THE GYPSY TRAVEL DIARY: 4 DAYS IN CHICAGO

October 27, 2017

 

Chicago has always been on my list of places to see so when an opportunity arose to meet up a close friend and former flight attendant colleague I spontaneously decided to book a ticket and spend a few days in the Windy City. 

 

Needless to say, Chicago is an absolutely incredible city and I fell in love with it the moment I got there. There are so many cool sights to see and amazing places to eat (hellooo, deep dish pizza)! The weather was hit or miss, and when it missed I'm talking hard rain and freezing winds, but I'm happy I got to thoroughly experience this city even in the short amount time I spent there. 

 

If you're heading to Chicago, here's a list of all of the things I did during my stay. However this is not by any means an expert guide to touring the city, since I wasn't there long enough, but just a collection of some of my favorite things to see and places to eat.

 

 

 

 

TO STAY

 

I divided my stay into 1 night at the Knickerbocker and the other 2 nights at The Whitehall hotel. Both were located right on Michigan Avenue (The Magnificent Mile), the main street which stretches throughout downtown. A perfect place to be if you want to be in the center of it all with grand buildings housing multi-level shops right outside your door and walking distance to all the famous sights.

 

The Millennium Knickerbocker

 

A landmark hotel which has hosted famous people such as Al Capone, Hugh Hefner, John F. Kennedy, The Rolling Stones and many more. The interior is very 1920's glam and the rooms are spacious and modern.

 

The Whitehall Hotel

 

I really enjoyed this small boutique hotel, which is also directly on Michigan Avenue. It's much smaller and more affordable than the Knickerbocker, however my room was almost just as spacious. The staff is incredibly friendly, forthcoming and if I was to ever visit Chicago again I would definitely return.

 

TO EAT & DRINK

 

With Chicago being the food mecca of the United States, I was excited to finally try Chicago deep dish pizza but also visit some of the non-touristy spots. Each and every listing below I highly recommend and would absolutely go to again.

 

 

Giordano's

 

One of the most popular spots for Chicago's famous deep dish pizza, we went there only minutes after arriving since I was not only starving but dying to know what the hype was all about. It's not your typical sit-down-and-order restaurant as you order your pizza upon check-in. Since the pizza is made to order it takes a while and the line was out the door. Our wait was about twenty minutes (I've heard that's short!) and by the time we got our table and finished our appetizer (get the Garlic Fries with Ranch! Yumm!) our deep dish was finally ready and let me tell you it was SO worth the wait!

 

 

 

 

 

 

 

The Allis

 

By far my favorite restaurant during my stay was The Allis! Located inside Soho House Chicago, the restaurant has a cozy dining room with beautiful chandeliers hanging from an industrial ceiling, exposed red brick walls, group tables, couches and big velvet armchairs. Offering all day breakfast and the most delicious pastry and egg dishes which I'll touch on more in a second. I started my meal off with a latte and an almond croissant which made way for arguably my favorite dish on the whole trip. The Mexican influence in this city cannot be overstated. 

 

I'm so obsessed with avocados that wherever an avo dish is on a menu, I must try it! Their avocado toast is served with poached egg, basil and calabrian chili. WOWZA! By far the most flavorful avocado toast I've ever had and I highly recommend this to anyone who decides to go. It's literally what your avo-dreams are made of.

 

 

 

 

 

 

 

3 Arts Club Café at Restoration Hardware

 

This spot I actually stumbled upon on Instagram. One of my favorite travel bloggers had posted a picture here and I immediately had to put it on my list once I knew I was coming to Chicago. It's located in the center of a six story Restoration Hardware! The whole place doubles as a showroom so all the furnishings are for sale, how crazy is that! 

 

We entered the dining room which is in the center of a winter garden complete with olive trees, a very large water fountain with an equally large chandelier above it.The rest of the space is filled with cute little tables and giant couches, perfect for the brunch crowd. It's truly an experience to dine there and I'm so happy Instagram led me here.

We went early for breakfast and ordered the RH Scramble, which is the most popular breakfast dish on the menu. The custard-style eggs were deliciously served with chives on Texas toast.

 

Do yourself a favor and go early which will give you a chance to enjoy the dining room without too many people. In addition to that, take some time to stroll through the 6 stories of beautiful show rooms - you'll feel like you're strolling through a mansion of a wealthy Chicagoan family. 

 

 

 

 

 

 

The Hampton Social

 

This gem of a restaurant will make you feel like you stepped into a surf club in Montauk . The interior has a nautical theme, and the menu has everything from burrata to seafood. Every evening there is live music and you can sit in different areas of the restaurant to get a different experience. It was one of my favorite parts about the restaurant. 

 

Of course I have to mention the highly Instagrammable, super cute "Rosé All Day" wall, which I bet you've seen on your IG feed before. Make sure to get one of their signature drinks, the Frosé!

 

 

 

 

 

 

Cindy's Rooftop

 

 I received a lot of recommendations to visit Cindy's, a rooftop restaurant and bar, in The Athletic Association Hotel which used to be an 1890's Athletic Club, I decided to grab a drink there while waiting for my boyfriend to arrive from Miami and it was the perfect escape from the loud streets of the city. The options are very good with an extensive menu, huge bar and very knowledgeable staff. 

 

From the terrace we sipped our cocktails while taking in an impressive view of Millenium Park, Lake Michigan, and the Cloud Gate (aka The Bean, which I will go into detail later in the post).

 

 

 

 

 

 

 

The Signature Room at the 95th 

 

Located in the Chicago 360, formerly known as the John Hangcock Tower, The Signature Room offers a restaurant as well as a bar and lounge offering the MOST INCREDIBLE view of Chicago. We decided to go after dinner on our first night and enjoyed cocktails while overlooking the entire city from the 95th floor. An absolute must if you want a great view, however the drinks are pricey. This picture below was taken from our table:

 

 

 

TO DO

 

Apart from some classic must-do's I also added some things to do on a rainy day. Luckily my first two days in the city were very warm and sunny and great for walking around and sightseeing. The last two days Chicago lived up to its name and was frrrreezing and very windy and rainy so I've added some things to do on good and bad days as the weather there can be extremely unpredictable.

 

 

 

Cloud Gate & Millenium Park

 

 

An absolute icon and must-do while in Chicago also known as "The Bean"! Located in beautiful Millenium Park this huge outdoor installations reflects the park and the city's skyline. It's so cool to see and a really great photo-op! 

 

 

 

Make sure to take a stroll through Millenium Park, which offers more art installations and a beautiful view of the high-rises!

 

 

 

 

The Art Institute of Chicago

 

One of the largest and oldest museums in the US, the Art Institute is the perfect place to spend some hours strolling through and see numerous famous paintings by Monet, Van Gogh, Warhol to only name a few. Whatever art you prefer, if old or modern, paintings or photography- you're definitely at the right spot here. Especially great for a rainy Chicago day!

 

 

 

 

 

 

Shedd Aquarium

 

Another place I paid a visit to on my last rainy day in Chicago was the Shedd Aquarium. It's really impressive with plenty of different species and very knowledgeable and friendly staff that is happy to chat about the animals. The entrance fee is quite steep (40$) however I thought it was really worth it.

 

 

 

I hope you enjoyed this list! If you visited any of these places or have any tips for my next time in Chicago let me know in the comments below!

 

xo, S.

 

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