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The Windy City

Moving on to our next destination and base for the next five days after enjoying a great relaxing time in New Orleans, we arrive to the second largest city in the USA after New York: Chicago. On the shores of lake Michigan it’s this marvellous city, where the skyscraper was born. Many wrongly still believe it was in New York City where they were first erected but that’s not right. Referred to as The Windy City as the most known nickname, it’s not only because of the likely chance to be windy, but because of years back of political issues and rivalries with Cincinnati and the World’s Fair to mark the 400th Anniversary of Columbus arrival to America.

The city was once the 4th largest in the world, in time after the Great Fire of Chicago that destroyed most of the city in 1871, and thereafter rebuilt in record time with the new legislation in safety on buildings, broad avenues, beautiful landscaping and overall care and beautification. This was the time where the skyscraper was born, the first steel-frame structure in height in 1885 (the Home Insurance Building). Such a vast playground of empty plots to be built opened and unprecedented case in which architects from all over the world wanted to leave their work in Chicago. The architecture of the city is one of the finest collections of all styles. No wonder you can find here a school of architecture that has become a pride to the world, the Chicago School.

The elegant and expensive Michigan Avenue, known as the Magnificent Mile, is the heart of the city. Most of the city icons can be found along its length and it is intersected in the middle by the Chicago River, the next main attraction. Coupled with this, crossing through the centre of the city’s heart you have the Big L, or The Loop. These are the elevated subway trains. A sight on themselves either if riding them or capturing them from the street. And dotted here and there the remaining masterpiece, its buildings and extensive parks, with a fabulous lake front.

When calculating your time in the city do not underestimate. It is very large, with lots to see and do hence a minimum of 3 full days would be the best. Then considering how many other cities and places you can go in a short radius, then you’ll never run out of things to do. This was the example in this trip where we spared a day for Milwaukee, barely hour and a half north of Chicago along the Michigan Lake. It meant that in both occasions I’ve been to the city I’ve spent 3 days each time. The perfect number in order not to rush anything and enjoy at a quieter pace.

It’s one of the most walkable cities in North America, and one of the most pleasant that’s for sure. The wide avenues are often aligned with trees and gardens, and are spectacularly well design minding the attention to every detail, not to mention how clean this city is. While Western Avenue is the longest continuous street in the world; Michigan Avenue ranks the list among the world’s most expensive and beautiful. Countless statues, monuments and fountains complete the overall landscaping. So in truth, yes, you are in one of the most elegant cities in the world.

For the best skyline pictures go up the John Hancock Tower. Perhaps you remember this tower from Poltergeist, 3, the movie. It’s the second tallest in the city after the formerly named Sears Tower (now Willis Tower). They sell tickets for either one visit or “Sun and Moon”, which consist in two visits one in the morning and another in the evening. In reality, if you get there before sunset, you get to see both views for just one price, and it’s totally worth it doing this way. The night skyline is impressive with the infinite long avenues lighted up until your eyes can reach in the distance.

When coming to the next most important subject after sightseeing itself, that’s also one of the most pleasurable I have to say: food. As one of the biggest Polish nationality emigrants outside of Poland, expect to find great Polish food at many places offering among their specialties, the famous pierogi. The you have of course the impossible to miss option of a real Chicago Pizza! A must try indeed. Or how about a Chicago Hot Dog. Attention to the description: Beef (usually Vienna beef), on a poppy-seed bun, and topped with salad of mustard, diced tomatoes, a dill pickle spear, sport (chilli) peppers, a generous sprinkling of celery salt, diced onion, and a sweet-pickle relish. Feeling hungry now? A bright side, it’s very affordable city altogether.

For more information about Chicago check Wikipedia and Wikitravel sites. The United States of America currency is the Dollar (USD, $). Please note that any price reference is true as from when this guide was created, therefore check prices in advance as with the time they change.

What to see and do in Chicago

  • Gold Coast Towards the northeast of the city, right by the lake front is this up-scale neighbourhood with luxurious condo towers having incredible views of the city and lake.

-Oak Street Beach One of the most famous beaches in the lake with the most fascinating views towards the skyline behind.

  • Streeterville The next district south of Gold Coast and also along the lake front and parallel streets west from it up to Michigan Avenue, while to the south it limits with the Chicago River.

-Michigan Avenue It’s very advisable to walk from its starting point by the Drake Hotel towards the Millennium Park. This is, the Magnificent Mile, where the most impressive buildings are located, like the Hancock, Tribune and Wrigley Building.

-The Drake Hotel Facing the Oak Street Beach, it is one of the most prominent in the city for its luxurious since its construction in 1920.

-Palmolive Building Literally, the next after the Drake. One of the art-deco jewels in Chicago, tallest building when built in 1929.

Fourth Presbyterian Church of Chicago Built in 1912 in Gothic revival style. It is the second oldest structure in Michigan Avenue.

-John Hancock Center One of the architectural masterpieces in the city, this 100 floors tower was built in 1968 by the firm Skidmore, Owings and Merrill, becoming the second tallest in the world only after New York City back then. It offers the best views from the 94th floor. Admission is $26 for the day/night ticket, or $21 for a normal admission. Tickets here.

-Pumping Station and Water Tower The oldest structures in the city, and among the only ones that survived the 1871 Chicago Fire. It’s a block away from the Hancock Center in Michigan Avenue.

-860-880 Lake Shore Drive Apartments Designed by Mies van der Rohe. Two blocks behind the Hancock Tower, overlooking the lake.

-InterContinental Magnificent Mile Continuing south approaching the Chicago River. Built in 1929 at the height of the art-deco movement.

-Tribune Tower Designed by Howells & Hood in 1923, it is the most iconic neo-Gothic landmark skyscraper not only in Chicago but across the country. Pay attention on the lower levels at the rocks and pieces from landmark buildings across the world.

-The Wrigley Building Across Michigan Avenue from the Tribune, is the next iconic landmark, which together with the bridge across Chicago River and other buildings in the area, creates an outstanding showpiece of architecture. Built in 1924 modelled after the Seville’s Cathedral Giralda Tower combined with French Renaissance details.

-Michigan Avenue Bridge Across the Chicago River, it links Streeterville (northbank) with the Loop (southbank); the next important neighbourhood.

-River and lake boat tour 39$ adults, 35$ seniors for 1.5h if booking with Wendella Boats. These are very frequent, every 30 minutes or 1 hour depending on the time of day, and depart from under the Wrigley Building, where the ticket office is also located. First the boat will navigate along the Chicago River, then return back the same way and up to the locks, where the river meets the lake, and the last part of the trip is on the Lake Michigan, where the skyline view in unparalleled.

-Navy Pier On the east side of the district facing the lake. Original from 1916 however with many upgrades and restorations, it is the tourist attraction number 1 in Chicago. Full of amusements and arcades, and great views of the skyline.

  • Riverside Chicago hosts one of the most beautiful collection of buildings in the world and the riverside, the showroom of the most iconic, coupled with the largest collection of cantilevered bridges in the world. You will get to enjoy these all if you take a boat tour (highly recommended). Among them are:

-333 North Michigan and London House Chicago Hotel Both across the Michigan Avenue Bridge, creating a grand square. Art-deco and neo-classical at its purest.

-Mather Tower Just behind the London House Hotel. A masterpiece in the neo-Gothic style, with a fine narrow tower. The most slender skyscraper in the city.

-Carbide and Carbon Building A landmark Art Deco tower covered in black polished granite, dark green terracotta and gold leaf accents. Although located in the Loop, it is only behind the Mather Tower in Michigan Avenue.

-Trump Hotel and Tower The second tallest tower in the country.

330 North Wabash Behind the Trump Tower, is the landmark skyscraper by Mies Van der Rohe. Completed in 1973, 4 years after his death.

-Jeweler’s Building Across the river from the 330 North Wabash. Built in 1927 in neo-classical style was the second tallest outside of NYC.

-Marina City One of the top landmark buildings in the city, also referred as the “corncobs”. These twin towers became the new icon since the construction in 1967.

-United Building Opposite the corncobs, was completed in 1992 and designed by Spanish architect Ricardo Bofill.

-Reid-Murdoch Center Continuing west, easy to spot as the only rare building in red bricks. Dating from 1914 was to be used as offices and a grocery warehouse.

-Merchandise Mart After the previous building, this was once first on the list of largest buildings in the world. It sits near the junction of the North and South branches of the Chicago River.

-Civic Opera House Built in 1929, a condo tower of offices, apartments and the enormous Lyric Opera House of Chicago. Located along the south branch of the river.

-Two North Riverside Opposite the Opera, another impressive art-deco landmark that sits entirely underneath the rail tracks of the Union Station.

-Union Station A magnificent elegant beaux-arts structure with art-deco fittings. Opened in 1925

  • The Loop The core of the city itself. As a first touch to this area, you can make an entire loop by subway on the elevated trains, and then of course, all on foot as you will find some of the greatest sights the city has to offer.

-Michigan Avenue Likewise across Streeterville, it is the main thoroughfare  across this district. Here with some of the most exclusive residential towers facing the Millennium Park.

-Chicago Theatre In east Lake Street, just 2 blocks west from Michigan Avenue in the north side of the Loop, are that is called the Theatre District.

-Millennium Park One of the main urban parks in the city, with lots of public spaces and great taste for landscaping and architectural design.

-AON Centre Completed in 1973, was designed by Edward Durrell Stone and still stands as one of the highest skyscrapers in Chicago. Located at the north side of the park along East Randolph Street.

-Pritzker Pavilion At the north corner of the part, designed by Frank Gehry as a concert and exhibition hall.

-The Bean Or Cloud Gate, by the northwest of the park. This is tourist attraction number one in the area, where lots of people want to get their reflections.

-The Crown Fountain Where two LDC towers display faces of Chicagoan’s.

-Art Institute of Chicago The premium museum of art of the city, one of the largest in the country.

-Buckingham Memorial Fountain In the section of the Millennium Park already known as Grant Park, continuing south along Michigan Avenue. The skyline view from here is quite impressive.

-Field Museum of Natural History At the very south end of the Magnificent Mile (Michigan Avenue). One of the largest in the world in the subject. Nearest subway Roosevelt/Wabash (Green and Orange lines).

Adler Planetarium Not for getting inside unless you are fan of planetariums, but for the amazing skyline views you will get from here. Just east from the Natural History Museum.

-Harold Washington Library Located south of the Loop at 400 South State Street, the building was opened in 1991 as the largest public library building in the world. Worth to mention the winter-garden at the top floor, publicly accessible. The Loop subway has a stop right here.

-Federal Centre A block north from the Library. Famous square designed by Mies Van der Rohe, home to the 1974 big flamingo statue.

-Chicago Board of Trade Building West from the Federal Centre, best viewed from the South LaSalle Street. A 1930’s art-deco huge building, resembling the Rockefeller Centre of New York City.

-Willis Tower Formerly named Sears Tower, which in any case, it’s still the most commonly used name. You can go up the observation platform for great views over the city and beyond, but it’s more advisable to do this at the Hancock Tower. Its 2 blocks west from the Board of Trade.

-The Rookery In South LaSalle Street, a block north from the Board of Trade. A masterpiece by Frank Lloyd Wright, architect from the city, with its imposing hall and wrought iron stairs inside the lobby.

-Field Building Next door to the Rookery. Constructed in 1931 in the site of the original first skyscraper in the world, the Home Insurance Building from 1885. At one of the sides you can see the plaque with the historical description of this place.

-The Chicago Building In South State Street, it is the finest example of the Chicago School of Architecture, with its landmark windows too.

-Daley Plaza A block northwest from the Chicago Building. It is the principal civic centre of Chicago.

-Picasso Statue Donated by the artist in 1967, becoming immediately an unmissable landmark of the city.

-City Hall Completed in 1911 in beaux-arts. Along the western side of the square.

-Richard Daley Tower Completed in 1965 in international style, was the tallest structure in Chicago until the John Hancock Center was built.

  • Frank Lloyd Wright Tour As the city’s architect by excellence, and one of the most prominent ever, his works in the city are some of the finest, and for an architect lover it is a must to visit at least some:

-Frederick C. Robie House One of his landmark building. Located at the university, very near the 59th Station (University of Chicago) subway on the Orange line. A must!  5757 S Woodlawn Avenue.

-Isidore H. Heller House On the same avenue as the previous, on 5132 S Woodlawn Avenue.

-George Blossom House Quite near the previous at just 2 blocks north, 4858 S Kenwood Avenue. Nearest subway station here is 47th St. (Kenwood).

-Davenport House At 559 Ashland Ave, nearest subway Harlem/Lake on the Green Line, where many other houses by him are nearby.

-Walter Gerts House In 7214 Quick Ave, continuing the route from the previous house.

-Frank W. Thomas House East from the previous one 2 blocks, in 210 Forest Ave.

-The Hills-DeCaro House In 313 Forest Ave, few meters north from the previous.

-Arthur B. Heurtley House At 318 Forest Ave.

-Moore-Dugal Residence At 333 Forest Ave.

-Walter Gale House In 1031 Chicago Avenue.

-Wright Home and Studio This was his personal house, the next building after the Walter Gale in 951 Chicago Avenue. Impressive like no other, nowadays a museum about his life and works.

-Ernest Hemingway Boyhood Home Not designed by Wright, but it’s in the same neighbourhood next door to the other buildings. Located at 600 N Kenilworth Ave.

-Harrison Young House By 334 N Kenilworth Ave.

-Ernest Hemingway Birthplace Also, not designed by Wright, but in the next street after the Harrison Young House, in 339 N Oak Park Ave. From here you are near Oak Park subway station you can use to return to the city.


The main and major port of arrival or departure in the city is its huge O’Hare International Airport, and secondly, the smaller Midway Airport. Flight to/from anywhere in the world are likely to have a route serving the city. From O’Hare here is the Blue subway line running towards the Loop every 15 minutes, 24 hours through the 7 days of the week. Along the way, other subway lines are intersected, therefore covering you to anywhere you need to go in a rather fast, very convenient and cheap way. Midway Airport is much nearer to the city centre, hence the time commuting is halved via the Orange Subway line.

Please note that if boarding the subway at O’Hare, an extra 5 USD is added to the 2.25 single ticket. However, if boarding in the next station after O’Hare, then it’s the normal fare across the entire network of 2.25 per ride. The way of getting a ticket is acquiring the Ventra Card (magnetic card the stores value as electronic wallet). The card costs itself 5 USD, refundable as fare to use when registering the card online, and you add money on the go as you need to. Visitor passes are sold for unlimited travel on the CTA on 1 Day (24 hours) for $5.75 or 3 days for $14. Other passes for longer validity are available too. Check at the station what is best depending on how many days you will be staying. These passes are valid on all subway lines and buses.

Coming overland is the next great option. Chicago is the main railway centre of the USA, historically and actually still being the case. Major cross-country railway lines meet at Chicago, with almost a direct link with any capital city of any state. Commuter railways  (METRA) serve the entire region and towards the nearby surrounding states.

Within the city, Chicago has the second largest subway system in the United States, and second largest urban and inter-urban buses after New York City. Going anywhere in the city is simple and fast, but also inexpensive in such a great public transport system.

As last and as mentioned before, this is one of the best walkable cities in the United States. It is the most pleasant way for visiting most of its sights, especially these within the Loop.


Chicago, the city with one of the largest choice of accommodation of any kind, yet one of the most expensive per night. Finding a deal is quite rare to be honest, and no matter which season of the year it is. The second most visited city in the country, either by tourists or by business people on and on. You have a massive selection from some of the finest hotels in the world, top luxurious, to the more modest, and a vast array of B&B, airb&b, hostels and rental apartments. Name it and you have it. The usual note in here, a good and reasonable point to start your search is by checking some of our preferred affiliate hotel search engine such as,, Expedia,, Agoda, Opodo, LateRooms or Ebookers.

While I cannot suggest any longer the hotel we stayed back in the 2012 trip as it closed down, I can for sure highly recommend the one we stayed in this occasion. However, bear in mind it is not in the city centre nor near the loop, but next to O’Hare airport. It was very unfortunate going this “far” (just 35 mins in the Blue Subway line to the Loop anyway so not bad); but the fares were shockingly high in September, and any high summer season months. We stayed at the SpringHill Suites Chicago O’Hare by Marriott, in 8101 West Higgins Road. This is few minutes walk from Cumberland Subway station of the Blue line, meaning you do not have to pay the extra 5 USD for riding the subway at O’Hare, since you are already 2 stops nearer to the city. Very conveniently connected to the city 24 hours a day in little over 30 minutes to anywhere in the Loop. The property was fantastic in every sense, from the friendly and welcoming staff, to the care and cleanliness of the building, the spacious quiet and comfortable rooms, and the nice breakfast each morning.

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