DiSotto Enoteca near North Side of Chicago (E. Chestnut St) is a wine bar for the discerning. Offering greate wines as well as food, it has been raved by many people who frequently visits this place. Its stunning decor is an ideal spot to bring your friends or loved ones, or date to have a great conversation over drinks. Folllow through with many nearby fine restaurants for a hearty meal.

Ch'ava Cafe on N. Clark, Chicago is a fairly new place and already has a good following by coffee and tea lovers alike. Internet access and online coupons drive people to this place for a friendly conversation with your friend or date over a hot cup of coffee. Nearby locations for evening entertainment, restaurants, dance clubs make this an ideal place.

Ten Cat Tavern is a dive bar with a difference, offering snooker and billiards it has attracted a loyal following since its grand opening in 1994. Plenty of lounge space to sit, chat and get to know each other like on a first time date. Make sure your date is warm to the environment because billiards may not be her cup of tea. Nevertheless a must place to visit to relax and have some activity at the same time.

Lincoln Karaoke in Lincoln Ave, Chicago has been pulling a crowd ever since its opened because of its almost unassuming appeal that brings people back to this joint time and time again. Perfect for going with a group or just checking it out with your date, but most of all its inescapable fun, because you never know what to expect!

In typical fashion Alinea on Halsted St. Lincoln Park, Chicago serves not only great food but a magical experience that one has to go once in their lifetimes. Superb decor and areas for dining like no other and costly but worth every penny. Make sure that you do some planning before visiting this place, so you can decide what to do when you get there. Ask your friends, relatives, boyfriends, girlfriends of what their experience was like here and you will get a good sense of what the place is all about. Unforgettable!

The Music Box Theatre on Southport Ave., Lakeview district of Chicago is a highly acclaimed movie theater that you can comfortably take your date and not be disappointed. The vintage interior is beautiful and has a charm about the whole place with a feeling of nostalgia. Take your loved one or date and then hit the town for nightlife activities of fun, dance and dinner.