Q&A: When is the best time of the year to travel to Chicago?
Question by floridagirl: When is the best time of the year to travel to Chicago?
I want to find the cheapest tickets and best weather to travel to Chicago. Weekends, weekdays, holidays, etc. it doesn’t matter when.
Best answer:
Answer by bigd
seeing that your name is floridagirl i would say DONT go when it is cold!! the wind chill and the snow would be really bad.. heck when i was there in august i had to buy a long sleave shirt cause the wind was making me cold (yes i am from fl and get cold very easy)
august was a good time to go cause it is warm enough you can walk around easy and you can do things like boat tours which would not be available in the winter.
have lots of fun, we did so much in one weekend it was crazy! be sure to go to the green mill bar, it is great and has been around sense the 1920′s it used to be a speakeasy where all the gangsters drank! it has been in lots of films too.
What do you think? Answer below!

Summer.
Anytime of year you can find decent deals…
Flying into Midway airport is usually cheaper, and is a closer taxi ride to downtown hotels…
If you are from Florida, I would personally recommend traveling here in July or August as it can be chilly otherwise…
I live in Chicago so I say the best time to come here is in July or August
i live in Chicago so summer.
there are all kind of festal in the summer.
check the chicago web site.
Definitely come in the summer when there are festivals and free concerts in Millenium Park nearly every weekend. Although the wind can make it ‘chilly’ occasionally, I would suggest coming in mid or late June as opposed to sweltering July or August. Last summer there were quite a few days where the temp topped out at something like 103 degrees; tolerable at the beach but if you’re planning on shopping and cruising the streets the boiling-hot pavement is enough to induce heatstroke.