I love Visiting Chicago, but have grown stale on the places I go and know. I tend to stay along/around the Magnificent Mile area, and up to now, it’s been great. But I know there is more available, so I began thinking. I want to hire an escort to take me on their ‘best date’ for a Saturday. I’ll pay, but I want to see places and do things that I haven’t done before. And I want it in the vein of her acting the part of a ‘hot GF’.  

Really, my goal is to learn more about places to go, things to do, etc when on a date.  

I’ve taken almost every woman I’ve been in a serious relationship with, to Chicago for a 3day weekend. I’m recently divorced and recognize she was the only one I didn’t take… because she said ‘I don’t like Chicago.’ Yes… should have been a major clue into where we’d go. But regardless. I’ve not been to Chicago on a ‘date’ for almost 10yrs.  

I contacted several Tour agencies, and was unfortunately up front with them. I had a 26yo tour guide who said she would set up a ‘day/date to remember’. THIS date was Not based on sex/interaction. I told her straight up I wanted to learn about Chicago so I could bring my date next time and know more things to do and places to go, than I do now. 12 hrs or so and I would pay her well (no sex/GF) just a straight tour for a cause. She was up for it.  

But the tour company read my email, and stopped the tour dead in its tracks. Lesson learned. Don’t give details until you have personal email access to the guide.  

Anyway, I am at a loss… but then it hit me. Find an Intelligent escort based/from in Chicago, to take me on the same date. And this way… I can get more for my money… although I know there would be a lot more $$$ involved.  

I’m looking to meet someone at 10am, coffee house in Intercontinental Hotel. Perhaps go upstairs for an hour, just to clear my head. Then I want her to take me on a ‘woman’s best all day date’ in Chicago. I’ll buy, but she needs to have a well thought out plan to meet my needs of learning some great things to do, when bringing a civilian woman back for a date. I want to end the day with a late dinner then return to the room for a tryst. I want GFE for the date, as if she was truly my GF for the day.  

Is this something I’m likely to succeed in finding?  
And how best to go about it?  
I don’t want to pay up front only to be ditched an hour in, because the $is in her purse.  
What should I ask and avoid?
Options, thoughts, recommendations?

I’d appreciate thoughts from both hobbyists and providers.

-- Modified on 5/16/2022 5:54:32 PM

Do that after you have already seen her as an escort.

Lol… what I WANT is made up, or at least has not occurred thus far. Hence I’m posting to find out options and thoughts.  

However the situation which leads me to this post, is very real.

That is a really good idea.

in this endeavor! There are lots of providers who love playing tour guide in their home city, especially once it starts getting warmer out. Most will have "clock free" half day or overnight dates where you spend half of the date out and about and the half behind closed doors (or whatever agreement y'all come up with). For a date of this length, the providers I know and would recommend (but can't because TER rules) in Chicago would most likely require a deposit to hold the date and then the remaining would be due at the start of the state. The likelihood of behind ditched an hour into the date is quite small so long as you mind your "p's & q's" (just be respectful and kind).

She's intelligent, brilliant really, well-read and a great conversationalist, and gorgeous and very stylish, with great taste.  She's not a Chicago native but has lived here a long time and knows the city well.  And the tryst, well, you will not be disappointed at all.

If I were in your situation and had the means, I would absolutely call Josie and tell her what you have in mind.  She does travel a fair bit, so make sure you can coordinate your schedules.  You'll not only have lots of ideas for future civilian dates, but you'll have a memorable day and evening.

She knows the niches in this city incredibly well. I've never played with her, but I've had the pleasure of interacting with her during provider hangouts and dinner. She's every bit as cool and genuinely friendly in person as she appears online.

This is a great idea, and I've lived in Chicagoland and would like to explore more as well.  I'll have to look into this.  Hope to hear back on how it turns out for  you.

wish i would’ve seen this months ago. i stay in mag mile/streeterville abs could’ve taken you on an amazing date and shown you many places around the city… oh well

I am available any time  your in chicago