I first discovered the glory that is the city of Chicago, Illinois, almost two decades ago. I worked for a finance company in Naperville, about 34 miles outside Chicago, and, being no fool, never did business without adding on a couple of nights in Chicago for pleasure, before returning home, to Toronto.
Chicago, in fact, reminded me of home, and, having visited again this spring, still does. Like The Six, Chicago is a city on a lake; certain times and places alongside it you’d think you were in Toronto; like two pretty sisters who are hard to tell apart – fitting, given the two are actually sister cities.
Located in the mid-West, Chicago’s citizenry are more often than not, noticeably friendly. Almost – but not quite – Canadian nice. And while it’s officially part of America’s Bible Belt, I’ve never once, in all my visits there, felt undue or unwanted evangelicalism (I had to go to Naperville for that.)
Chicago and Toronto often experience the same weather conditions, too, just a day or two apart, typically. Like Toronto, Chicago (unlike many other US hubs) has an actual LGBTQ+ village with a concentrated queer community; Belmont and Halstead are to Chicago what Church and Wellesley are to Toronto, Rue Ste Catherine and St. Hubert are to Montreal, and so on.
And while there’s no place like home, upon closer inspection Toronto might be the “brainy” sister; despite our pretty, Chicago is supermodel gorgeous. Home to some of the most heart-quickening, stunning architecture in the world, the examples that makeup along what is known as the Magnificent Mile (think: Bloor Street) is particularly astonishing. From Art-Deco to Neo-Classical to Gothic towers and modern skyscrapers and bridges, Chicago architecture (the Wrigley building alone!) makes me swoon, every time.
But because incredible architecture abounds, the best way to take it all in and from a truly unique point of view is on a boat tour, and the gold standard is Chicago’s First Lady Cruises. This is the first visit to Chicago where I didn’t actually take the boat tour – but if it’s your first time you must.
This trip I treated myself to an architectural wonder just outside the city that, for all my visits, I had never taken in. (But next time I’m back in Chicago, I’ll take another ride on the First Lady, and make sure it’s one of their Sunday morning yoga cruise.) Taking in the stunning sights while in downward-dog was a new way of seeing the sumptuous surroundings even I’ve never tried.
Back to my side-adventure. A funny thing happened and this video does the explaining.
How I find my way out of my own home some days is beyond me. Onwards… One of the best things about travel: unexpected new friends. It doesn’t happen every time I go away, but when I make a connection, it sticks and I am always delighted at a sudden gift of fate like that.
This trip, I was gifted again. Allen Schwartz is a fabulous Chicago greeter and I could not have been blessed with a more fun, engaging, funny, knowledgeable guide – we’ve stayed in touch since and he owes me lunch. Allen took me to Millennium Park, a $475 million gift to the city by the city that opened in 2004.
The 24.5 acre paradise within the Loop community area is home to a riveting piece of beauty, a bandshell designed by Canada’s own, Frank Gehry, though to call it a “bandshell” doesn’t feel like it does the spectacular creation any justice (see video below) and home to to Cloud Gate the famous “bean” sculpture by Anish Kapoor that draws millions to see it.
Random moment: Back to the lovely denizens of Chicago. While I didn’t make fast friends with this waitress, I almost proposed:
This visit, I found my favourite hotel in Chicago of all the times I’ve stayed here: Steamworks.
Kidding! The Blackstone Hotel is what I call hotel porn. (Not the Tommy Lee / Pamela Anderson rental type of porn, which, actually, I did watch once… in Chicago.) Hotel porn is when design and beauty intersect. When it has its own personality and point of view and is unlike any other “template” design found at many chains. When a hotel lobby (full transparency: I have a hotel lobby fetish) is so aesthetically pleasing and feels so joyful that you’d be happy to sleep right there (never mind with the actual room, whatever it may look like) on the animal print by the reception desk, head resting on a marabou pillow; when the space has an actual point of view, when risk is taken in the decor and humour is given permission to exist and when it (as is the case at The Blackstone Hotel) melds so beautiful with preserved aspects of a former glory, you get hotel porn.
The Blackstone is conveniently located on South Michigan Avenue, and their extraordinarily spacious rooms are chic and understated but luxurious at the same time, with views of Lake Michigan and Grant Park. When I stayed there, the rooms ran approximately $259.00 USD per night.
Notably, the staff err on the side of superbly courteous and authentically engaged. My first name is typically misspelled and my surname often unpronounceable to many, so I appreciated when Eric, who checked me in, took time to check the spelling and ask the pronunciation and proceeded to remember it and say it in greeting me whenever I saw him, which was often during the five days I was there. It’s the little things and I like it when forward-facing professionals are so good at what they do you remember them – and their name – months after.
So taken was I by The Blackstone Hotel, that I spoke with General Manager about its unique history (a dozen US presidents have stayed there,) the time a family returned an item they’d taken when visiting the hotel, and how it got to be so gorgeous, for a recent episode of my SiriusXM chat show after I was back home:
A Few Of My Chicagonian Things
Big And Baby Bites: Chicago has an embarrassment of riches when it comes to dining out, be it casual or a meal to remember. This time, I discovered a couple of fun ways to experience their infamous food scene, and if you’re in Chicago, there’s a rule you must follow at least once each visit.
Revival Food Hall – A collective of all-local restaurants under one roof covering 24,000 square feet, Revival allows you to sample either to-go or to eat-in in a communal setting some of the city’s acclaimed culinary scene. I chose Danke, and sampled the rustic fare found at their full-on restaurant, Table, Donkey and Stick (have you known a … more unique … name for a restaurant? Me neither.) I love this concept and the ability it gives you to try before you invest in a meal out – every city should do this. Or do a few of them!
Latinicity – Sort of like Revival but more focused. World-renowned Chef Richard Sandoval brings together 8 innovative kitchens, a full Mexican restaurant, cafe, bar and lounge, all under one roof to give you his tasty interpretation of Latin street food. It’s located in Block 37, a development located in the Loop community area of downtown Chicago.
And now, rule time: Lou Manalti’s – You are not visiting Chicago without having their famed deep-dish pizza – it’s a rule, I made it up a long time ago. Gosh I was so hungry the night I sat down and GORGED on a GORGEOUS deep-dish pizza with a side of excellent service. Damn, it was satisfying. Lord I love Chicago deep dish. Go to Lou’s. Order the deep-dish. This rule is not meant to break.
Side-trip: To use Toronto as comparison point again, the Chicago district of Andersonville reminded me of Leslieville, the neighbourhood in TO gentrified greatly, as is often the case (just ask Richard Florida,) by LGBTQ+ people, who seem to instinctively (and probably annoyingly) know when an seemingly undesirable ‘hood is actually teeming with potential, set up residence (as I did back in Leslieville in 1999 – the house I bought then for $250k and later sold was recently listed for $1.1 million!) This then attracts businesses and restaurants to serve them, most with just the right amount of chic and edge required to make a good impression on a gaybourhood now alive and thriving. This then makes said neighbourhood a hotspot; the mainstream follows, as is their wont.
That is pretty much lovely Andersonville, know for it’s diversity, queer-friendliness, women-owned businesses and spirit of community.
I was impressed by the W&CF bookstore, which stocks books by and about women, children’s books for all ages, and the best LGBTQ fiction and non-fiction (they’ll order a book for your outside their mandate, too.) The rainbow flags fly everywhere in Andersonville and if you spot me in a ball cap that reads “You’re Beautiful” (which you are) – that’s from the acclaimed artistic efforts of Matthew Hoffman, who began his art campaign with just 100 stickers in 2002; today there are multiple versions of the message even in sign form throughout the region – I got the chapeau in Andersonville. There’s a great men’s shop there too, Cowboy’s and Astronauts, carrying everything from sexy witty greeting cards to menswear, candles, and beautiful hand crafted jewellery. Boystown, the aforementioned Belmont & Halstead, is within walking distance and Andersonville itself just a 20 minute Uber from my hotel .
A Gay Must: The Legacy Walk, in Chicago’s “Boystown” is an outdoor public display celebrating LGBTQ+ contributions to world history and culture. Billed as “the world’s only outdoor museum walk and youth education program dedicated to combating anti-gay bullying by celebrating LGBT contributions to history.”
It is the world’s largest collection of bronze biographical memorials (35 presently) defining the nexus of Chicago’s queer community. Here, the lives and works of LGBTQ+ people, whose achievements changed the world but whose sexual orientation or gender were overlooked by history, are on proud display. New plaques are added each National Coming Out Day. Jane Adamms, Alvin Ailey, Josephine Baker, Leonard Bernstein, Keith Haring, Christine Jorgensen, Alfred Kinsey, Walt Whitman, and events like the Stonewall Riots and symbols such as the pink triangle make up this moving and fascinating wonderful idea. Every major city should have something like this.
Getting Around: Of course there’s Uber and taxi service but Windy City Limo is a great way to arrive in Chicago and get to where you want to be in style; ditto when it’s time to (sadly) leave.
Save On Seeing: A Chicago cityPASS is a great way to see five of the city’s major attractions – packaged together so you save significantly: 50%. It’s good for 9-days, has line bypass or expedited entry in many cases, and has mobile and paper options. Currently, a cityPASS is $150 CDN and allows you into Shedd Aquarium, Skydeck Chicago, Field Museum, Adler Planetarium, and the Museum of Science and Industry.
Classic Chicago: For the first time, despite many visits, I found myself front and centre at the world renowned Second City.
The cast of Algorithm Nation was so talented (their show which took aim at MAGA rallies, morning TV, white guilt, Black Twitter, modern sex, gun violence, and everything we can’t seem to escape from – including escape rooms – the women of the cast performing an improv’d pop song about astrological signs using those of audience members chosen as the song unfurled was a tour de force that left me gobsmacked), So good were these Second City-ers I embedded each of them in my mind because I know one day, at least one of these next-gen comics, will surely be LIVE… FROM NEW YORK CITY! IT’S SATURDAY NIGHT LIVE!
If you’ve not been to Chicago, don’t hesitate. If it’s been a while, you know it’s worth a reunion. Chicago has never let me down in two decades. It’s a city full of genuine, sophisticated people, who have a thirst for art and the new, and who are interested in you, too.
To compare it to another big city option, for me, New York City is great, but overrated. I liken NYC to a guy who describes himself online as a “hot sexy stud” but who ends up starfishing the whole time, marinating in its own gorgeous juices, while you pray a mate calls and interrupts your shag with the news that “something terrible has happened.”
Chicago on the other hand, is that hook-up who under-promised but so over-delivered that you don’t let them out the door without getting their number, a smile on your face long after your time together is over, however long the dalliance lasts, your phone turned off the whole time.
- Shaun Proulx, Publisher / Founder TheGayGuideNetwork.com
This trip, I was gifted again. Allen Schwartz is a fabulous Chicago greeter and I could not have been blessed with a more fun, engaging, funny, knowledgeable guide – we’ve stayed in touch since and he owes me lunch. Allen took me to Millennium Park, a $475 million gift to the city by the city that opened in 2004.
The 24.5 acre paradise within the Loop community area is home to a riveting piece of beauty, a bandshell designed by Canada’s own, Frank Gehry, though to call it a “bandshell” doesn’t feel like it does the spectacular creation any justice (see video below) and home to to Cloud Gate the famous “bean” sculpture by Anish Kapoor that draws millions to see it.
Random moment: Back to the lovely denizens of Chicago. While I didn’t make fast friends with this waitress, I almost proposed:
This visit, I found my favourite hotel in Chicago of all the times I’ve stayed here: Steamworks.
Kidding! The Blackstone Hotel is what I call hotel porn. (Not the Tommy Lee / Pamela Anderson rental type of porn, which, actually, I did watch once… in Chicago.) Hotel porn is when design and beauty intersect. When it has its own personality and point of view and is unlike any other “template” design found at many chains. When a hotel lobby (full transparency: I have a hotel lobby fetish) is so aesthetically pleasing and feels so joyful that you’d be happy to sleep right there (never mind with the actual room, whatever it may look like) on the animal print by the reception desk, head resting on a marabou pillow; when the space has an actual point of view, when risk is taken in the decor and humour is given permission to exist and when it (as is the case at The Blackstone Hotel) melds so beautiful with preserved aspects of a former glory, you get hotel porn.
The Blackstone is conveniently located on South Michigan Avenue, and their extraordinarily spacious rooms are chic and understated but luxurious at the same time, with views of Lake Michigan and Grant Park. When I stayed there, the rooms ran approximately $259.00 USD per night.
Notably, the staff err on the side of superbly courteous and authentically engaged. My first name is typically misspelled and my surname often unpronounceable to many, so I appreciated when Eric, who checked me in, took time to check the spelling and ask the pronunciation and proceeded to remember it and say it in greeting me whenever I saw him, which was often during the five days I was there. It’s the little things and I like it when forward-facing professionals are so good at what they do you remember them – and their name – months after.
So taken was I by The Blackstone Hotel, that I spoke with General Manager about its unique history (a dozen US presidents have stayed there,) the time a family returned an item they’d taken when visiting the hotel, and how it got to be so gorgeous, for a recent episode of my SiriusXM chat show after I was back home:
A Few Of My Chicagonian Things
Big And Baby Bites: Chicago has an embarrassment of riches when it comes to dining out, be it casual or a meal to remember. This time, I discovered a couple of fun ways to experience their infamous food scene, and if you’re in Chicago, there’s a rule you must follow at least once each visit.
Revival Food Hall – A collective of all-local restaurants under one roof covering 24,000 square feet, Revival allows you to sample either to-go or to eat-in in a communal setting some of the city’s acclaimed culinary scene. I chose Danke, and sampled the rustic fare found at their full-on restaurant, Table, Donkey and Stick (have you known a … more unique … name for a restaurant? Me neither.) I love this concept and the ability it gives you to try before you invest in a meal out – every city should do this. Or do a few of them!
Latinicity – Sort of like Revival but more focused. World-renowned Chef Richard Sandoval brings together 8 innovative kitchens, a full Mexican restaurant, cafe, bar and lounge, all under one roof to give you his tasty interpretation of Latin street food. It’s located in Block 37, a development located in the Loop community area of downtown Chicago.
And now, rule time: Lou Manalti’s – You are not visiting Chicago without having their famed deep-dish pizza – it’s a rule, I made it up a long time ago. Gosh I was so hungry the night I sat down and GORGED on a GORGEOUS deep-dish pizza with a side of excellent service. Damn, it was satisfying. Lord I love Chicago deep dish. Go to Lou’s. Order the deep-dish. This rule is not meant to break.
Side-trip: To use Toronto as comparison point again, the Chicago district of Andersonville reminded me of Leslieville, the neighbourhood in TO gentrified greatly, as is often the case (just ask Richard Florida,) by LGBTQ+ people, who seem to instinctively (and probably annoyingly) know when an seemingly undesirable ‘hood is actually teeming with potential, set up residence (as I did back in Leslieville in 1999 – the house I bought then for $250k and later sold was recently listed for $1.1 million!) This then attracts businesses and restaurants to serve them, most with just the right amount of chic and edge required to make a good impression on a gaybourhood now alive and thriving. This then makes said neighbourhood a hotspot; the mainstream follows, as is their wont.
That is pretty much lovely Andersonville, know for it’s diversity, queer-friendliness, women-owned businesses and spirit of community.
I was impressed by the W&CF bookstore, which stocks books by and about women, children’s books for all ages, and the best LGBTQ fiction and non-fiction (they’ll order a book for your outside their mandate, too.) The rainbow flags fly everywhere in Andersonville and if you spot me in a ball cap that reads “You’re Beautiful” (which you are) – that’s from the acclaimed artistic efforts of Matthew Hoffman, who began his art campaign with just 100 stickers in 2002; today there are multiple versions of the message even in sign form throughout the region – I got the chapeau in Andersonville. There’s a great men’s shop there too, Cowboy’s and Astronauts, carrying everything from sexy witty greeting cards to menswear, candles, and beautiful hand crafted jewellery. Boystown, the aforementioned Belmont & Halstead, is within walking distance and Andersonville itself just a 20 minute Uber from my hotel .
A Gay Must: The Legacy Walk, in Chicago’s “Boystown” is an outdoor public display celebrating LGBTQ+ contributions to world history and culture. Billed as “the world’s only outdoor museum walk and youth education program dedicated to combating anti-gay bullying by celebrating LGBT contributions to history.”
It is the world’s largest collection of bronze biographical memorials (35 presently) defining the nexus of Chicago’s queer community. Here, the lives and works of LGBTQ+ people, whose achievements changed the world but whose sexual orientation or gender were overlooked by history, are on proud display. New plaques are added each National Coming Out Day. Jane Adamms, Alvin Ailey, Josephine Baker, Leonard Bernstein, Keith Haring, Christine Jorgensen, Alfred Kinsey, Walt Whitman, and events like the Stonewall Riots and symbols such as the pink triangle make up this moving and fascinating wonderful idea. Every major city should have something like this.
Getting Around: Of course there’s Uber and taxi service but Windy City Limo is a great way to arrive in Chicago and get to where you want to be in style; ditto when it’s time to (sadly) leave.
Save On Seeing: A Chicago cityPASS is a great way to see five of the city’s major attractions – packaged together so you save significantly: 50%. It’s good for 9-days, has line bypass or expedited entry in many cases, and has mobile and paper options. Currently, a cityPASS is $150 CDN and allows you into Shedd Aquarium, Skydeck Chicago, Field Museum, Adler Planetarium, and the Museum of Science and Industry.
Classic Chicago: For the first time, despite many visits, I found myself front and centre at the world renowned Second City.
The cast of Algorithm Nation was so talented (their show which took aim at MAGA rallies, morning TV, white guilt, Black Twitter, modern sex, gun violence, and everything we can’t seem to escape from – including escape rooms – the women of the cast performing an improv’d pop song about astrological signs using those of audience members chosen as the song unfurled was a tour de force that left me gobsmacked), So good were these Second City-ers I embedded each of them in my mind because I know one day, at least one of these next-gen comics, will surely be LIVE… FROM NEW YORK CITY! IT’S SATURDAY NIGHT LIVE!
If you’ve not been to Chicago, don’t hesitate. If it’s been a while, you know it’s worth a reunion. Chicago has never let me down in two decades. It’s a city full of genuine, sophisticated people, who have a thirst for art and the new, and who are interested in you, too.
To compare it to another big city option, for me, New York City is great, but overrated. I liken NYC to a guy who describes himself online as a “hot sexy stud” but who ends up starfishing the whole time, marinating in its own gorgeous juices, while you pray a mate calls and interrupts your shag with the news that “something terrible has happened.”
Chicago on the other hand, is that hook-up who under-promised but so over-delivered that you don’t let them out the door without getting their number, a smile on your face long after your time together is over, however long the dalliance lasts, your phone turned off the whole time.
- Shaun Proulx, Publisher / Founder TheGayGuideNetwork.com
