I usually write about my Top 5 favorites in places that I go to, and I’ve always wanted to write about my fun-filled two weeks in Chicago when I kicked off blogging. The reason I’ve procrastinated is because I struggle to choose just 5 favorites about The Windy City.
To give a bit of a background: the first time I got see Chicago was 13 years ago, when I went to Illinois for a short business trip. Back then, I squeezed in what I could for only about 3 days, on weekends. Despite the short trip, I was already mesmerized by the vibrant city. It was also my first visit to the United States, and at the time it was autumn. Coming from a tropical country with only 2 seasons (dry and wet) and mostly hot and humid all year round, I quickly fell in love with autumn – the cool temperature, and the beautiful colors of the changing leaves. Subsequently, almost all holidays I had with D fell around the autumn months.
Except for the second time I went to Chicago, this time a sort of longer trip. It was winter of 2008 and we spent time with relatives. Winter is an interesting season for D and me – but we decided we’d stick to our autumn holidays.
So this year, first time after 10 years, I visited Chicago once again. It was almost summer when I went, so I had a share of the changing temperatures from cool to warm. I went to Chicago after my solo travel to Montreal. I stayed with my aunts for two weeks and was able to spend more time with relatives during this trip. I’m very thankful to my aunts Jane, Salud, Bel and Zeny; uncle Oscar; cousins May, Juvy and Mike: they warmly welcomed me to their homes, showed me the beauty of their city and allowed me to get to know Chicago more up close and personal.
Chicago’s Art Scene
I first visited the Art Institute of Chicago when my cousin Juvy and I did the Big Bus Hop-On and Hop-off tour. Prior to going, I read that this museum was rated one of the best museums by TripAdvisor for some years now so it definitely was a must to visit. The grand entrance was beautiful, with its lion statues. There were friendly staff and maps located everywhere in the museum which really helped as the museum was big and one could easily get lost. My favorite exhibits were the Impressionist, New Contemporary, Medieval and Renaissance art galleries. We only spent a couple of hours in the museum and I would love to go back. I think I’d need at least a full day to explore the Art Institute of Chicago. My favorites works of art were The Old Guitarist by Pablo Picasso, and the portrait of Elizabeth Taylor by Andy Warhol.
I went to the Museum of Contemporary Art (MCA) which my niece recommended. She said I wouldn’t miss the steps to the entrance of the building. She was right – and I just had to take a photo. I got to visit the MCA during their free museum day. I find contemporary art interesting and this was a good place to start exploring.
The next museum where I had free entrance to was the Loyola University Museum of Art (LUMA). I had to do a bit of research before finding this museum and including it in my To Go To – I understand it was not as well known as the first 2 museums I went to. It’s in the Loyola University at N Michigan Ave, near the Old Water Tower. This is my second favorite museum, next to the Art Institute of Chicago. Their gallery was small, but I really liked their exhibits. At the time, there was an exhibit by Gregory Beals called They Arrived Last Night; and a photography exhibit by Tonika Lewis Johnson called Everyday Englewood. I was looking at the photos by Gregory Beals and there were moments I teared up. The photos were very captivating, and they incited a lot of emotions from me as a viewer. The permanent displays at the third floor had a lot of religious relics. Photos were not allowed inside the museum.
Another way that I appreciated art in Chicago was whenever I stumbled upon street art. Here are some of the delightful street art finds while walking the streets near Wicker Park:
Walking in the parks
Top of mind when it comes to Chicago parks is the Millennium Park. Been here four times (I went twice during this last visit, bringing my friend Paolo with me) – and I never get tired of it. It’s a nice place to stroll, or take in the surrounding buildings’ architecture. In every visit, I watch the water being squirted by the different faces displayed at the Crowd Fountain; and take selfies at the Cloud Gate (also known as The Bean).
Walking distance to the Millennium Park is the Grant Park where Paolo and I gazed at the Buckingham Fountain.
The Lincoln Park is somewhere I had to commute to from my aunts’ place at Wicker Park. I took the bus with a ventra card to get there and it was worth the trip. The park was big, and I did have a good long lovely walk. I got to the Lincoln Zoo – I try to avoid zoos as much as I can but this was the last stop of the walk along Lincoln Park. In this zoo, I saw the lions sleeping and I wondered if they could really have a peaceful sleep as the kids around me were shouting at them – this was the part that broke my heart.
Wicker Park was walking distance from my aunts’. It’s a small park close to a lot of good restaurants (like Stan’s Donuts where I got my bagels from; Goddess and Grocer where I got a healthy salad snack; and cafes). I’ve been curious about this because I remember a movie starring Josh Hartnett entitled Wicker Park. I liked that movie.
A few minutes’ walk from the wicker park is the 606 trail. It is an elevated trail for bikers and runners and I also saw an art sculpture along the way. 
Last on my list is – and I’m not sure if this falls under the parks category – the Garfield Observatory. It showcased different plants and flowers – I was quite overwhelmed by the pretty blooms from different seasons!
Diverse Architecture and the Chicago Skyline
A good way to see the most of Chicago’s architecture is through the hop on and hop off bus tour, and the Chicago Architectural River Cruise. The river cruise gives a good vantage point and the guides gave detailed information about the buildings’ histories. One of my favorites is the historic Old Water Tower.
For the Chicago skyline views, the best place in my opinion is to view it from the museum campus, next to the Adler Planetarium. I go here every single time I am in Chicago and like the Millennium Park, it never gets old. Other places for the skyline view are the Navy Pier and Lincoln Park.
Paolo and I also did the Riverwalk. We stopped several times to appreciate the buildings along the river, and also to enjoy the sunset next to the City Winery. I also met a cute dog being walked along the City Winery – he’s sooo adorable!
U2 Concert!
This was a super awesome surprise welcome gift to me by Mike and Juvy – I was ecstatic!! I’ve always wanted to watch a U2 concert so I was pumped when Juvy showed me the tickets. I literally cried tears of joy. We watched it at the United Center. The concert’s production was high tech and spectacular. Left me humming to Beautiful Day every morning during the rest of my trip. I’m actually listening to a U2 playlist in Spotify as I am typing this blog now.
Chicago Cubs
First baseball game I’ve ever watched live. I remember how I used to like playing baseball in high school. It was fun (and surreal) going to the Cubs vs Giants game – there were stores selling shirts, caps and other items around the area; beer and hot dogs were overflowing; and the fans were dressed up to their teams. Some of the fans were seated on the rooftops of the nearby buildings – hats off to them because it was so hot that day yet there they all throughout . There’s a park outside with a huge screen playing the game.
Two weeks isn’t enough as there are just too many things to do and explore in Chicago. Still, I am grateful for having been given the opportunity to visit this city once again and spend time with relatives and friends. Next time I would love to watch some theater plays or shows and spend more time in the museums (visit more of them too).
I’m sure next time I go to Chicago, I’d come across more spectacular finds (just like the giant pretzel from a bar I went to with my cousin – I was just speechless in awe!)
Living Free and Making a Difference 
Nice review! Looking forward to reading more…
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Hi TJ nice to bump into you here in WP!
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This is such a fabulous trip! It looked like so much fun!😀
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It was! I was blessed to have warm welcoming relatives there
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You squeezed so much into this trip, looks like you had a great time! I always loved the art scene in Chicago, so many spectacular small theaters as well.
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