Welcome to Chicago:
This is not really a story about what to see and do in Chicago. It is an attempt at getting you around this popular city without destroying your budget. As with most tourist meccas, Chicago offers plenty of easy ways to pay top dollar for things that won't really enhance your experience. Get a PopOut Street Map of Chicago.
When to Visit:
Chicago winters can be brutal, so pack accordingly. The weeks prior to Christmas are popular with Michigan Avenue shoppers. Be aware of the city's many festival and event dates, because fewer hotel rooms and higher prices can result. Book well in advance. Shop for low airfares to Chicago.
Where to Eat:
Sports legends Mike Ditka and the late Harry Caray are also known for excellent restaurants in the Windy City. Neither is exactly a "budget" offering, but they are unique Chicago experiences. Another great tradition is Chicago-style deep-dish pizza. Be warned: one or two pieces of deep-dish can be very filling. Go a size smaller than the conventional pizza you order at home.
Where to Stay:
Michigan Avenue offers fine shopping, dining, world-class museums and free shuttle buses to transport you between attractions. Hotel prices here tend to be high, but priceline.com and other discount Internet services often turn up good deals, albeit a block or two from the main drag. Hotel rooms near O'Hare Airport are often low-priced, but remember commutes to the center of the city can be an hour or longer at times. Four-star hotel for under $150/night: Hotel Felix at 111 W. Huron St.
Chicago offers one of America's best mass-transit systems, with subways in the "Loop" or downtown area, elevated trains (locals call them "the El") and buses. Lines serve both O'Hare and Midway airports, and are far cheaper than cab fare. It's customary and gracious to tip drivers of free shuttle buses in the Michigan Avenue area. If you'll be traveling in the Chicago suburbs, you'll need to rent a car.
Chicago Attractions and Nightlife:
CityPass offers admission to six Chicago attractions for $49 USD adult, $39 for children 3-11 years old. It's valid for nine days from first use. Rosa's Lounge on the north side is famous for jazz, but there are scores of clubs that offer the same. Check local listings for events during your visit. Chicago has a vibrant theatre community, with several Broadway-quality shows in town at any one time. The Second City troupe was a starting place for some of the nation's greatest comedy acts.
Grant Park on the lakefront was once a dirty railyard, but planners and philanthropists turned it into one of America's finest urban playgrounds. Concerts and festivals abound here, but it's worth a walk around even if nothing is scheduled. Don't miss Buckingham Fountain. The city's park system is one of the most extensive in the world.