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Windy City Wonders: A Weekend Itinerary for Exploring Chicago


Chicago skyline
Chicago skyline

Welcome to the Windy City! If you're looking for an exciting weekend getaway, Chicago should be at the top of your list. From its iconic skyline to its world-renowned cuisine and vibrant cultural scene, Chicago offers a plethora of experiences for every type of traveler.


In this post, I'll guide you through the must-see attractions, the hidden gems, and the best places to eat, ensuring that your weekend in Chicago is nothing short of spectacular. So, buckle up and get ready to immerse yourself in the sights, sounds, and flavors of this magnificent city. Let's dive into our ultimate weekend guide to Chicago!


Chicago is the third largest city in the United States, also known as the windy city, is the city where the mythical Route 66 begins, and is known for its "Deep Dish" pizzas.


What to see and do in Chicago in 3 days


Visit the city by cruise ship


It can be said that the heart of Chicago is the river that bears the same name (Chicago River) and runs through the center of the city. Around it we will find a pedestrian promenade called Riverwalk.


We did the tour with Wendella Tours & Cruises. What does this tour have to offer? Because architecture is one of the strengths of the city, this tour offers a river tour aboard its cruises where you can appreciate most of the iconic buildings of the city, while a guide explains their origin, to which architectural current they belong, as well as the relevance they have within the city.


Chicago by boat
Chicago by boat

Chicago by boat
Chicago by boat

Millenium Park & the most famous bean in the world


It may be one of the most famous and photographed places in Chicago. The Cloud Gate better known as The Bean for its shape, is composed of 168 steel plates weighing 98 tons.


The Cloud Gate, Chicago
The Cloud Gate, Chicago

A few meters from the Cloud Gate we will find the interactive Crown Fountain, designed by the Catalan artist Jaume Piensa, an installation that consists of a small space in Millennium Park where two towers are located, one in front of the other. These towers are actually screens composed of LEDs that reflect different human faces in turn; each face changes expression until a moment comes when water begins to flow from the fountain and it seems that it comes out of the mouth of the face reflected on the screen.


Crown Fountain, Chicago
Crown Fountain, Chicago

Navy Pier


Navy Pier has had different uses throughout its history: it was once one of the largest piers in the world; then, in World War II, the pier was ceded by the City of Chicago as a training area for the U.S. Navy. Today it is a center of attractions where tourists and locals alike can find plenty of options to spend their time.


Navy Pier, Chicago
Navy Pier, Chicago

Navy Pier, Chicago
Navy Pier, Chicago


Navy Pier, Chicago
Navy Pier, Chicago

Go to Skydeck Willis Tower and take a picture on the glass floor


What was once called the Sears Tower, and today bears the name of Willis Tower, has on the 103rd floor one of the most precious jewels for the city of Chicago. It is the Skydeck Chicago viewpoint, which has a privileged view of the city and four exits with glass coverings and floors through which you can peek, step and even jump on them: "The famous glass floor, which was adapted because many visitors were curious, not only to look into the distance, but to see how it looks down.


SkyDeck Willis Tower, Chicago
SkyDeck Willis Tower, Chicago

The cost for adults is $23, while the VIP pass costs $49, which you may want to consider purchasing because when there are a lot of people, the line to get in can take up to two hours.


The views were very nice, but I wouldn't come back again to this building. To go to the glass flour area you'll need to wait a long time and once you get there, you'll only have 2 minutes to enjoy.


The Chicago Theatre


An institution in the city, don't tell me that red sign with white letters doesn't ring a bell! It has been offering performances since 1921 when it was the most expensive and largest theater in the country. The greatest artists of the time have performed here and it has been the venue for important film festivals. Nowadays you can visit it in one of its events or with a tour.


The Chicago Theatre
The Chicago Theatre

The Field Museum


It is the museum of natural history, one of the most important in the world in its field. Apparently it has such a large collection that only 4% of all objects are shown. Although its right eye is undoubtedly Sue, the largest, most complete and best preserved T-Rex skeleton in the world (beware, the head that accompanies the rest of the body is a replica, for reasons of weight the original is exhibited separately).


The collection of fossils is also impressive (in fact you can see the team of paleontologists working through some glass, and yes, they are real). In the rest of the rooms of this immense museum there are exhibitions that make a journey through the history of the planet, in different periods and cultures.


The Field Museum, Chicago
The Field Museum, Chicago

Search for sculptures in the city


As we have seen, Chicago is a city that promotes art and culture and for all its neighbors and visitors to enjoy it, several sculptures have been placed around its streets. There is a particular area where three of the most important ones are concentrated:


  1. The Picasso: some say it is a dog, others say it is a fox... even a bird! We'll keep that it's a Picasso, you don't always have to look for the answer to everything!

  2. Miro's Statue, another work of a Spanish artist to which we don't have to look for a lot of explanation.

  3. Calder's Flamingo, this one was given a definition, although it is as much of a Flamingo as I am of a tooth fairy.


The Picasso Sculpture, Chicago
The Picasso Sculpture, Chicago

Transport yourself to Gotham City


For Batman geeks, this little corner of Chicago probably rings a bell: it's LaSalle Street and Jackson Blvd and it's where some of the Gotham City scenes are set.



Chicago Riverwalk


Chicago is one of the most "walkable" cities in the United States, to reinforce this theory is the Riverwalk, a pedestrian walkway that runs along part of the banks of the Chicago River, no more and no less than in downtown itself. Although it is difficult to forget that you are in a big city (the skyscrapers will never disappear), it is quite pleasant to take a walk here, there are also many seating areas, restaurants and cafes.


Look at the twin buildings of the Marina Towers, and especially on the second floors: they are the ones that are intended for parking and you will only see the back of the cars, apparently they have professional valet parking to nail the car in place, so that no clumsy person is left with the accelerator pedal to the metal and flies away.



Chicago Water Tower y Pumping Station


The only buildings that remained standing after the great fire in Downtown Chicago were these two, and they have become the symbol of the old city and the spirit of recovery. They are two strange stone buildings that look down their stretched necks at their imposing new neighbors of steel and glass, but were once the real deal breakers.


They date from the 1860s and served as a reservoir and water pump to distribute water to the city. Today they house free art exhibitions.


Chicago Water Tower
Chicago Water Tower

Chicago Cultural Center


Where you can see a striking glass dome. But beware, it is not the only one! Get a little lost in the building to find another much less known room with another huge dome, almost as impressive as the main one. There are also some free exhibitions to visit (and baths!).


Chicago Cultural Center
Chicago Cultural Center

Eat the typical Chicago pizza


You may not know that one of the best things to see and do in Chicago is: eat! Specifically, Chicago-style pizza, the city's signature dish. This strange pizza looks more like an empanada or a meat pie, but it's delicious anyway.


Keep in mind that they are real bombs, you'll probably order one and eat half, so you know, don't leave what's left over and take it for dinner, you never know. Two good places to try it are Giordano's and Pizzeria Uno.




Bar & restaurant recommendation


Bar recommendation Offshore Rooftop - 1000 E Grand Ave, Chicago, IL 60611, United States - NAVY PIER AREA


Restaurant recommendations

Gordon Ramsay Burger - 2 E Ontario St, Chicago, IL 60611

Giordano's - 223 W Jackson Blvd, Chicago, IL 60606


USEFUL INFORMATION


How to get around?

  • Walking: If you are staying downtown, the distances seen on the map are deceptive, everything is closer than it seems and you can really move around Chicago on foot without any problems.

  • By subway: No doubt to use the subway it is worth it to use a pass. Only one ticket costs 2,50 dollars, the one day pass costs 5 dollars and the 3 day pass costs 20 dollars. If you are not going to use the subway, it is worth buying a ticket for your stay. A practical fact here: you should know that the metro vouchers (1 or 3 days) expire after 24 hours, they do not work for calendar days. In other words, if you take it out at 15:50, it will expire at 15:50 as well.

  • Car: Totally inadvisable because of the price of the parking, super expensive. Better forget about the car, especially considering how easy it is to get around on your own without having to use it.


Where to sleep?

We stayed in the Magnificent Mile district and the area was safe and we were in the middle of the city center. We went everywhere walking. If we had to recommend an area to stay in Chicago, it would definitely be along the Magnificent Mile. Also known as N. Michigan Avenue, it is the commercial artery of the city. To put it in a nutshell, it is to Chicago what 5th Avenue is to New York.


The hotel were we stayed was: The Chicago Hotel Collection Magnificent Mile Hotel & Suites


However below you can see other nice areas where to stay:

- River North: It is a commercial district with a great nightlife. In this neighborhood there is the largest concentration of art galleries in the United States, second only to Manhattan. In recent decades it has evolved a lot and have been built large buildings, nightclubs and many restaurants that have given another roll and have made it a good area.

- Streeterville: And on the other side of the avenue, closer to Lake Michigan, is the Streeterville district. It also has many hotels, although we think it has quite a different vibe than the River North District. Although it is home to some restaurants, we think it is a rather duller part. It is a quieter area to stay in Chicago, with universities, hospitals... but also very safe.

- Theater District: North of the Loop, as Downtown Chicago is known, is the Theater District. It is a commercial and entertainment area .It is a pretty good area. There are many hotels and it is very close to everything. You are only a 5 minute walk from Millennium Park and the Magnificent Mile.

- Chicago Loop: It is the Downtown of the city, its financial area, where the big businesses of one of the most important cities in the United States move. Apart from the headquarters of very important companies, there are also several museums, universities and interesting parks such as Grant Park.


We don't like to sleep in the downtowns of big cities because at night the atmosphere changes completely. When people go home after work, the area gets a bit lonely and can give a feeling of insecurity. Even so, we think it is a good area to stay in Chicago because there are many good hotels in the area.



These are our recommendations of the best things to see and do in Chicago, we enjoyed it very much. Do you know more things to visit in this city of Illinois? Leave us your recommendations in a comment!

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About me

Hi there, Welcome to all about 'meryca! I'm a Spanish girl living abroad who loves to travel and to discover new restaurants. I'm constantly searching for the best places to eat and drink. ​

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