Chicago has come a long way from being just the "City in a Garden" to one of the largest cities in the Midwest. Known for being an architectural marvel, Chicago's city's lakefront allure and nightlife has attracted residents and tourists alike.
Your stay in Chicago around fine architecture and nightlife will be one comfortable stay. Adding affordability to it are Comfort Suites and TheWit - a Doubletree Hotel, the perfect choices for a Downtown Hotel.
Trump International Hotel & Tower Chicago is a four start hotel, affordable and comfortable.
Other great value hotels include Amalfi Hotel Chicago and The Carleton of Oak Park.
If, however, you feel like splurging on one of the top end hotels the following would be your best bet:
Four Seasons Hotel Chicago
http://www.fourseasons.com/chicagofs/
The Peninsula Chicago
http://www.peninsula.com/chicago/en/default.aspx
Belden Stratford Hotel
http://www.beldenstratford.com/
Conrad Hotel Chicago
http://conradhotels1.hilton.com/en/ch/hotels/index.do?ctyhocn=CHICICI
Dana Hotel & Spa
http://www.danahotelandspa.com/
If in for a musical retreat The Hard Rock Hotel Chicago would be your choice.
Chicago is renowned for its gastronomical delights and once here you cannot afford to miss the two regional specialities: its renowned deep-dish pizza and the Chicago style hot dog.
Be it a deep dish from the perpetually crowded Pizzeria Uno, the famous stuffed pizza from Giordano's or a ridiculously good hot dog from Hotdougs, you can never go wrong with any.
Fine dining Chicago restaurants include Charlie Trotter, one of the finest in the world.
Charlie Trotter
http://www.charlietrotters.com/
Places like North Pond(www.northpondrestaurant.com) and onesixtyblue(www.onesixtyblue.com) have a combination of delicious food and great ambience.
For vegetarian cuisine you have Karyn's On Green(http://www.karynsongreen.com/) and for a romantic dinner Geja's Cafe( http://www.gejascafe.com/) as the best options.