A Newbies Guide to Chicago

  • Chicago bulls basketball court during a game

  • dessert taco made out of chocolate at Parlor Pizza

  • high view of the Chicago skyline

  • empanada with avocados, tomatoes and lettuce at Girl and the Goat

  • friend chicken on white plate with buffalo sauce at Celeste

Discover the Windy City
Famously known as the Windy City, Chicago is a great vacation spot featuring breathtaking architecture, unique food, and a bustling nightlife. As a newcomer to the city, I have found some suggestions that will fit the needs of any individual looking to get a great first taste of Chicago.

Devour Chicago
Chicago has a very creative selection of restaurants catering to a variety of taste buds. Bring your adventurous palette to the West Loop for a vibrant food scene.

Girl and the Goat
This new American restaurant is part of a trio that will have your taste buds ringing. The Wood Oven Roasted Pig Face is a must! This dish is paired with an egg sunny side up, tamarind and potato stix that combines a mixture of amazing flavors. The Goat Empanadas are a staple too. Reservations are recommended.

This Mediterranean inspired restaurant is cozy and calm, while the food gives off an extremely bold impression. My favorite on the menu is the Chorizo Stuffed Medjool Dates, which are wrapped in bacon. This is the perfect combination of salty and sweet! Pair this with a glass of red wine to complement the flavors.

Parlor Pizza Bar
Yes, Parlor Pizza Bar is known for their delicious pizzas, but there is one thing that I love even more; their taco desserts. These “Tacolatos” are the perfect end to a meal. The Go Nuts taco is crunchy and sweet with Nutella, Ferrero Rocher and Chocolate Gelato, all in a waffle shell.

This South American restaurant is a must! If you are looking for great food, drinks and a show, this is the place to go. Watching trapeze artists while drinking a Flaming Margarita is a great way to start off the weekend. The Lechon Asado, pork shoulder with Chicharrón, was juicy and tender.

Explore Chicago
Chicago is home to amazing architecture, sights, and sports teams.

  • The architecture tour is a great way to learn about Chicago’s history, travel through the river and see the incredible buildings.
  • Millennium Park is a perfect spot to walk around and see the famous bean!! They also host many free events during the summer.
  • If you want a view from above, check out the Willis Tower for something one-of-a-kind.
  • This is a great destination for sports fans year round. Chicago is home to many teams including the Cubs, Chicago Bears, Chicago Bulls, and the Blackhawks. Plan on attending a sporting event at United Center, their website is up to date with all of the available events.

Socialize in Chicago
Chicago has many areas with a vibrant nightlife. Whether you want to throw back a couple of drinks, or dance the night away, there’s something for everyone.

  • Joy District is a multi-level bar located in River North that is perfect for dancing to upbeat music.
  • The Blind Barber is a hidden gem in the West Loop, known as a barbershop during the day, but converts into a 70s themed bar at night. The cocktail list is amazing.
  • Celeste in River North is a very versatile bar. With three floors that range from a classy bar, a disco floor, and a rooftop; this place fits everyone’s mood. Fun fact: they have great fried chicken.

Experiencing the Windy City
Whether you’re into food, attractions or nightlife; Chicago has a lot to offer. These suggestions only give a small glimpse into a newbies guide to Chicago. There are plenty of other great options out there that will fit your needs, just remember to reserve ahead and go in with an explorative mindset!

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.

Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.

This post was written by Hilton Suggests Team Member, Nidhi S. 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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