Top 5 Stylish Places for an Upscale Date in Chicago

There’s something about her that makes you want to be better? If this special lady in your life is the embodiment of class and style, then she absolutely deserves a man who’s ready, willing, and able to take the relationship to a whole other level. Or to begin with, to take her on one proper upscale date.

But before you book a table at one of these stylish places, there’s something else you must do.

Prepare your crispest shirt, pay a visit to your barber in downtown Chicago, and grab some chocolate and flowers. You’ll want to be at the top of your game, so dust off your old etiquette book and learn some well-mannered tricks to impress her with. If anything else, it will boost your dusty confidence.

  1. Prosecco

Regardless of what anyone tells you, there’s only one universal truth – when it comes to first dates and exceptional ladies, nothing beats a fancy Italian restaurant. This one is located in River North and is a nice mix of traditional and modern, with the most delicious orecchiette tartufo you’ll ever taste.

  1. Boka

Your date will fall in love with Linkon Park’s Boka for its incredible beef tartare and suave ambient, and you’ll find it equally seductive because this stylish restaurant surprisingly won’t burn your pocket. Take a walk to the Alfred Caldwell Lily Pond after dinner, the best Chicago spot for a first kiss.

  1. Piccolo Sogno

Piccolo Sogno is another Italian restaurant that is ideal for your Chicago date. Unlike Prosecco, which is super-elegant and ritzy, this one is best described as charming. Book a candlelit table for two at the garden patio, split a homemade pasta in a cozy atmosphere, and get tipsy from love and Italian wine.

  1. Bavette’s Bar & Boeuf

Bavette’s Bar & Boeuf is not only romantic and classy; just like your dream girl, it’s also intriguing and sexy. Prohibition-themed, this intimate little bar feels very mysterious, which makes it a perfect spot for getting to know each other away from prying eyes. Share a mango sorbet before you kiss.

  1. Celeste

When in doubt, go to Celeste! This incredible dining spot is actually three restaurants in one, with every floor offering a slightly different menu in a completely different ambient. For the first date, book a table on the second floor, which is a private but glamourous Great Gatsby-style Deco Room.

Bon appétit and good luck!

About Author: The author of this blog is a content marketer who formally worked at Emerging NewsHub 24. A writer by day and a reader by night, he loathes discussing himself in the third person but can be persuaded to do so from time to time.

Post Author: Clare Louise