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.
April 20-28, 2025: I’m visiting Chicago and looking for fun stuff to do! My time goes fast in this town, so reach out now if you’d like to make plans.

My name is Tyler and, damn, do I love Chicago. There arenāt lots of American cities that I look forward toāor suspect I could call homeāthe way I do with Chicago. Iāve 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. Thereās 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 Iām 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 doesnāt keep anybodyās secrets really, and if you look at whatās getting searched and where, itās easy to see folks are searching for stuff like gay escorts Chicago or ārentmen Chicagoā or āMintboys ORD.ā
Even if itās coded into stuff like male massage or m4m massage. Whatās 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 Chicagoās DGAF confidence about finding winter male escorts, or about anything else
If youāre headed to Chitown soon (or you already reside in this fantastic city), and youāre looking for a travel companion, Fly Me to You rates include my travel to and from, and itās easier than you might think to arrange a safe and discreet get together. Iām just waiting to hear from you.

P.S. I love this video series to give me a quick reminder of what Iām missing in cities like Chicago. Even if it isnāt technically about male escorts in Chicago, itās still worth a watch to help your imagination along with places we could spend our time together: