Chicago is a vibrant cosmopolitan city with lots of attractions and entertainment for tourists and is a huge lure and should be included in your traveling agenda. It is located on the shore of the Great Lakes and has marvelous landscapes and nature. The cultural scene of the city is exciting and has plenty of dining, music, and theater options for you to try. The city is iconic and one of the most recognizable places in the country. You can easily find something entertaining in Chicago, however, if you want to truly make the most of your visit, you can consider visiting some of the tours and attractions at night.

Willis Tower Skydeck

Willis Tower Skydeck is one of the top attractions in the city, and it used to be the highest building in the Western hemisphere. The Skydeck provides amazing views of the city and it is open till 10 pm. Moreover, there is a bar that is open till midnight. The Willis Tower Skydeck is the perfect place and for those under 25, a car rental can give the opportunity to have a great night in the city.

Take a Mob or Crime Tour


If you want to learn more about the mob history of the city you can join the mob or crime tour. Some of the tours are held in the evening and at night, so you will easily fit them into your itinerary. There are walking tours, and scavenger hunts and if you rent a car you can embark on a driving tour.

Lincoln Park Zoo

Lincoln Park Zoo is a great place to visit for the whole family but on Fridays, there are special events for adults only. The events vary from week to week and normally involve alcohol, so you are bound to really enjoy this night in the city.

360 Chicago

Сar rental in Chicago under 25 with  is a great choice if you want to drive to 360 Chicago, located in John Hancock Center. Not only does it have amazing views of the Great Lakes, but also a perfect overview of the city, since this observation deck is located on the 94th floor, thus if you get there at sunset, you will truly enjoy the best sights of the city.

Go on a Dining Tour

Chicago has lots of restaurants, cafes, and bars, so if you want to experience its multinational cuisine and find some unique tastes, you should join one of the dining tours of the city. You can choose to focus on one specific type of cuisine, like say Greek or Italian, or opt for the multiethnic experience and set out on the culinary adventure.

Visit a Comedy Show


Once you are in Chicago you should not miss the opportunity to see a comedy show. Try to get tickets to standup shows in Second City or Annoyance Theater, as you will be able to have a good laugh, and maybe see some unique local talents or even some celebrities. It is a great way to spend the night in the city and unwind, so it will definitely be a must on your travel itinerary.

Adler Planetarium

Adler is another staple in the city tour, and fortunately, it is open to the public late on Wednesdays. There are shows organized and lots of other entertaining and educational activities. It is great for the whole family as everyone will enjoy learning about the universe, but it is mandatory to book the tickets online in advance, so be sure to do that if you want to visit Adler Planetarium. So even if you don’t get to see stars in Chicago due to light pollution, you will have a wonderful experience in Adler.

Navy Pier

This location is a must on your Chicago itinerary, besides it has lots of activities to offer during the day and at night. Moreover, the city looks completely different, but even more mesmerizing at night time, so if you are up to it, you should check out Navy Pier at night. There you will try lots of rides, and games, visit some local bars or cafes and of course, you ought to check out the huge Ferris Wheel located there.

River Cruise

If you are trying to plan an unforgettable experience in the city, you must try going on a river cruise in the evening or at night. The views of the night city are nothing less than spectacular. Plus you get to see it from a totally different perspective. There are different cruises to choose from, some offer dinners and others dancing, but you are bound to have a great time if you choose this pastime.

Digital Art


Another must in the city is the Art on theMart. It is a huge projection of the art pieces on the wall of theMart. It takes about 30 minutes and looks breathtakingly beautiful over the river. Even if you don’t enjoy art that much, you still should try and check out this location in the night city. If you get a rental car for young drivers, you can make it into one of the stops on your driving tour around Chicago.

The city is full of exciting places, and even if you do not have lots of specific points on your itinerary, you are bound to stumble across some of the sights wandering around Chicago.