A long weekend in Chicago

Seems like everyone is going to Chicago these days. It’s a popular place to visit for good reason. Chill vibes, cool art, good food. It’s all there!

Ah Chicago! I wish I had more time to see more of you! If you’ve been thinking about heading to the Windy City, there’s no better time than now. Here’s how I spent a long weekend in Chicago!

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What a wonderful weekend

I started out the weekend playing at an ultimate tournament. (More about ultimate the sport here.) The weather was mostly good and we had a great time!

Although we didn’t do a whole lot of exploring together, we did get deep dish pizza in the middle of a huge thunderstorm. The food was amazing! I had a great gluten free pizza base, so unfortunately am still a deep dish virgin. This restaurant was great about accommodating our large group, though, and had plenty of options for everyone’s tastes.

What to see and things to do in Chicago

The lake and the pier

Walking along the lake is a pleasant way to see different parts of the city and enjoy the views of the water. The pier is an iconic part of the city, with incredible views back on the cityscape.

If you aren’t going to the pier to do any of the activities there, I would recommend going early in the morning. I got there just before 9AM on a weekday, and I was one of the first travelers walking around the pier.

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The fountain

I wasn’t sure whether I should check out this fountain, but I’m glad that I did! It reminded me of fountains that I’ve seen in Europe. This is the Buckingham Fountain.

I went earlier in the day as well for this and it wasn’t very crowded. You can get some great selfies here with the city in the background!

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Chicago Cultural Center

This is a historic building in central Chicago with free exhibits to check out and a seating area with free WiFi. The building itself is impressive and fun to explore.

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My favorite exhibit when I went was “The Wall of Respect: Vestiges, Shards and the Legacy of Black Power.” It’s an interesting piece of Chicago history that I would never have known about had I not walked into this building!

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Museum of Contemporary Art, The Murakami Exhibition

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Wow. Just wow. The Murakami exhibit was my favorite part of the weekend.

This is the first time in my life where I’ve ever felt that I could see myself buying a piece of art. Or more realistically, a print, because let’s be honest originals are super expensive). Even the prints were coming in in the thousands of dollars.

But if there is one museum or exhibit you go see in Chicago, it should be this one. I liked the story of the exhibit, and his career really, of becoming popular and working with big companies but then taking a step back and going back to his roots. I’ve never quite understood high art or high fashion, and his transition to more thoughtful and spiritual works speaks to me.

I don’t think I could ever justify spending so much money until I start earning loads, but I did buy myself a few postcards of my favorite pieces shown at the exhibition.

Here are a few photos of my favorite parts of the exhibit. While this exhibition is now over, I wouldn’t hesitate to head back to the Museum of Contemporary Art Chicago!

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The 606 trail

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On the 606

The 606 trail is an elevated bike and pedestrian path that goes East-West in the northwestern part of Chicago. It was an abandoned rail line, similar to the High Line in New York City. But unlike the High Line, it’s purpose is to serve as an alternative transportation corridor as well as green space. It goes through a few trendy neighborhoods and goes past the large park.

I walked the entire length of the trail, and it took about an hour and a half. There will be a lot of cyclists on the trail, but also people on foot and moms with strollers. If you have a few hours to spare and want to have some time above the streets, this is awesome for that.

Where and what to eat in Chicago

The Chicago Diner is one of the oldest vegetarian restaurants. You can even buy some diner swag in the restaurant if you are a fan. I had the avocado tostadas and sweet potato fries. Nothing fancy, but great food!

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My first time eating a poke bowl!

Hawaiian style Poke bowls (not to be confused with Pokemon balls) seem to be trendy in all parts of the country now. These are essentially a Hawaiian style salad bowl usually with some raw seafood on top. There’s a place called Mahalo in the neighborhood where I stayed that looked good. You can also try what I had: a vegetarian version at Native Foods Cafe, which is a chain with locations throughout the city.

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The Wormhole Coffee is a funky, chill cafe in Chicago to get a beverage and hang out for a while. I went here to get some work done for 2 of the days I was in the neighborhood. I had a great herbal tea that was ginger and lemongrass based and made from all fresh ingredients. They have a Delorean casually parked in the back!

There was also a nice farmer’s market outside of the Museum of Contemporary Art, where I got a delicious savory crepe by Gotta B Crepes! Their crepese cost about $5-12.

Savory crepe at farmer's market at Museum of Contemporary Art Chicago

Where to stay

I stayed in a hostel called Urban Holiday Lofts, near Wicker Park. It’s everything that I needed as a solo female traveler. The bathrooms were spacious and clean, and the 6 bed female dorm that I stayed is was also pretty spacious and outfitted with lockers and chairs. I paid about $35 per night.

Perks were that it wasn’t a super touristy part of town, and it was near the 606. I didn’t go into the city on one of my days there, and spent it exploring the surrounding neighborhoods on foot. I walked the length of the 606 trail and had some great food at the Chicago Diner.

Other cool neighborhoods to stay in are Logan Square and West Loop.

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Until next time, Chicago!

At this point in the summer, I was craving exploration. I wanted to see some new places and find some favorites. After moving back to New York and settling there for a few months, this was the first new place I’d been to in nearly 6 months. That’s a long time for someone with the travel bug! I was on the lookout for cool vibes in a new environment. Chicago did not disappoint!

I really liked how easy it was to get from the airport to the city. It costs only $5 and takes about 45 minutes. That’s the best I’ve ever seen anywhere! In addition to seeing some new places, I had some time to be alone and think about what’s going on in my life. I also felt really connected to art for the first time in a while.

With the promise of more food and coffee to be found, I know I would like to go back to Chicago for another round. What are your favorite spots in Chicago? What are you looking forward to doing on a long weekend in Chicago?

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Going to Chicago? Save this for later!

Long Weekend in Chicago-min