Beer Bistro (1061 W. Madison)- great place to grab a drink and great food. My favorites are the tatar tots, tomato bisque, pizza, and hummus plate (if I am feeling healthy)
http://www.thebeerbistro.com/ P.S.- free shuttle to all United Center sporting events
Two Sisters Boutique- http://www.shop2sisters.com/ (1167 W. Madison)- everything in the store is under $200 and most things are well under that price. I have found great jewelry and scarves here.
Sushi Wabi- 842 W. Randolph (http://www.sushiwabi.com/)- right in the heart of the amazing restaurants on Randolph, this sushi place is wonderful and unassuming. Its pretty small and cozy on the inside, but allows for you to just focus on food and conversation.
Fix Chicago-1101 W. Fulton St. (http://www.shopfixchicago.com/)- new to me, this boutique carries some upscale brands and unique styles, definitely a hidden gem
Meli Cafe and Juice Bar- 301 S. Halsted (http://www.melicafe.com/)- AMAZING breakfasts in greektown with fresh smoothies or juice options. Usually a line in the morning, but it moves fast and you will love your brunch/breakfast.
Bess and Loie- http://www.bessandloie.com/ (1015 W. Lake)- all types of accessories are found here like purses, clutches, and jewelry. Everything is really different from anything you will see anywhere else in Chicago
Smitten- http://www.smittenboutique.net/ - 1041 W. Madison - Best place for engagement/shower/bachelorette gifts. They also have some baby gifts and help with wedding planning.
The Fig Tree - 1037 W. Madison http://www.thefigtreechicago.com/ -Best place for any type of gift (baby, birthday, wedding, friend, etc) They also carry a lot of cute jewelry and seasonal decor.