Chicago being the 3rd largest town in the United States has a lot to offer. Great architecture, food, beer, nightlife, music clubs, bars and so on.

There are two major observations decks of great interest. One of them is in the John Hancock Center which is on 875 N Michigan Ave. From the Observatory you get fantastic views of the city skyline and Lake Michigan. You can take a free multimedia tour which is narrated by David Schwimmer who is known as Ross on the sitcom “Friends”. It’s the 4th tallest building in Chicago, 7th tallest in the United States and one of the most spectacular of the city.

The skyscraper itself is also worth having a look at and a walk around. The building has 100 storeys and is 344 metres tall (1129 ft). The architecture is categorised as structural expressionism which is a style that emerged in the 1970s. It’s a branch of modernism where buildings display the structural elements both inside and out. Another great example of this style is the Hearst Magazine Building in New York City.

A lot of other great things are located on Michigan Avenue. North Michigan Avenue stretching from East Oak Street to the Chicago River is also known as the Magnificent Mile. There are plenty of opportunities to watch great architecture, shopping, dining and a night out on the town.

The Chicago Water Tower is an old landmark based at 806 N Michigan Avenue. It was the only building to survive the Great Chicago Fire back in 1871 in the burned zone. It was constructed in 1869, is 47 metres tall (154 ft) and the architectural style is neo-gothic and looks a bit like an old medieval castle.

Back in July 2011 a brilliant Marilyn Monroe statue called “Forever Marilyn” by artist Seward Johnson was placed on the Magnificent Mile. It was of Marilyn doing her classic pose holding down her dress due to air being blown up from a vent from the film “The Seven Year Itch”. The statue was removed in May 2012 which is a bit of a shame as it was really classy.  It can now be found in Palm Springs, California.

Several interesting buildings are located on the Magnificent Mile. A great example is the Wrigley Building which is located on 400-410 Michigan Avenue. It was designed by Charles Beersman and the style is a combination of French Renaissance and Spanish Revival with an American twist. The large clock tower is one of the building’s main features and the shape of the building itself was based upon the Giralda Tower of the Seville Cathedral. Another noticeable aspect is the walkway at the 14th floor connection the north and south sections.

Just opposite the Wrigley Building the Tribune Tower is located on 435 N Michigan Avenue. The architectural style is neo-Gothic and is the home of the Chicago Tribune who back in 1922 initiated an international design competition for their new headquarters. More than 260 entries were submitted and architects John Mead Howells and Raymond Hood won. The building was completed in 1925.

Around the corner at 401 N Wabash Avenue the Trump International Hotel and Tower is situated. This was planned to be the tallest building in the world back when the construction plans were presented but due to the 9/11 terrorist attack this decision was changed and when completed in 2009 it became the 2nd tallest skyscraper of Chicago. The building is a pyramidal class tower and you can get some really nice shots walking around it at ground level or if you’re on the river cruise. When being on Wabash Avenue south of the river you can get a great view and shot of the building too between the surrounding skyscrapers.

Also on the Near North Side based on the banks of the Chicago River, Marina City is located. The complex consists of twin towers which were completed in 1967, are 179 metres tall ( 587 ft) and each have 65 storeys. The buildings are corncob shaped and the style is classic modernist architecture of the 1960s. It’s used both for commercial and residential purposes. The bottom 19 floors of the towers is a spiral parking ramp, the 20th floor is for laundry and the 21st to 60th floor consists of units (apartments) which all stand out by not having any interior right angles and all living rooms and bedrooms have balconies. The complex has been used on several films. A noticeable one is Steve McQueen’s last film “The Hunter” where there was a car chase scene through the parking garage and the car ends up in the Chicago River.

Crossing the Chicago River from the Magnificent Mile you will be in the central area of town which is called The Loop. Going a bit further down Michigan Avenue you will have the great Millennium Park to your left. If you don’t feel like walking you can also take the train to the Randolph St. Metra Station which is located right next to the park.

Millennium Park is such a nice breathing space of the city. Here the Jay Pritzker Pavilion is located which is a concert venue designed by famed Canadian architect Frank Gehry. The style of architecture is deconstructivism which is defined by really pushing the envelope where structures look more like sculptures than buildings. You can have a stroll around the pavilion and like many of Gehry’s other structures the look completely changes from all sorts of angles. At the same time you’ll have great views of the amazing skyline as well.

Just next to the Jay Pritzker Pavilion you will find Cloud Gate (pictured below) which is an cool sculpture created by Anish Kapoor. Understandably it is normally very crowded around the sculpture. The surface reflects everything around it so you can get interesting pictures of yourself, your mates and especially the city skyline many different angles.

Right next to Could Gate, a video sculpture by Jaume Plensa called Crown Fountain is located. It’s also very crowded around this area which is popular among kids and families. The sculpture itself also serves as a fountain spouting water and has a waterfall down the structure as well which especially kids like to have fun with. Being a video sculpture the front display changes from time to time.

Chicago is known for having some great blues clubs.

The House of Blues is located on 329 N Dearborn Street in the lower part of the Near North Side. The House of Blues has clubs in different parts of the country and can be a bit different from town to town even though they are based on the same concept. In Chicago there’s a big concert venue but also a small bar and restaurant area known as “Crossroads” with really good live music by smaller bands. There’s a great atmosphere sitting here having dinner and a good craft beer.

Another cool blues club is Buddy Guy’s Legends on 700 S Wabash Avenue located in the Loop. It’s owned by Buddy Guy, was opened in 1989, and it is said that if Buddy is in town he can normally be spotted in the bar area. Furthermore he performs every January and his shows sell out fast. Other than that if you go to the club you can have drinks and dinner and watch great local bands like at the House of Blues.

Yet another great blues club with more of a local feel to it is Kingston Mines which can be found on 2548 N Halsted Street in neighbourhood Lincoln Park. In this club they have dueling stages which is very convenient because when the band on one stage is finished the next band starts on the other stage. Also here you can listen to the music having a craft beer and a meal as well.

The Loop is the downtown area of town where you will find a lot of interesting sights. If you are into hockey the Chicago Blackhawks has their official merchandise shore on 325 N Michigan Avenue.

The legendary Chicago Theatre is found on 175 N State Street which is a beautiful historic building famous for the classic vertical Chicago sign among other things. The architectural style is neo-baroque/neoclassical and it’s seven storeys tall.

Furthermore you will find a lot of interesting skyscrapers and a really fascinating one of its kind is simple known as Aqua due to a wavy structure. It is located on 225 North Columbus Drive, is 261.8 metres tall (859 ft) and has 82 storeys. It is categorised as modernist architecture and has got irregular balconies which creates a look of water flowing down.

Not too far from here the AON Center is based at 200 E Randolph Street which is the 3rd tallest building in Chicago with its 346 metres (1,136 ft) and 83 storeys.

A skyscraper that really stands out is the CNA Plaza (pictured below) which is a bright red 44-story tall skyscraper, 183 metres tall (600 ft), located on 333 South Wabash Avenue. The colour really makes the pretty ordinary piece of architecture stand out in the skyline.

The Chase Tower located on 10 South Dearborn Street is a pretty unique building due to its curvy shape. The reason behind this design was the bank’s need to have enough room on the ground floor to conduct the daily transactions while the executives needed high-placed office space in the tower portion of the building hence the downward slope. The structure has 60 storeys and is 259 metres tall (850 ft). The Exelon Plaza, at the base of the building, is a cool like spot to have a stroll around as well where there’s an exhibition of murals. Another interesting piece of information with regard to this building is that this is where President Barack Obama and First Lady Michelle Obama met each other.

There is actually similar curved building in Manhattan, New York City on 6th Avenue and 42nd Street called W.R. Grace Building which is worth having a look at too.

If you want to do walking tours of Chicago there are several options.

Chicago Architecture Foundation has several tours all focusing on different parts of town or on various aspects of the city’s architecture. It could be on the Aqua Building and Lakeshore East, Downtown Deco, Modern Skyscrapers, a tour focusing on Chicago as a film location and so on. There are a lot of options. On the tours you get some useful information on the history of the buildings and on the architectural aspects

Another great tour operator is Chicago Detours. They have interesting tours which are a bit off the beaten track. One used to be called “Inside the Loop” but browsing through there website it seems this particular tour has been changed to “Loop Interior Architecture Walking Tour”.

An absolute must is visiting the Willis Tower which was formerly known as the Sears Tower. Until recently this was the tallest building in the United States until it was surpassed by the One World Trade Center Skyscraper in New York City in 2014. It was also the tallest building in the world from 1973 to 1998. Willis Tower is located at 233 S Wacker Drive, has 108 storeys and it 442 metres tall (1,451 ft). The design of the structure is pyramidal and setback which gives it a really neat look. The structural engineer Khan actually invented a new tube concept which is called the bundled tube structural system. This is structurally and financially efficient and provided more space. It was a revolution within architecture and most buildings over 40-storeys built since the 1960’s use a tube design influenced by this concept.

Going up to the observatory called the Skydeck can take some time due to the amount of people visiting and the security but it is definitely worth the wait. It is a lot busier here that at the observation deck at the John Hancock Building. The Skydeck is located on the 103rd floor and you will have perfect views of the city skyline, Lake Michigan and the surrounding areas from here. A cool feature are the three glass balconies where you can stand above the glass floor 412 metres (1,353 ft) above the city.

Taking a cruise on the Chicago River and Lake Michigan is highly recommended. The Chicago River is a system of rivers and canals running through the city which gives it a bit of a Venice feel. It also divides certain parts of the town like the Near North from the Loop which is connected by bridges. Doing the cruise you will get some wonderful views of buildings, skyscrapers and the skyline in general from different angles both from the river and Lake.

Navy Pier is located on the Near North Side on the shore of Lake Michigan. It was built in 1916 to serve as a cargo facility but was also designed as docking space for excursion steamers. Today it’s the most visited tourist attraction in town and filled with loads of entertainment options such as museums, activities, shops and restaurants. One of the major attractions is the 45.7 metre tall (150 ft) ferris wheel. From the pier there are some great views of the city skyline and Lake Michigan as well.

Not too far from Navy Pier walking a bit further north up Ohio Street you will find a little nice spot called Ohio Street Beach. Passing this area going even further north up the shore line on N Lake Shore Drive you will get great views of both Lake Michigan, the city skyline and noticeably of the John Hancock Center.

At S Riverside Plaza you will find Union Station which has been used in movies over the years but probably one of the most classic scenes is from the Brian de Palma directed film “The Untouchables” from 1987 with Kevin Costner, Sean Connery, Andy Garcia and Robert de Niro. The classic scene was filmed at one of the grand staircases where Costner is in a gun fight with mobsters and mother’s baby carriage is rolling down the stairs. During the gun crossfire Costner runs down that stairs to save the baby and is helped by Garcia who jumps in front of the carriage at the bottom of the stairs and stops it from tripping over.

Goose Island Brewing Company is a local craft brewery situated at 1800 N Clybourn Avenue also in the Lincoln Park neighbourhood. Tours of the brewery are conducted on Saturdays and Sundays if you fancy that. Right next to the brewery they have a cosy little restaurant/pub which serves their beer and really good pub food as well. The steak sandwich is highly recommended. Even though Goose Island is now owned by Anheuser-Busch they still make the same good quality beer as they did before they acquired the company.

If you are into beer there are some great beer tours of different areas of town. The company called Chicago Beer Experience has a great tour of some really cool spots in the Lakeview and Lincoln Park area. The tour is called “Lakeview & Lincoln Park Beer Tasting and Bar Tour”. A couple of the highlights are visits to a specialty beer & wine store and a beer & bacon bar where you will get beer tasters which pair with bacon. This is good fun, you’ll get an insight to the history of Chicago beer, taste some different & great beer and you’ll get to meet some cool people with the same interest as you – highly recommended.

A bit of an alternative neighbourhood of town is called Pilsen on the Lower West Side. This area was originally populated by Irish and German immigrats and later by Czechs from Plzen in present day Czech Republic. It is famous for all the murals dominating the townscape. A fair bit of these will be found along 18th Street and down the side streets from here. A lot of this is really great art.

One of the greatest attractions of Chicago is actually a bit of a hidden gem which is the University of Chicago. It’s located in the neighbourhood Hyde Park which is about 11 km (7 miles) south of downtown. It’s a beautiful campus with a lot great architecture, many in different variations of gothic styles. The campus is huge and covers 85.4 hectares (211 acres).

The Chicago Transit Authority (CTA) is the operator of mass transit in Chicago. The trains of the Chicago ‘L’ (“L” or “El” is short for elevated) is a part of the system and they cover big parts of Chicago. In the city centre a train station will always be within walking distance. The best way of exploring is by foot due to the size of the city using the train system is a great and efficient option.

An interesting story about the name is, that the original name of the band Chicago was The Chicago Transit Authority. But when the CTA threatened with a lawsuit they changed the name to simply Chicago.