Yes, I live in a suburb of Chicago so I am a little biased about the City of Broad Shoulders. Chicago has been the backdrop for many historical events. Just like New York City, Chicago had its own group of gangsters. The "Chicago Outfit" was at one time led by the infamous Al Capone. Race Riots and the 1968 Democratic Convention sparked other kinds of violence in Chicago. However just like any other large urban city, through the dark marks in Chicago's history shine many wonderful aspects.
Chicago is bursting with culture. One can visit Greektown, Little Italy, Chinatown and Ukrainian Village without leaving the city. There are also other ethnic enclaves that include Polish, Puerto Rican, and German heritages. I would highly recommend visiting an ethnic area during a visit to Chicago. The most popular tourist attractions include Navy Pier, The Field Museum, The Art Institute, and The Museum of Science and Industry. Plus, Chicago boasts Championship sports teams along with biking, boating, and ice skating.
One of my favorite times in Chicago is when the "Magnificent Mile", also known as the Michigan Avenue area, is having its tulips days in the spring. There are so many beautiful colors and I see photographers on a daily basis snapping away.
Here are a few of my own Chicago tulip photos.
I do have these photos posted on my other blog, Chicago Daily. I started that blog a couple years ago and have slowed down on it as I've started this new blog.
As far as vacationing in Chicago, really any time of year is great to visit. For first time visitors, Chicago in early summer or early fall are my favorite times of year. Mid-summer is wonderful for the beach but as we've seen this summer, can sometimes get uncomfortably hot. Winters in Chicago are full of beautiful Christmas decorations and Thanksgiving parades but can be extremely cold.
For accommodations, some hotels run seasonal specials. I have also seen some good Chicago hotel deals on sites like Groupon and Living Social. Areas like Michigan Avenue tend to have higher prices across the board as far as food, accommodations, and activities. Navy Pier is free to walk around but Imax Theater ticket prices run around $18 a ticket and Ferris Wheel ticket prices are $6 per person. Other fun free activities include walking around Millennium Park, checking out The Bean, and visiting the Lincoln Park Zoo. http://www.choosechicago.com/ has a "Deals" section that is worth checking out.
All in all, this "Second City" is a wonderful place to visit no matter what time of year you come. Carpe Diem....book your trip to Chicago!