Lake Fireworks Cruise.  I took a one hour Architecture Cruise that was incredibly relaxing and informative. Viewing the city’s famous buildings from the water gives you a totally different perspective than from the bus and the information given is so informative you really come away having learnt something of the history of the city. Make sure you cover yourself in sunscreen and wear a hat if it’s a hot day. I did my tour when the temperature was 32 degrees and nearly fried! Thankfully cold drinks can be bought on board. Highly recommended.

City Segway Tours

You might have seen a Segway at some airport somewhere in the world. They’re those funny two wheel things that are often used by police officers to whiz around the terminal and look a bit like they’re from some sci-fi movie and I bet you always thought you’d love to have a go. Well now you can. City Segway Tours operate escorted tours throughout the city passing well known landmarks and along the lake front. There’s a full commentary given by the guide and safety helmets are provided. Unfortunately I didn’t get to give it a go but passed several groups that looked like they were having a blast and definitely want try it next time.

Shop The Magnificent Mile

Michigan Avenue more widely known as The Magnificent Mile is to Chicago what Oxford Street is to London or Fifth Ave is to New York. This attractive tree lined boulevard is home to every well known brand. There are always discounts and promotions especially at the malls where it’s worth calling at the visitors desk before shopping for books of coupons and discounts especially for visitors from out of town. When I was in the city last weekend of May almost every store I visited had a Memorial Day sale on with huge discounts.   

Northalsted (Boystown)

Officially the first recognised ‘gay village’ in the US, Northalsted (more commonly known as Boystown) is the heart of all things gay in the city and is an eclectic mix of bars, restaurants, coffee houses, places to shop and night clubs. It runs several blocks along Halsted Street starting at Belmont Avenue in the South to Irving Park in the North. It’s easily reached by the CTA train system. I suggest taking the train to Belmont Station on the Red Line and heading north up Halsted from there.

Side Track Bar

Be sure to head to Side Track (3349 North Halstead at the heart of Boystown) which has been voted the US’s best gay bar. This modern industrial feel space is all glass and chrome on several floors with an expansive open air deck space and attracts a mixed crowd of sexy muscle boys and hairy daddies. The Sunday afternoon show tunes sessions that segway nicely into sounds of the 60’s and 70’s complete with video screens are not to be missed.

Great fun, great boys and a great atmosphere! 

Skydeck Chicago at the Willis Tower

Formally the Sears Tower which was at the time of its completion in 1973 was the tallest building in the world, the Willis Tower is a 108 story skyscraper that houses The Skydeck experience, Chicago’s most popular tourist attraction. Elevators take visitors to the 103rd floor in sixty seconds from where they can experience incredible views of the city as well as the plains of Illinois and across Lake Michigan. Not to be missed are the recently opened glass balconies that extend four feet out over Whacker Drive allowing visitors to look down to look through the floor to the street 1,353 feet (412 m) below. Not for the faint hearted!!

Alcalas Jeans

If it’s a new pair of jeans you’re looking for then head to this gold mine of a find. Located in West Town (1733 W Chicago Ave) Alcalas Jeans looks like the sort of place you’d expect to find cowboys kitting themselves out at before saddling up down at the ranch. Row after row of all the well known American brands such as Levi’s, Lee Cooper and Wrangler are available in every style, size and colour. Other items on sale include hundreds of styles of cowboy boots, western shirts and hats. The prices are way lower than the department stores and a trip to the store is a shopping experience in its own right!  

Lunch at Barney’s

Ok so this isn’t New York but that doesn’t mean you still can’t have a Sex and the City moment in the Windy City. I’ve always been a fan of the upscale New York store Barney’s and was thrilled to find a branch of the Madison Avenue store in Chicago (15 East Oak Street). Barney’s is well known for attracting ‘ladies that lunch’ to its top floor restaurants called Fred’s (Barney… Fred…  get the connection yet? Yabba dabba doo!!)

Fred’s is known for serving the most wonderful food that’s perfect for lunch. Think lobster bisque, robiola with truffle oil pizza, fresh pastas, baltimore crab cakes or its famous Mark's Madison salad.  Add to that a crowd that looks like Carrie, Samantha, Miranda and Charlotte and you get the picture. Great food and fabulous people watching darling!!

Water Tower Place

If you love an American Mall then Water Tower Place is not to be missed. Located at the top end of The Magnificent Mile its home to over 100 stores many exclusive to Chicago. Shopping is laid out around a stunning eight level atrium and there’s a great food court.

Top Tip… American gay boys have long since fallen out of love with Abercrombie & Fitch and have turned to rival American Eagle for their fix of muscle T’s, shorts, vests and cargo pants. Prices are far lower than A&F and most look almost identical. The promotions are too good to miss and at my time of visiting were along the lines of ‘take an extra 30 percent off the already reduced sale price’! Rivalry between the two brands is now so fierce that you’ll often find them located on the same street. At Water Tower Place they’re located next door to each other!

I travelled to Chicago on Memorial Day weekend which falls over the last weekend of May which is when the Mr International Leather (IML) contest is held. Other times worth visiting the city are for Chicago Pride Fest in June and the Northalstead Market Days in August which is the largest two day street fair in the Midwest.