1. Check out Chicago's rich architectural heritage by way of a Chicago Architecture Tour on the river.
The Chicago Architectural Foundation (224 S. Michigan Avenue; 312.922.3432) offers docent-led tours aboard the Chicago First Lady or the Chicago Little Lady. Purchase tickets at the Foundation office or before you board at the dock (Michigan Avenue and Wacker Drive).
The Magnificent Mile is home to over 400 internationally-renowned shops and boutiques. It is located on North Michigan Avenue between the Chicago River Bridge and Oak Street and is easily accessible by car, trolley, taxi, or bus.
3. Enjoy a drink at the Signature Lounge at the top of the John Hancock Building.
Located on the 96th floor of the John Hancock Building (875 N. Michigan Avenue; 312.787.7230) overlooking the Magnificent Mile, the Signature Lounge is an upscale bar offering breathtaking views of the Chicago skyline.
The Art Institute (111 S. Michigan Avenue, 312.443.3600) contains one of the world's finest art collections, with pieces covering the media spectrum. Check for discounts for children, seniors, educators, and AAA card holders. Open daily.
5. Enjoy one of the many Lake/River Cruises.
There are too many to name but most of the Lake/River Cruises are good and this is a fantastic way to take in this architecturaly magnificent city. Great for photography!
Wrigley Field (1060 W. Addison Street; 773.404.CUBS) is home to the famed Cubs, who haven't won a World Series championship since 1908. It is the second oldest ballpark in Major League Baseball. Tickets run between $14 to $60 per game.
7. Enjoy the Lincoln Park Zoo.
The Lincoln Park Zoo (2200 North Cannon Drive; ) is the nation's oldest zoo (founded in 1868) and indisputably the best bargain for parents in the United States. FREE. Open daily 9AM until 6PM.
8. Take the family to Navy Pier !!!
Navy Pier (600 E. Grand, on Lake Michigan; 800.595-PIER) is Chicago's number one tourist destination. This 3000-foot long pier was built during World War I and used in World War II to train the navy. Today, it is an entertainment megaplex complete with glass-enclosed garden, carnival rides, and food court.
9. Take a self-guided tour of the Frank Lloyd Wright Home and Studio.
Influential architect Frank Lloyd Wright lived and worked at his home studio, located in Oak Park (951 Chicago Avenue; 708.848.1976). The studio is open daily, and tickets range between $7-$10. Check for discounts for kids, seniors, AARP members and AAA cardholders.
Don't leave Chicago without enjoying a deep dish pizza (Chicago-style) from Giordano's or Lou Malnati's or Gino's Eat! These pizza pies will require a huge appetite and with their side and content will surely slow down even the most avid/experienced pizza lover! Also, near the Zoo, you can try the pizza pot pie at the Oven Grinder. Chicago is filled with incredible restaurants... but a trip to Chi-town without tasting their variety of deep dish pizza would seem incomplete.