Pizzeria Portofino is an upscale pizza place right on the Chicago River serving bad Italian food and mediocre pies.

Sidetrack is an LGBTQ bar in Boystown with events all week long.

Aba is a sceney restaurant in the West Loop serving tasty Mediterranean small plates.

Gibsons Italia, in River West, is the trendy Italian sister spot to Gibsons Bar & Steakhouse.

Nico Osteria is a seafood-focused Italian restaurant in the Gold Coast’s Thompson Hotel.

Chicago Cut is a great steakhouse right on the river ideal for special occasions and power business meals.

Cindy’s has the best rooftop and views in Chicago that overlook Grant Park and Lake Michigan.

Roka Akor is a trendy Japanese restaurant in River North that has great food but is also expensive.

Public House is a good all-around bar in River North with solid food and plenty of TV’s.

Federales is a Mexican restaurant in the West Loop that's always a party. Go for a good time and eat some tacos if you're hungry.

Duck Duck Goat is a high-end Chinese restaurants that’s always fun with excellent and interesting food.

Great tacos often trumped by strange ordering restrictions and a crowd we'd rather not eat our Mexican food with.

Maple & Ash sits in the middle of the Chicago steakhouse Venn diagram. It’s both new-school and old.

Bill and Giuliana Rancic force us to like them with excellent Italian food in a trendy setting.

Bar Siena is great for a fun gathering in the West Loop. Go heavy on the pizza and pastas. And drinks. You’re going to want those too.

There’s no denying Big Star is an anchor tenant of the Wicker Park dining scene, but that doesn’t mean everyone feels the same way about it.