10 Things to Do in Chicago at Night

Within the United States, Chicago is known as The Second City, because it has always been as important as New York, but in a way it has grown under its shadow. For this reason, its nightlife has created an identity just as interesting as that of the major cultural capitals of the planet and plans to see or do in Chicago abound in the morning, afternoon and also at night.

I invite you to continue reading this compilation of activities to get a more accurate idea of the things you could do on your trip after the sun drops below the horizon and the temperatures drop rapidly.

Can you imagine crossing Chicago in a barrel-shaped bus making stops to taste different types of beer in craft breweries?

The influence of beer on Chicago dates back to the 19th century, and not even the Prohibition of the 1920s was an impediment for the brewing of this drink to endure: under a façade of legal stores and stores, beer was brewed and sold clandestinely, and even today this drink is a hallmark of the Windy City.

Delicate flavors, others more forceful and even some extravagant. Among the beers you can taste on this original tour are the Dovetail Helles, the Metropolitan Flywheel or the Begyle Blonde Ale. Options for all tastes!

The Chicago River alone is one of the most visited spots in the entire city because of the many bridges that cross it from north to south to connect the section of the financial district that belongs to the Chicago Loop with the area that is known as the Near North Side.

That geographic importance has made it a favorite tourist destination when it comes to quiet, family-friendly plans to do at night in Chicago, so this is something that the city has used to its advantage with the creation of all kinds of nighttime tours on the waters of this very famous river.

Most Chicago night cruises on the Chicago River tend to last 1 hour at the most, since it is a relatively short stretch, although some offer dinner and live music and, consequently, their duration is much longer.

The food that is crowned the queen of local Chicago dining is undoubtedly the Deep Dish Pizza, a pizza that is prepared in a deep dish panwith several layers of mozzarella on top of the dough just below the sauce that would traditionally separate those two elements.

Throughout the city you will find pizzerias that offer a more traditionalist version of the Deep Dish Pizza as well as more innovative versions that incorporate other foods that are not historically associated with what is expected of this recipe with Italian origins.

However, Chicago food tours are an excellent option if you are looking to enjoy several establishments so that you can reach a verdict on which of all the restaurants you liked the most at the end of your trip.

Cities that are full of skyscrapers like Chicago offer a unique night scene because the streets are illuminated hundreds of meters upwards by the large number of lights that usually have these tall buildings.

At night you have the opportunity to see the city from another perspective with the night tours that are usually developed throughout the financial and tourist center of the city. Some are designed to be done pedestrian, while others are designed to be done in a vehicle, just like the best tour buses in Chicago: double-decker buses in which the second level is completely uncovered and are accompanied by a guide or an audio guide to understand the historical importance of the area being traveled.

In addition, many of these tours can also address very specific topics about this community, such as the stories of the mafias of the mid-century or tours that focus on enjoying the railroad history of the city.

The Chicago Cubs are the most important baseball team in this city and in its more than 150 years of history have become one of the cultural pillars of this community.

Their MLB games are played at Wrigley Field, an important stop on the itinerary of tourists interested in the sports culture of the destinations they visit.

The MLB regular season starts in early spring and ends in mid-fall, so if you are in town during some of these months it is highly recommended that you add a Chicago Cubs game to your evening plans in the Windy City, as games are usually played around 8 pm and can last 2 hours or even 2.5 hours.

Few cities have as strong a comedy presence as Chicago and without a doubt this city is the epicenter of entertainment within the English-speaking comedy industry.

Tina Fey, Steve Carell, Eugene Levy, Amy Pohler or Stephen Colbert are just some of the personalities who started their careers in comedy in Chicago, so it is an excellent idea to check out some of their nightly shows if you are looking for entertainment after sundown.

In this sense, a play that I recommend you not to miss if you feel like having a few laughs is a Shakespeare performance at The Lounge. It is a fun performance called "Drunk Shakespeare" in which the novels of the English writer are mixed with an improvised performance by an actor in a state of drunkenness. As you read it! You will have a very entertaining time with this theatrical work catalogued as one of the best in its field.

If you want to enjoy a spectacular night view during your visit to Chicago, you have plenty of alternatives.

The Ellis Tower, completed in 1974, was the tallest building in the world for a couple of years and for another full decade remained the tallest skyscraper in the United States. Today, with its Skydeck and glass cubicles, it remains one of the best options for enjoying the Windy City skyline.

• The observation deck is open every day of the week.
• Tickets can be reserved until 9 pm.
• During busy periods, such as summer or Christmas, there are special hours that extend until 10 or 11 pm.

Meanwhile, the 360 Observation Deck in Chicago is another ideal alternative for those who are looking to enjoy a spectacular night scenery more than 300 meters above this beautiful city and stands out for the degree of visibility so complete that offers its visitors.

• It is located at 875 North Michigan Avenue, formerly known as the John Hancock Center.
• On Fridays and Saturdays it remains open until 11 pm.

Boystown, also known as Northalsted, is the quintessential LGBT neighborhood within Chicago. Its historical significance is due to the fact that it functioned as a sort of social haven for the entire Midwestern community in the 1960s and 1970s.

As you can imagine, nightlife activities abound throughout this area that stretches north and south between W Grace Street and W Belmont Avenue. There are bars, coffee shops, nightclubs, trendy boutiques and a wide range of comedy clubs. If you find yourself on its streets you are always guaranteed to have fun.

The Annoyance Theatre is one of the most iconic comedy clubs in the city, but if you are in the area and the place is crowded you also have the option of visiting Trickery or the Laugh Factory. Keep in mind that any entertainment alternative in the neighborhood will be quite unique and in general this community stands out for the warmth with which tourists are received.

In many American cities it has been quite common for immigrant communities to form neighborhoods to reside and establish businesses under the aesthetic and community values they had in their countries of origin.

Chicago's Greektown is an excellent example and it is an area that to this day has maintained its essence and has all kinds of restaurants serving authentic Hellenic food. If you are looking for an entertaining and quality place to dine in Chicago, but want to go for a more unique experience, you can go to the Greektown for a cultural experience that unites America with the best of the Greek identity.

Chinatown is another immigrant community that is relatively close to Greektown. If you want to have a more extensive dining experience during your evening, you can also head south on I-90 and in less than 10 minutes without traffic you will be in another of the most interesting neighborhoods in the city.

Navy Pier is a stop you can't miss on your visit to Chicago if you really want to see the most important attractions of the city. In fact, it accumulates about 9 million visitors annually and nights are one of the best times to visit it because of the colorful lighting that characterizes it.

It is an excellent family plan that is included among the things to see and do in Chicago with children because of the existence of a Ferris wheel and other mechanized games such as a carousel.

If you visit you can't miss an authentic Chicago-style Hot Dog and I guarantee you'll also love the views it offers over the illuminated panorama of the city's waterfront over Lake Michigan in the dark of night.

Going out at night or going out during the day in Chicago are two virtually identical situations since there are no associated risks after sunset in a city with such a significantly high police presence.

The only recommendation I can give you is to keep in mind that the subway system closes its doors at about 1:30 am, to reopen at 4:00 am or 5:00 am on Sundays. Therefore, it is always a good idea to have cash to pay for a cab back to the hotel, although nowadays most cabs in the city have dataphones enabled for credit card payment.

Weather is another factor that you cannot fail to prioritize when going out at night in Chicago, since winters and autumns are characterized by being much colder than in other cities in the United States due to the incidence of wind in this region of the Great Lakes, so having a coat will be necessary, while in the summers it is preferable that you go out with breathable clothes due to the high temperatures of the day that can leave environmental sequels for the night.