Haute Five: First Date Spots in Chicago

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So you met someone who you think may one day, possibly pan out to being someone you like enough to eventually be in a relationship with. But before you go jumping the gun, you have to actually go out first. This can pose a problem, living in Chicago there’s so much to do and so many places to go that finding the perfect first date spot can be daunting. Well have no fear, I have five great first date spots that are sure to impress on a first date and hopefully help to ensure a second.

1 Prasino (Rosemont)

Going out to dinner isn’t exactly a new idea when it comes to dating, but Prasino at the Fashion Outlets of Chicago in Rosemont has a couple different elements. First it gives you something to be right before or after, window shop at an excellent mall. Second it will be a major surprise to your date if they’ve never been there. Who would think that you could find such an amazing restaurant in a mall? Because Prasino not only has excellent food, but is committed to being green, so if your date is into the environment, you have a built-in talking point. And make sure you get one of the flatbreads as an appetizer, absolutely delicious.
5220 Fashion Outlet Way Rosemont, IL 60018 847-278-9900

2 Andy's Jazz Club

Andy’s is for the music lovers, especially those who love Jazz. It has a very cool ambience and the music is always amazing. They have live music there everyday starting at 5pm and it continues until at least 1am. I am against going to places where you can’t hear the other person talking, because the point of a first date is to listen and learn about one another, you can do this at Andy’s. Sit back, dine on some good music inspired grub and talk with an incredible Jazz-filled background.
11 East Hubbard Chicago, IL 60611 312-642-6805

3 Geja's Cafe

I can’t make a list of date-night spots and not mention what many consider the most romantic restaurant in the city, Geja’s Café. Now I know this is probably a little too romantic for a first date, but if you’re the overly romantic type then it could be perfect. It just celebrated it 48th anniversary, which means it has been a romantic date night mainstay in the city for a long time. This is fondue dining at its best so make sure you’re ready for decadent cheese and chocolate. There’s also their exclusive list of moderately priced wines, so you will have plenty of options of wine to sip on as you learn as much as you can about the person across from you.
340 West Armitage Chicago, IL 60614 773-281-9101

4 Bottle and Bottega

Instead of the traditional date-night spots, how about giving your date a memorable experience by adding a little creativity. At Bottle and Bottega they give guests a chance to hands-on art instruction with a glass of wine. You have a canvas, an art instructor and a glass of wine, perfect ingredients to create a night to remember. Once you sign up online, you arrive at the class and an artist will walk you through a piece of art to paint. You don’t have to paint what everyone else is painting though, you have the freedom to do whatever you want on the canvas, might I suggest trying to paint your date if your skills are up to par. I just think this is one of the cool things we have in the city and it’s a way to show a date that you aren’t boring and can think out of the box.
1241 S. Michigan (One of many Locations) Chicago, IL 60605 773-269-6570

5 Chicago Sunset Cruise

We live in Chicago, why not take advantage of the things we have that sets us apart from other cities. We have a magnificent skyline and Lake Michigan, so one of the best things to do on a first date is to combine these two beauties. How about a Wendella Sunset Cruise, which is a two-hour cruise that includes a brief narrated tour. It’s only available between May and December because, well, we live in Chicago, but it’s date perfection. It starts at the Wendella Dock at the Wrigley Building and the finale takes place at Buckingham Fountain for the start of the water and light display. Safe to say, your date will be impressed.
Wendella Corporate Office 405 North Wabash – P2E Chicago, IL 60611 312-337-1446
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