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Elite Male Escort Tyler DĂĄrlig Ulv

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Home » Chicago

Chicago escorts are nothing short of world class, and the fact that Rent.Men Chicago is always bursting at the fly with talent is a testament to that. 


September 10-23, 2022

UPDATE: My Chicago visit this time is fully committed. I’m beyond grateful for the generosity and enthusiasm this town has for showing me a good time. Ilu, Chi <3

So very nice the last time, I’m already ready for more. I have some very limited availability during this visit but would be so jazzed to make plans with you in Chicago as the Summer draws to a close. 🌬


rentmen chicago and gay escorts chicago always start the day with breakfast
Breakfast zoom meetings in Chicago

My name is Tyler and, damn, do I love Chicago. There aren’t lots of American cities that I look forward to—or suspect I could call home—the way I do with Chicago. I’ve had some incredible times, eaten some incredible meals, and met some completely incredible folks in my visits to the Windy City over the years.

While Berlin is home base these days, I still strive to get out to Chicago (whether I list it on Rentmen Chicago or not) a couple times each year. There’s nothing as good for my spirit as renting a comfy condo somewhere in Near North (cause you can just walk to all the fun stuff or to the lake) and plotting out how many trips to Steamworks Baths in Boystown I’m gonna get to make this visit. 

Being a male escort can be a time consuming job. But chances to unwind in Chicago with good friends make it so worth it.  Join my private email list now to receive personal updates and announcements about travel plans or trips to Chicago or nearby areas.

The Chicago Escort scene is always booming

Google doesn’t keep anybody’s secrets really, and if you look at what’s getting searched and where, it’s easy to see folks are searching for stuff like gay escorts Chicago or “rentmen Chicago” or “Mintboys ORD.”

Even if it’s coded into stuff like male massage or m4m massage. What’s funny is that Chicago escort searches seem to reliably spike right when those long hateful winters are in full swing. 

Eventually, I think Chicago will be the most beautiful great city left in the world.

Frank Lloyd Wright

I love Chicago’s DGAF confidence about finding winter male escorts, or about anything else 

If you’re headed to Chitown soon (or you already reside in this fantastic city), and you’re looking for a travel companion, Fly Me to You rates include my travel to and from, and it’s easier than you might think to arrange a safe and discreet get together. I’m just waiting to hear from you.

You wanna reach out? 

@tylerthebadwolf

P.S. I love this video series to give me a quick reminder of what I’m missing in cities like Chicago. Even if it isn’t technically about male escorts in Chicago, it’s still worth a watch to help your imagination along with places we could spend our time together:


How to become a male escort in Chicago?

This question gets searched a LOT, but one thing this site doesn’t do is provide instruction about being a gay or straight male escort.

If it is of interest to you, I encourage you to do as much research as possible before you make any decisions. I found Aaron Lawrence’s book to be extremely helpful (if now a little dated) when I was younger.

What do gay escorts cost in Chicago?

Escorts are often independent workers who set their own rates and make their own plans. If you have access to a site like Mintboys or Rentmen Chicago, I encourage you to do a pass, searching your ZIP code or neighborhood in Chicago to get an idea of average hourly rates. If you want to keep yourself safer online while you do that, I’ve got some best practices for information security available.

Best way to contact Chicago gay escorts?

Whatever way they say!

Seriously, always try to respect someone’s wishes about how they prefer to be contacted. I always discourage using messages on websites like Rentmen, because it’s impossible to know they’re safe or how they may be used against you later on.

Here’s how I prefer to be contacted (spoiler: it’s easy, encrypted, and free).

Will male escorts see someone on the DL?

I’m a believer that someone has the right to live how they want to live their life. It isn’t my place to say everybody has to be out and proud, or even identify as gay. A few years back I stopped asking folks about gay because what men get up to on their own time is their own business. Long as you treat someone with respect and follow the rules they’ve laid out for you, it shouldn’t matter if you’re straight, gay, bi, married, or anything else.

Is Tryst a reputable site to find male escorts?

Tryst is definitely growing and they do rank on google in some major cities like Chicago. Wherever you search for male escorts, you should be mindful to do your homework and don’t enter into any situations you don’t feel comfortable with. Tryst.link is as reputable as any other male escort site, and listings with verified stamps usually indicate someone is taking their work more seriously.

Read the full list of frequently asked questions here.

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