Best Time To Go
Chicago has a humid continental climate, and the city experiences four distinct seasons with extremely hot summers and cold, snowy winters. Summer temperatures often rise above 32 C (90 F), while a usual winter day offers little or no sunshine and a high of just below freezing. The peak season for tourists is from June to the end of August, it is a period packed with festivals and hot, humid days. The best time to go to Chicago for vacation is during the spring or fall, when you can bask in the sunshine and enjoy low humidity.
Transportation
Chicago has the famous "L," a system of elevated trains providing easy access to the city's many neighborhoods. The train is also the best way to explore the suburbs and visit nearby destinations like Milwaukee, another popular vacation idea on the shores of Lake Michigan. Public buses cover most areas missed by the "L" system, while taxis provide a convenient though rather expensive way for getting around downtown.
Food + Costs
You can eat in numerous restaurants around the city for less than $20. Chicago developed the deep dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying at least one.
Things To Do
Grant and Millennium Park
Located right downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. You can also find people playing chess out here and during the summer they have a lot of free concerts.
Shopping
Chicago is home to many, many places to go shopping. In the city core, you will find shops much like in New York down the city streets. The Nike store in Chicago is 3 floors!! If you are in Chicago, at least go check out the shopping!
Go To An Improv Show
Chicago is the birthplace of improv comedy and a visit to the city wouldn’t be complete without catching a show. Many of the huge comedians in the business now started out their days as a comedian in Chicago, probably at one point did Improv.
Navy Pier
The Ferris wheel provides a unique view of the city, but be prepared for the height and the speed... you go really high at the speed of a turtle. The top of the Ferris Wheel is one of the most perfect places for taking pictures of the city skyline. Be sure you pick a day to go when it is nice outside, otherwise you will be freezing and the ferris wheel may not be running!
Lincoln Park Zoo
Right in the middle of the city, you'll find a zoo! The zoo is a great place to spend the day walking on the wild side, and it's one of Chicago's top family destinations. Plus, did I mention that it's free?? Defiantly a spot to hit if you're in town and especially if you're on a budget!
Where To Stay
Hotels in Chicago can get expensive if the location is close to the city, but I highly recommend using AirBnb for your accommodations, not just in Chicago, but anywhere around the world! Airbnb is affordable and you also gain a contact who probably lives in Chicago, so they can tell you some tips and some secret gems in and around the city.