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What to do in Chicago? Complete Travel Guide

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Traveling to a new place can be daunting, let alone a city that has a lot to offer. How do you try to find out what attractions to see, where to go and which ones are worth jumping? This is especially important when you are going on a short trip and want to maximize your time. Wasting time going to an attraction that is not worthwhile or worth waiting for is a point of frustration for me.

My goal today is to provide a Chicago itinerary on what attractions to visit on a trip of two or three days (or more). Each traveler will have different tastes / interests and likes / dislikes, so not all of these recommendations will be suitable for everyone. Also, Chicago is a huge city and there is no way that all attractions, restaurants or events can be handled in this publication. This itinerary will mainly focus on the main attractions that we recommend visiting while and what to do in Chicago. In the future, we will visit this great city to fill the gaps, providing more information and comments on attractions, events, restaurants, etc.

Chicago Top Attractions Travel Guide

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Whether you are a relaxed traveler or an active tourist, you have small children, teenagers or not, we all travel differently. Even in several stages of our own life, we can have moments when we are not as quick as before. In the past, you may have seen six attractions in one day, now you are lucky to see four. The point is that you know what will best serve you to make this or any trip the most memorable and enjoyable. We are here to help and give some recommendations of what we have found during our time in Chicago. Even if you stay longer in Chicago, use this itinerary as a guide to know what to expect.


Do not you dare to sleep because we have a lot to do! The first day will be about something of culture, history and science. Depending on your pace and how much you want to see, you can try to do everything OR, choose two or three that really interest you and spend a little more time on each one.

Willis Tower (in particular, the Skydeck): the tower formerly known as Sears Tower, the classic Chicago building that is found in almost every image of the Chicago skyline. The building is 1,353 feet high and has several glass observation shelves that allow you to stand in this glass box and look down. On a clear day, you can see approximately four states from the observation platform. Also, there is a restaurant on the 99th floor available if you’re hungry or if you want to eat with a view. The Skydeck is open from 9 am to 10 pm (April to September) and from 10 am to 8 pm (October to March). The longest part of this attraction is simply to climb the Skydeck. If you have your City pass or Fast Pass, it will go much faster than having to queue and buy tickets. There will be a small line to climb, but the tower does a good job of raising and lowering people. Once you’re up, it does not take long to see everything, it just depends on how much time you want to spend. Going back down can also take a while. Plan 45 minutes to an hour.

1 Chicago Art Institute

Chicago Art Institute

Recently voted the number 1 museum in the nation, it goes without saying that this is one of the best art you will ever find. The walls are adorned with some of the most iconic artists and some of their best works.

His selection of European painting has some of the best works in the world, including the main Impressionist, post-impressionist and modern works that are incredible. For those who like to study each painting and read each description, book at least three hours. For those who only go to see the main works, it could probably be done in an hour to an hour and a half, maybe a little less. The museum opens every day at 10:30 AM and is open until 5:00 PM. If you’re hungry, the museum offers a couple of options, but be careful because they’re expensive.

Chicago Art Institute Travel Guide

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2 Millennium Park

Millennium Park

Millennium Park is home to the famous Cloud Gate, also known as “The Bean”. One of the largest attractions in the city, Cloud Gate offers a truly amazing work of art with the city skyline as a backdrop. While you’re there, you can be a child and jump into the water between the Crown Fountain that reflects the faces of Chicago in a 50-foot tower. During the winter, an ice rink is offered to try skating. While there, sit down at the Great Lawn or enjoy a show at the Pritzker Pavilion.

Millennium Park Travel Guide

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3 Grant Park

Grant Park

with the lake in sight and the Art Institute still nearby, wander through Grant Park to see the Buckingham Fountain. The beautiful fountain shows a wonderful display of water that shoots the water 150 feet into the air. The initial screen is at 9:00 AM and every hour in the hour in operation for about 20 minutes. On the southwestern side of the park there is an amazing work of art called Agora, which has more than a hundred nine-foot-tall headless torsos made of cast iron.

After taking the fountain, our next stop is the Museum campus, which houses the Field Museum, the Adler Planetarium and the Shedd Aquarium. This is where you will perhaps feel essential to make a conclusion It is possible to do various things, but I would have to be extremely lucky with the lines and zoom in all the exhibits. You will probably not be so lucky and, therefore, it will be necessary to make a decision. To get here, you can take a nice walk, about 2 km from the Art Institute or take an orange or blue line with a short walk to get to the museums.

Grant Park Travel Guide

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After an extensive day, you have so numerous choices. You can take some food or even return to the Art Institute or I would suggest going to the 360 ​​Chicago Building (formerly the Hancock Observatory) located three miles to the north. To get there, you can walk (3 miles north), take a taxi or take a combination of public transportation options, including the blue and red lines. The journey can last between 30 and 40 minutes, but it will be a pleasant relief for your feet. If you press for time, choose the taxi.

4 360 Chicago

360 Chicago

Another skyscraper that offers some of the best views of the city. A new attraction called TILT is now offered that offers visitors a downward view from 1,000 feet up. The line is extended but the observatory is open from 9:00 a.m. at 11:00 p.m. with the last entry at 10:30 p.m. The observatory was voted one of the best points of view in America by Travel and Leisure. There are some interactive activities for children if they are interested.

360 Chicago Travel Guide

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Day 2: A little Architecture and Shopping.

5 Architecture Cruise

Architecture Cruise

This is undoubtedly one of the best activities we have done. The tour is very informative but also very entertaining, you can see and learn a lot about the city, as well as get unique views of the different buildings, including a trip to the lake to see a tremendous view of the entire skyline of the city. Our individual endorsement is the First Lady Certified Chicago Architecture Foundation. The course is given by the teachers of the foundation of the real architecture who have studied and really know their material. The tour lasts about an hour and a half, but you must show up 30 minutes early to make sure you get a good seat. Depending on the time of year, you may have to bring a light jacket.
Tribune Tower / Wrigley Building- Across the river: is the historic Tribune Tower and the Wrigley Building. You do not necessarily have to go inside the buildings, but both are excellent buildings to take some pictures.

Architecture Cruise Boat Tour

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6 Marina City (also known as the corn cob towers)

Marina City (also known as the corn cob towers)

walk a little west to a couple of blocks to see this landmark building. This is the same as the previous one, it is worth taking pictures, but as it is a mixed use residential / commercial building, it is not worth entering. The corn cob towers are the famous towers that were shown in Steve McQueen’s movie, “The Hunter,” and appear in the background in several popular movies such as The Blues Brothers and Ferris Bueller’s Day Off. You will have many pictures of this building from the architecture cruise, so if you do not have time, you can skip this.

Marina City – Tour Tips

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7 Navy Pier

Navy Pier

home of the great Ferris wheel and different entertainment options, Navy Pier offers several attractions to fill your time. For me, Navy Pier is fine, but it is more oriented towards the tourist and the younger population. The Chicago Children’s Museum is there, as well as a stained glass exhibit, but this area is primarily for children. Various boat rides and cruises are offered that appeal to all ages, including the “cruise” Seadog, which is a speedboat, or the Tall Ship Windy, which also features the occasional pirate cruise, among the many boat offers.
During the night, check the area and local events to see a concert at a local blues bar or a musical that is in the city.
If you have three days, here is an additional one day itinerary.

Chicago – Navy Pier Travel Guide

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Day 3

8 Lincoln Park Zoo

Lincoln Park Zoo

a truly incredible find. This is a excessive zoo with numerous animals to see. Best of all, it’s free! Right next door there is a greenhouse that is also fantastic and worth a look. If you decide to drive, you will have to pay a parking lot that will cost between $ 20 and $ 35. Communal conveyance is also a good choice and will save you some money.

Lincoln Park Zoo Tour

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9 Wrigley Field

Wrigley Field

If you can do this before day 3 because you have tickets to a game, do it. If it’s not the baseball season or the Cubs do not play at home, check out the tour at the legendary Wrigley Field. Whether you are a baseball fan or not, this is a must for any visit to Chicago. A tour will last between 75 and 90 minutes and there are several options available depending on how much you are willing to pay. Be sure to check the website to get your tickets before they run out. Day trips that are not games allow you to visit the clubhouses and the dugout, which is always an advantage. I always recommend trying to see a game if you can, as it will give you a great sense of history.

Chicago Travel Guide: Thing’s To-Do at Wrigley Field

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10 Sign of Chicago

Sign of Chicago

located in the Chicago Theater, this is another of those places that you have to take a picture of. If you are able to see a show here, do it by all means.

11 Museum of Science and Industry

Museum of Science and Industry

The building was part of the World Fair in 1893. Be sure to visit its website to obtain additional entries necessary for certain exhibitions. A submarine U505 is one of the special attractions that is worth seeing if you are in the area.

Museum of Science and Industry Chicago Tour

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12 Chicago Blackhawks

Chicago Blackhawks

if you can attend a Blackhawks game, you must do it. The atmosphere is different from any other you will find in professional sports. The crowd is singing, cheering, singing and completely in the game. It has a special feeling and, even if it’s hockey, this is a wonderful experience that you will not regret. You could even become a fan of the Blackhawks.

There are also many other options, not to mention everything that needs to be done in the suburbs. Hope you would got what to do in Chicago and loved our amazing Chicago travel guides.

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