1. Webster’s Wine Bar
If you are steadfast for Chardonnay, or if Chianti is your staple but you feel the nightlife doesn’t cut it, then Webster’s Wine Bar offers the relief you seek. Every month Webster’s chooses a feature wine, and tastings are organized accordingly. A few small tables create an intimate atmosphere for discussions. In the backroom or “library” old bookshelves line the walls and red velvet sofas give the room a burgundy study feel. The top floor is a larger room complete with fireplace. This room is generally booked weeknights for private functions, Monday nights usually feature live music, usually of the jazz genre. While the weeknight crowds tend to be mellow, the music is a far cry from quiet jazz. It’s more of a funky mix, with acid jazz overtones. 1480 W. Webster
2. Primehouse
Hotel dining brought sexy back in ‘06. Hip luxury, like that at the James Hotel’s new restaurant, David Burke’s Primehouse, replaced the button-down bore of yesteryear. Get your sexy on. Architect Deborah Berke has done a complete overhaul in the spacious dining room, featuring warm, rich tones of cumin and cinnamon. Unique design elements include ingrained wood flooring stained brown-blue, ‘’mother-of-pearl’’ plastered walls and blackened nickel chandeliers adorning the ceiling. Guests may settle into chocolate leather upholstered chairs complemented by red ‘’leather” upholstered tabletops.
616 N. Rush St.
3. Sports Monster
There is nothing scarey about Sports Monster in Chicago, in fact, just the opposite. It’s the thing to do if you are looking for the boys in the Windy City. Depending on the time of year, you can sign up for all sorts of classes/clinics and sports. From Biking to Rock Climbing to Running. Sports Monster may be a great pick to help you find an adventurous guy, who will make sure you are never bored!
4. Café Iberico Tapas Bar
The bar at Café Iberico is a great place for girls to order their sangria at the bar, and get invited to a table for some Spanish Tapas, located on 739 North LaSalle.
5. Join the Chicago Sport and Social Club’s Volleyball team:
Beach Volleyball in the summer
Indoor Volleyball in the winter
6. Montrose Harbor Dog Beach
Montrose Harbor Dog Beach located off Lakeshore Drive near Montrose, this place is packed with guys and their canines, particularly during the late spring and summer time
7. Old Chicago Watertower
This is a great place to meet guys who are either buying tickets for a show or are new to the area, perhaps they may need some directions!
8. Grant Park
Chicago Outdoor Film Festival on Butler Field [that is within Grant Park] bring a chair and join the guys who come in groups to see a flick.
Summer Dance Festival - 11 weeks of 1 hour of free dance lessons followed by two hours of music and dancing.
9. Chicago Millennium Park
1. McCormic Tribune Plaza, strap on your laces and take part in the ice skating which is sizzling from November 11th to March 16th.
2. In the spring and summer, Millennium Park is a great place to stroll the Chase Promende and take in a concert at the Pavilion.
