Monday, March 7, 2016

City Guide: Chicago, IL

In the beginning of October, I flew out to Chicago for a quick weekend trip. Honestly, I love the short, two day trips more than spending an entire week exploring a new city. This forces me get the day started early, plan out my itinerary, and be as strategic as possible. Below are some of the best places I found while I was exploring Chicago. I still can't believe how much I was able to explore in such a short window of time!


My first AirBnB experience was when I went out to Chicago. It was a bit of a last minute trip so hotels were a little pricey and I wanted a more authentic experience; I really wanted to feel as if I was living in the city for the weekend. I really believe the best way to see any city is through the eyes of a local and my host provided excellent recommendations which really made my trip special.

I stayed in the Lakeview section of the city which reminded me a lot of Fairmount in Philadelphia, PA {where I currently reside}. You were able to walk around to many different restaurants,bars, shops and the location was pretty close to Lake Michigan as well. It was because of this trip that I decided to use AirBnB when I went to Miami in February.


Pequod's Pizza
Prior to this trip, I had never had deep dish pizza. I had done a lot of research and narrowed it down to two places. How did I decided on Peqod's? Well I asked my waitress at lunch earlier that day for a recommendation and she raved about this place. The place was pretty crowded and they do not take reservations but I was able to grab at drink at The Drinkingbird {located next door} while I waited. When it came time for pizza, I was starving and couldn't wait to give it a try. It was good, but extremely filling. I could barely eat two slices! It was worth the experience, but I still prefer my New York style pizza.

Heritage Bicycles
I stumbled across this coffee/bike shop when looking for an afternoon pick me up. It is such a unique concept; the store sells and repairs bicycles but also has the most adorable coffee shop I have ever seen. I had a cup of their pour over and brought my coffee {and pastry} outside to a bonfire they had set up adjacent to the store. It was such a great experience and I was so happy to find this hidden treasure.

S&G Restaurant
If you are a fan of diners, endless coffee and a big breakfast then I recommend you make your way here if you are ever in Chicago. I had breakfast here both days of my trip. The staff was extremely nice and you could tell there were a lot of regulars coming in for breakfast, which is always a good sign of a great restaurant.

Local Root
I stumbled across this place accidentally when I ended up getting lost on a walk, but after reading the menu I decided to stop in for lunch. Everything at Local Root is sourced locally and they are a no-waste restaurant. I was having such a great time talking to the staff that I decided to stay after lunch for a few beers. Everyone was so friendly and the food was extremely fresh and delicious.


Architectural Boat Tour
If there is one thing that you have to do while visiting Chicago, it is this boat tour. The city looks absolutely spectacular from the river and the tour guide I had was wonderful and funny. It was not only fun, but educational and informative as well. I left having a greater appreciation for architecture and a better understanding as to why some buildings look a certain way.

Lake Michigan
As a first time visitor to the Midwest, I was pretty excited to get to see one of the Great Lakes. Chicago sits right along Lake Michigan and it is quite the sight. The weather was pretty warm the weekend I was there so the river path was filled with runners, walkers and bikers. I was glad to experience the beautiful scenery and enjoy a long walk prior to leaving for the airport.

Lincoln Park Conservatory
I accidentally stumbled across this place after checking out The Lincoln Park Zoo {which is free if you are interested in exploring the Zoo}. The Conservatory was stunning with different rooms filled with ferns, flowers and palm trees. There is also a large lawn right outside of the entrance where many people were reading and playing board games with friends that day.

Other Notables: The Bean, The John Hancock Building, The Magnificent Mile - Michigan Avenue, Navy Pier, Wrigley Field

Interested in more City Guides - Check out my Miami Beach Guide, Philadelphia Food Guide and Hoboken Food Guide