Ask anyone that lives here when the best time to come to Chicago is and they will tell you the Summer!
June-Septemberis the peak time of the year. This is when the city comes alive! You will find plenty to do during this time such as street festivals, food festivals, concerts, boat on the lake, beach parties, and so much more. Definitely take advantage of being on the beach, cruising on the river, and enjoying the beautiful weather at this time of year.
October-November is when it starts to get cold. It is a hit or miss whether it will be an Indian Summer or early Winter, but it is still a lovely time of year to visit. If you are a sports fan, Bears Football tailgates are huge at this time of year. Walking through the park to see the colorful trees is also a great treat.
December-March are definitely the coldest months of the year (they don't call it "Chiberia" for nothing). However, in December, the city comes alive with the beautiful holiday lights, carriage rides, and overall joyous spirit. It is a really beautiful time of year to see the city, so I recommend bearing the cold for a little to see the beautiful city lights.
April-May is a beautiful time because the city and it's people start to come out of hibernation from the cold winter. Weather permitting, people start to frequent restaurant patios and the lakefront a lot more during this time.
