A Weekend in the Windy City

  • Night view of skyscrapers in Chicago

  • close up of food

  • Night time view of the chicago river walk

  • opalescent panels line a sidewalk

  • colorful panels

  • Large blue ferris wheel over a lake

  • blue skies over the Chicago Skyline

  • Beer taps shaped like geese

  • colorful pasta behind a glass case

  • close up of food

For someone who loves architecture and delicious food, Chicago is a great destination for both. This city offers buildings with stunning features, a clear blue lake, food, breweries, shopping, comedy, and so much more.

Eat and Drink your way through Chicago

  • Stan’s Donuts – If you are looking for a good cup of coffee or a tasty donut, I would go to Stan’s. This coffee shop offers delicious pistachio donuts and draft coffees. For someone who is not a coffee drinker, I was very pleased with their draft vanilla latte.
  • MFK – The drummer that started MFK has created a unique eating experience with a Spanish seafood-themed menu designed for sharing. Don’t let the exotic menu intimidate you, the staff is extremely knowledgeable and will help assist you in selecting plates to order. I highly recommend ordering the ceviche, anchovies and seafood cataplana.
  • Goose Island – This brewery is best known for their bourbon barrel beer and IPA. Their tour was extremely informative and I was happily surprised when I learned something new on this tour. During the tour, they go into detail about the history of bourbon barrel beer and the brewing process for sour beer. My favorite brew is 312 and Dooley Dry Stout.

Shopping for Souvenirs and Yourself

  • Eataly – I could have spent all day here at this Italian grocery store and eatery. They have everything from basic cooking essentials to fresh squid ink. Their freshly made pasta makes for a great gift to bring home to your friends and family. My family and I really enjoyed their red wine and pork ravioli.
  • Crossroads Trading Company – This resale store is a great place to find name-brand items for a fraction of the price. They had everything from Lucky Brand jeans for $10 to Kate Spade handbags for $20. For a girl from Texas where I have a hard time finding cool winter apparel, I was in heaven and had hard decisions to make in figuring out how many clothing items I could cram into my carryon!
  • The Magnificent Mile – Now if you are looking for a shopping experience like 5th Avenue this is the place for you. There are over 460 retailers to choose from and all conveniently located on the bus route so you will never have to walk far from one store to the next.

Instagram-Worthy Spots

  • Navy Pier – The Navy Pier is a great place to enjoy views of Lake Michigan and of the Chicago skyline. I highly recommend taking the ferris wheel to take in the best views of the lake and the city, tickets are only $13 at the pier. Keep an eye out for the art installation Prismatica located at the entrance of the pier. The installation includes 25 prisms creating a kaleidoscope of colors.
  • Michigan River – There are two ways to enjoy one of Chicago’s most iconic views of the Michigan river and the buildings that border it. The river walk provides you with the opportunity to get your steps in alongside the river. However, the rooftop view was my favorite between the two. During one of my evenings, I took in the view of the river from the rooftop bar at London House.

Come and See all Chicago has to Offer

I recommend doing some research before visiting and make sure you pack the right clothing. The wind coming off the lake can be very chilly in the winter months. There is so much to do and see in Chicago and my suggestions don’t even scratch the surface of what this city has to offer. This is a city where you can plan out your activities in advance or the day of, whichever you prefer. There is so much to see and do in Chicago all year long.

To access more information about local restaurants, unique attractions, and special offers in Chicago, visit our Destination Guide, or explore Hilton properties in Chicago below.

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Night view of skyscrapers in Chicago

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This post was written by Hilton Suggests Team Member, Ara O. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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