In order to enjoy your Chicago Illinois travel, it is best to consider the weather because it will determine the activities that will be available to you and how much you will pay for your accommodation. But this will depend on what kind of person you are since there are people who like indoor activities while others prefer outdoor. It will also depend on whether you enjoy being with many people or not.
With changing weather throughout the year, some periods may be too undesirable for you since it may either be too cold or too hot.
http://www.chicagotraveler.com/
http://www.highwayconditions.com/il.htm
1. Summer time
Summer time in Chicago attracts a lot of outdoor people because the weather at this time allows many outdoor activities. Since many people are likely to be there during the summer, accommodation costs tend to rise due to the high demand. For someone who prefers indoor activities, summer may not present a perfect vacation for you.
http://www.johnnyroadtrip.com/cities/chicago/index.htm
2. Autumn time
Autumn also sets a good time to travel to Chicago but a bit fairer compared to summer. Accommodation is not very expensive then since the number of people going there is reduced. If you plan for an autumn vacation, then you better be in Chicago between September and November.
3. Spring and winter
Spring and its kind of weather attracts people who like indoor activities but if you are on a tight budget vacation, then this is the best time for you too in terms of accommodation costs. Winter too has the same characteristic and although you could save a lot of vacation money, the rains and the snow will restrict winter sports only.
http://www.best-time-to-travel.com/Illinois/Chicago.htm#NOT
So make sure you utilize that well deserved Chicago Illinois travel vacation by checking the weather and being there at your best time.
http://www.lonelyplanet.com/usa/chicago/weather
http://travel.southwest.com/travel/weatherDetails.html?cityName=Chicago