The Fall and summer are the most ideal periods to plan your trip to the Windy City. Chicago offers a wide range of outdoor activities and special events during summer. The weather during this time of the year is muggy and crowds will be peaking too. For visitors looking to move around with lesser crowds, the autumn days are ideal. Winter days in Chicago are comfortable but you would potentially be deprived of much of the outdoor charm. Winter is also the time when you get cheapest hotel tariffs and the least waiting time at the attractions.
Best season to visit Chicago
http://www.expedia.com/daily/vacations/chicago/info/event-calendar.asp
Info for guaranteed excitement in Chicago
http://www.aboutalltravel.com/four-exciting-things-to-do-in-and-around-chicago/
For an "off the beaten path" experience visitors can consider the Chicago Food Planet which offers cultural walking and food tasting tours. Visitors are taken through the most historic and delicious streets of Chicago. The food tours also include lip smacking food tasting from ethnic eateries and specialty shops. The guided and narrated tours will help you gain an insider view of this great city, its treasured architecture, rich history and neighborhood restaurants. Reservations are recommended.
The 2 hour Segway tour is another way to enjoy Chicago in quick time. This tour is available to you by the day and night and the experience is truly exhilarating, unique and fun. Friendly tour guides will provide appropriate narrations throughout the tour.
Chicago offers a number of other exciting attractions and things to do. Depending on individual tastes and age profile you can draw up an itinerary that best answers your needs. The website below lists 30 of the top Chicago attractions with respective website URLs and contact information.
Top Chicago attractions
http://www.chicagotraveler.com/chicagos-largest-attractions.htm
Top 5 things to do in Chicago
http://travel.aol.com/articles/top-5-things-to-do-in-chicago