Travel Diaries: 72 hours solo in Chicago

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Chicago
Photo courtesy of Hannah Koehler

When the holiday season ended, I was not looking forward to the unfortunate lull of mid-January before the semester started. On a whim, I decided to book a train ticket and spend a few days in Chicago, Illinois. Chicago in January? Yes, a rather bold choice. However, the weather played in my favor and it averaged between 30 and 40 degrees, rather mild for the Midwest. I had not taken the train to Chicago before, but it seemed like the better alternative to driving eight hours alone. The train was a lovely new experience and was affordable and convenient. I booked my ticket through Amtrak, and it was a direct route at the cost of $140 roundtrip. If taking the train, I’d suggest spending your time in the viewcar located in the middle of the train. With large windows and comfortable chairs, it is an excellent spot to drink coffee, read and watch the sunrise. 

Chicago is the third largest city in the United States and has something for everyone. I have been to Chicago a few times now, but I find something new to love every time I go. Chicago is wonderful for a trip with friends as well as solo travel. One of my favorite parts of traveling by myself is that I don’t have to oblige anyone else’s itinerary. No compromises, thank you very much. My 72 hours in Chicago primarily consisted of coffee shops, museums and bookstores because that is how I like to spend my time. If you want a tourist attractions of Chicago guide, I cannot help you. Try Yelp. 

Chicago has many vibrant neighborhoods. When I travel there I like to pick a couple neighborhoods to primarily explore. On my recent trip I spent most of my time in Wicker Park, Lincoln Park and Downtown. 

Neighborhood: Wicker Park/Bucktown

This artsy and bustling neighborhood has ample coffee shops, bars, restaurants and boutiques at your fingertips. 

  • Volumes Bookcafe: I could – and did – spend a long afternoon here. With comfortable seating, the latest books and a coffee shop inside, Volumes has a pleasant and relaxed atmosphere.
  • Big Star Tacos: This place has some seriously exceptional tacos. I ordered the Pescado Taco and the Tostada Coles de Bruselas Taco. The Pescado Taco was a battered fish taco with chipotle mayo, red onion, cabbage, lime and cilantro. The Tostada Coles de Bruselas Taco was a fried brussel sprout taco with refried beans, poblano crema, queso cotija and cilantro. It was a trying time to pick which tacos because the whole menu boasted of fresh and delicious options. My tacos were excellent though, and I would order them again.  
  • Myopic Books: A little bit of a labyrinth, this used bookstore is somewhere I would be delighted to be lost in. 
  • The Goddess and the Grocer: With a delicious, fresh and organic menu, The Goddess and the Grocer is an excellent spot for sitting and staying awhile in their upper level outdoor patio or for food to go. This tiny grocery store and restaurant has sandwiches, soup, pastries, coffee, a salad bar and a large selection of prepared food. It was a chilly day when I went, but their matzo ball soup was exactly what I needed. You can get a cup of soup and a half sandwich for $9. However, this is also the kind of place where you may accidentally buy a fermented drink that costs $10. Maybe not you, but I unfortunately did. The lemon lavender drink was delicious, but for $10 I should have developed superpowers or something. Alas, no such luck. However, the soup and sandwich were excellent. 

Neighborhood: Lincoln Park 

This neighborhood is full of charm and personality, and you can have a lovely time while spending very little money. I loved just walking around and looking at the architecture. Beautiful, old brick buildings are juxtaposed with sleek, modern apartments. If you are the homeowner who saw someone taking a picture of your house, it was me, and I am sorry. 

  • Lincoln Park Conservatory: Near the shore of Lake Michigan, this beautiful botanical garden and conservatory is free of charge and a tranquil respite. 
  • Lincoln Park Zoo: This is a classic way to spend a day in Chicago. This Zoo is completely free and offers some lovely views of Chicago. The Nature Boardwalk at Lincoln Park Zoo offers a nice jaunt with a good photo op of the Chicago skyline. 
  • La Columbe: This coffee shop has several different locations throughout Chicago. La Columbe serves house-brand artisanal coffee, pastries and snacks in a sleek and quiet space. It is an excellent place to stop for a break from walking.

Neighborhood: Downtown

Here is where you come to stare toward the sky and appreciate the dynamic architecture. From art museums, bars, restaurants, coffee shops and shopping, Chicago’s downtown lacks nothing. 

  • The Art Institute of Chicago: A trip to Chicago isn’t complete without a visit. Every travelbook of Chicago will tell you to go here, and they are right. It is magnificent. It is one of the oldest and largest museums in the United States. The impressionist wing is absolutely gorgeous. I wandered around for three hours, and there was still so much more to see. Also, it is in Millennium park, so if you need to grab a mirror selfie at the Bean, it is quite close. 
  • Hero Coffee Bar: If you need coffee before – or after – a visit to the Art Institute, Hero Coffee is a quick walk from the museum. Tucked in a little alleyway with lights strung up, Hero Coffee Bar is a tiny establishment with top-notch coffee options. 
  • The Dial Bookstore: Located on the second floor of the historic Fine Arts Building, this bookstore is stunning. Flooded with light from the large windows overlooking the busy street, the Dial offers a selection of used and new books. After perusing a while, I sat down on the window seat and probably could have spent all day there.

Outside of the neighborhoods I explored, I also recommend these spots: 

  • Chicago French Market: Don’t miss this collection of more than 30 local vendors where you can find food from around the world. This multi-vendor food hall has stalls full of French fare as well as vendors from Chicago’s melting pot of neighborhoods. When I was there I got sushi, a freshly made empanada and a lavender macaroon. I regretted nothing. 
  • The Allis: Make sure to stop by this lounge and bar in the Soho house. Located in a stunning building with incredible architecture, it is an ideal and relaxed space for quick bites and coffee or tea trays and dessert platters. 

Chicago truly has something for everyone and is either a quick 1.5 hour flight or eight-hour drive or train ride from Kansas City. With stunning architecture, a vibrant arts scene, beautiful parks and excellent food, Chicago is my favorite getaway.

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