Trip Recap: Chicago

The BeanI have now visited Chicago five times and I can proudly say I’ve done about every touristy thing on the list. This past weekend I travelled up to the windy city once again for my best friends’ wedding and was delighted to show my boyfriend around the exciting town for the first time. Deep-dish pizza, The Bean, The Signature Room, Portillo’s hot dogs, and sprinting to make the train are just a few highlights!

Chicago is such a unique city filled with amazing shopping, decadent food, and a gorgeous lake front skyline. Navy Pier can provide that nostalgic child-like feeling as you circle around the ferris wheel overlooking the city, deep-dish pizza might be the richest slice you’ve ever experienced, and your pockets will empty walking down Michigan Avenue once you see the multi-level story buildings packed with every retail and designer store possible.

I’ve visited in Winter and Summer and I have a hard time choosing which one I enjoy more. Winter is frigid, but if you know how to properly dress, it can be a really fun experience. Chicago’s most popular sculpture, The Bean, sits in the middle of Millenium Park. In the Winter, the park is home to a huge ice rink in the most beautiful part of the city. Grab a cup of hot chocolate and watch the snow fall before you head back to warm up inside the 9-story flagship Macy’s on State St.


My favorite part about Chicago is obviously the food though. You can’t pass up the opportunity to experience deep-dish pizza at Giordano’s! The pizza takes 45 minutes to bake and comes to the table like this:

DSC_6248_640One piece of deep-dish is like 3 pieces of normal pizza, so pace yourself. If deep-dish isn’t your thing, there is also an abundance of incredible italian food all over the city. Flatbread pizza and wood-fired pizza are other options you can find around town. If Italian food is what you’re looking for, a stop into Eataly should definitely be on your list. Eataly is a 2-story Italian market place filled with meats, cheeses, bread, gelato, wine, pizza, olive oil, and a nutella bar! Spend the whole evening wandering around trying cheese boards, ordering a pizza, having a wine-tasting, and experience the best lasagna I’ve ever had in my life.


The other Chicago staple is Portillo’s Hot Dogs. Of course we stopped in to get one of their famous Chicago dogs topped with mustard, relish, tomatoes, peppers, and a kosher pickle on a poppy seed bun. Pick up a slice of their chocolate cake while you’re there; it has mayonnaise in it!! They also have a chocolate cake shake that I’ve heard is INSANE.


If it’s cocktails you’re looking for, I stopped into a tiki bar called Three Dots and a Dash when I was in town a few weeks ago for my friends’ bachelorette party. This is a very hidden bar that has some of the craziest drinks I’ve ever seen. There is one that is $385, shaped like a treasure chest, comes to the table smoking from dry ice, AND on fire! My favorite drink was the banana daiquiri because of the dolphin-shaped banana that comes atop of the drink.


Our main priority was to visit the 95th floor Signature Room in the John Hancock Building. Technically, the 95th floor is a restaurant that has floor to ceiling windows that wrap around the entire floor overlooking the whole city. It’s breathtaking. Normally overlooks of the city cost money to wait in a line and stand at the top, but the Signature Room only requires you to order a cocktail at the bar! What a deal. You’ll probably be thirsty from all the walking you’ve been doing anyways. Tip: the best view from the 95th floor is in the ladies’ restroom!


This truly is an incredible city to visit for a while. There is so much more to do than you expect! I would check out kayaking the river around the city if you have time. Ever since I saw this article in Cooking Light, I’ve wanted to try out this active day in Chicago! Unfortunately, we only had a few hours in the city but I wanted to share this picture incase any of you plan to visit and need some healthy and fun things to do in town.


Until Next Time,


Extra food and bar photos courtesy of,, and

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