Organizing a night on the Town of Chicago

Chicago is one of the biggest cities in the US and it offers a variety of fun activities to do at night.

There are many fascinating things to discover about the Windy City.

Tour by Foot

All through the city, you can view public art by Picasso, Chagall, Miró and other recognized artists.

One widely recommendable activity it’s a tour by foot of some of the main attractions and favorite food shops in the town.

You can embark on this experience with a guide and a group of people or just do your own list of the places you want to visit and go for it!

Sears Tower

The first stop should be the iconic skyscraper at Willis tower (old Sears Tower), where you can speed up to the Skydeck at 412 meters.

If being on the edge of a glass box on a 100 story building doesn’t give you a rush of adrenaline, I don’t know what will. The skyline from there is breathtaking.

Chicago Cultural Center

You can follow that by going to the Chicago Cultural Center, where there are more than 1,000 very diverse free exhibitions. You can catch music, seminars, dance, theater and film screenings, depending on the day.

Food Options

Another impressive quality of this grandiose city is that it could be America’s top food city. You can choose between the Italian beef sandwiches, deep-dish pizzas, hot dogs with seven toppings and a variety of international beers.

You’d be missing out if you didn’t try every single one of them.

Definitely, the smartest option for that is going to the largest food festival in the world, “Taste of Chicago“. Bring an appetite and try the local foods as well as the culinary creativity from around the world.

If you prefer a restaurant is recommendable that you taste the best Chicago style pizza at Giordano’s Pizzeria before you keep walking through the city until the next stop.

Walk on the streets, and if is chilly outside you can go under the Chicago Pedway system, which keeps you warm and safe from the cold.

Music Scene

To tap into the city’s jazz and blues heritage some of the go-to places are Buddy Guy’s Legends, where you can sometimes listen to the blues veteran and the other option is Kingston Mines in Lincoln Park.

You can find other 223 music venues in all.

From there you can lead to Millenial park, one of the main landmarks of the city. A good option would be sitting down in front of the Chicago River and just take in the beautiful scenery.

It is not rare to find a music festival in the near surroundings, where you can drink a beer and listen to talented local and international artists. Or dance the night away listening to the top DJs at the best nightclubs.

House music clubs are easy to find as they are scattered throughout the city, some of them subterranean. And most of them open 5 nights a week.

Bus Tours and Other Options

If walking or Ubering around the city isn’t good enough (such as for large groups) you can always opt for a bus tour.  Sight seeing tours in Chicago are available from companies such as Big Bus Tours, where you can hop on and hop off.  For your own private bus tours, you can contact bus charter companies such as Chicago Party Bus Pros.


All this and more makes Chicago many people’s favorite city in the world.  There is no shortage of stuff to do, so take some of the options above and make your visit a great one!