Home is where the heart is. I grew up in Chicago and though I have been away now for over 25 years, it still feels like home every time I go back. At the same time, our current house, where we have lived for the past 25 years, is just as much my home. For the first time in many years, we are not traveling over Thanksgiving. We are staying at home and staying safe and that is something I am quite thankful for at this time. What are you thankful for today?
Here is a list of my 25 top things to do on a Chicago 4 day itinerary (though I suggest spending more time in my favorite city if you can).
Frank Sinatra said it best when he sang “My Kind of town Chicago is”. If you are planning a first trip to the “Windy City”, there are a wide range of sights and things to do in Chicago for all interests. Here is my list of top 25 Chicago attractions in my favorite city.
The best Chicago street art comes in many forms – and it is free.
Growing up in Chicago I used to spend my teenage summers hanging out along the lakeshore, biking swimming and sunning. Sometimes I would spend my day at one of the many sandy beaches, but more often than not, I would just bike the length of the rocks along the lakefront. Those large limestone blocks were put in place in the early part of the 20th century to prevent erosion but they eventually became a canvas for local want-to-be artists who covered them with cans of spray paint and multi colored paint brushes. This was the Chicago street art of my youth.
Chicago winters get a bad rap. Yes, Chicago is called the “Windy City” for a reason, and winters there do still get snowy and cold. But like everywhere else in the world, global warming has had its impact here as well, and Chicago winters are nowhere near as frigid as they were when I grew up there in the 70’s and 80’s. If you are looking to visit Chicago on a budget, then consider a winter weekend break in my favorite city as your best option.
This is my favorite view of Chicago. This is the view I grew up with. As a teenager I used to bike from my house to the lake and along the lakeshore all summer long. Today the parkland along the lake is as popular as ever – even more so as millions of annual tourists also take advantage of the 19 mile Lakefront Trail. Don’t have a bike? Not a problem. Bike rental kiosks are located troughout the city and are popular with locals and visitors alike.
This post was recognized by the North American Travel Journalists Association (NATJA) with a Silver journalism in travel excellence award in 2020 in the category Photography – Portrait, People
The glass box called “The Ledge” is a popular selfie photo spot on the 103rd floor Skydeck of the Willis Tower in Chicago. Stand, jump or lay on the clear glass floor and look down 1353 feet to the street below. Would you do it?
Chicago is a city of neighborhoods, each one with a distinctive personality and community. It is also a city with a very diverse ethnic population and it takes pride in that diversity and gets its strength from it. Where else would you see a Scottish bagpipe band marching in the annual Chinese New Year parade?