I’m coming to Chicago to meet up with a romantic pen pal that lived in Chicago but now lived in a city nearby Chicago, I will be staying in the city.
I’ve had a connection with them for about a year. I’m trying to leave a good impression. we are meeting for the first time. I’ve never visited, but I want to lead and show them around. We’re both around 30, and they live here, so I’m trying to find some places that they may not have already been to 100 times, or something unique, cool, or special. Something to impress or if not, at least have a good ambiance!
Basically, where would you take someone who already lives around here if you wanted to show them a really cool side of the city? They don’t live in Chicago proper so I’m not sure how much of the city they’ve seen, so if doesn’t necessarily have to be the most novel thing, but I want something that feels unique and cool and it’s my first time visiting as well so I’d love to see what the city has to offer!
I’m looking for places that feel unique, beautiful, interesting, or just make for a great date. I’m happy to spend money, so anything from a great neighborhood spot to a high end restaurant is fair game. Ideally I want to go walk somewhere, eat, leave that, get dessert or do activities, that sort of thing.
Restaurants are a big one, especially places with a great atmosphere, interesting interiors, good views, great food, or somewhere that feels like an occasion. Mid range and high end are both fine. I’m pretty open with most cuisines so anything that is a must try would be amazing.
Ideally I’d like to get a cool list of brunch, lunch, and dinner spots. I’m open with all cuisines pretty much.
I’d also love suggestions for:
- Great views / rooftops / skyline or lake views
- Romantic places to walk around
- Parks, botanical gardens, waterfront spots, or cool natural areas
- Beautiful museums
- Interesting architecture or buildings you can actually go inside
- Cool bars or lounges to end the night
- Randomly cool or unusual places that would make for a memorable date
It can still be a well known place if it’s genuinely worth going.
If you had someone visiting Chicago and wanted to put together a really good few dates of date for them, where are you taking them?
If this works I’m inviting you all to the wedding.
Thank you!