USA Series · USA Travel · Weekend Guides

A Weekend In: Chicago, Illinois

Spending a year in Indianapolis, less than a three hour drive from ‘America’s 3rd city’, there was no way I was going to pass by an opportunity to visit Chicago! It actually took me almost the entire year to find a suitable weekend but it worked out really well in the end as I went up to Chicago with the Student Latino Organization and this gave me the opportunity to see a part of Chicago that I never would have on my own.


Seeing as I was actually on a tour with the Latino society the first place we visited in Chicago was the Pilsen Neighbourhood, one of the fastest growing areas of ‘Mexican America’ in the USA. Pilsen is home to the National Museum of Mexican Art as well as countless  Mexican restaurants, bakeries, convenience stores and several beautiful murals depicting Mexican-American life.

IMG_3036National Museum of Mexican Art

Perhaps a bit off the beaten path of regular Chicago tourist attractions, I would definitely recommend this museum as somewhere to experience a different side of the city. We went on a pre-arranged group tour and so we had a tour guide to explain the important exhibits to us, but there are plenty of info leaflets that will give you more or less the same information (having said this, get the tour if you can!). Entry is free with optional donation but you’ll probably find its worth donating a few dollars at the end.

Mexican BakeriesIMG_3047

You absolutely cannot leave Pilsen without visiting, and stocking up at, a Mexican bakery. There are plenty to choose from and I’d recommend 100x over Mexican chocolate chip cookies. These cookies are huge and have the chocolate chips put in after baking so they sit melted on the top, incredible!

Downtown Chicago

Driving from Pilsen to downtown one of the things I said was “It looks a lot like Indianapolis!” The girl next to me on the bus was from Chicago and she looked at me like I’d just said something really stupid. Sure enough, as we got closer and closer the city got bigger and bigger and then even bigger and I realised that the only way Chicago could look like Indianapolis would be if Indianapolis’ buildings grew to three times their size, Chicago is BIG!

IMG_3068Millennium Park

When it comes to downtown Chicago one of the classic places to visit is Millenium park. This park is right in the centre of Chicago and is where you can visit ‘the bean’ and take a million reflective pictures. Millenium Park also has concert venues and sculptures and a beautiful water-wall with projected images on it. It’s a great place to wander around (but remember to wrap up, the wind in the Windy City is just as cold as you’d think!)

Art Institute of Chicago

The Art Institute is on the same street as the entrance to Millenium Park and so it’s very easy to find. As you’d expect with a large art museum the building is impressive and worth going to see even if you don’t go inside. There is a an ever-changing main exhibit, which was actually on Ireland when I was in  Chicago but unfortunately I completely ran out of time to see it. Entrance to the Art Institute is $25 for out of state residents so it’s worth setting aside a fairly large chunk of time to make your money worth it.

Willis Tower/Sears TowerIMG_3105

The name of this tower is often contested by Chicago residents. The Sears Tower was completed in 1973 and became the tallest building in the world until the Malaysian Petronas Towers were opened in 1998. In 2009, due to a shift in the building’s use the tower was renamed ‘Willis Tower’ but Chicago residents maintain the use of its original name.

This building and its famous ‘Sky Deck’ is probably Chicago’s biggest tourist attraction. Due to my tour of Pilsen in the morning I didn’t get to the tower until 3pm and it took me over two and a half hours to get to the sky deck because of the queues! So a definite recommendation is to go early and try to avoid going on a Saturday. Entrance is $20 and although the queues are long and many there is an effort made to entertain people stood in these queues with interactive quizzes and history of the building printed and projected onto the walls. The final elevator ride up to the Sky Deck is an experience in itself as the ceiling of the lift advises you how many of the world’s landmarks you are now higher than (basically the Eiffel Tower is tiny…)

Once you get to the sky deck the stress of the queues will disappear as you take in the absolutely incredible views from the 103rd floor. There are several glass viewing platforms sticking right out over the Chicago street which are what the Sky Deck really sells itself on. For an extra price you can have your photo taken in a special one of these glass boxes, or you can ask a kind stranger to take a photo of you for free in a different box with a slightly less cool, but still amazing, view.


You can’t go to  Chicago without experiencing real Chicago deep dish pizza and it’s available on pretty much every street corner. Another Chicago Classic is Garret’s Popcorn. Get the ‘Chicago Mix’ which is caramel and cheese flavour, it sounds horrible but I promise it’s amazing!

I only spent a single day in Chicago and I experienced so much! It’s definitely on my list to return to some day, there is so much to see and do in this city and it’s a beautiful place!

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