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How To Plan a Great Weekend in Chicago

How To Plan a Great Weekend in Chicago

Chicago, famous for so much more than its winds, is the quintessential American city. Whether you’re a foodie, an adventurer, or a purveyor of the fine arts or are just looking to have a good time, you have plenty of options to choose from. If you only have a weekend to spare and are looking for a few quick suggestions for what to add to your itinerary, let me tell you about all the hot spots to experience the city.


Image via Flickr by mighty.travels

The first thing you’re going to want to do is find a great hotel in Chicago. One of my favorites is the Kimpton Hotel Palomar Chicago, which was voted in the top 20 of hotels in Chicago for 2016 by U.S. News & World Report. Located in an art-inspired neighborhood, it’s steps away from award-winning dining, world-class shopping, and the Chicago River.


Image via Flickr by Leandro’s World Tour

From the hottest celebrity chef restaurants to local grub, Chicago has food to suit all taste buds and appetites. There are 24 Michelin-starred restaurants in the city, which means that Chef Grant Achatz’s take on molecular gastronomy is within reach at Alinea. On the other end, you have the many restaurants that cater to Chicago’s specialties of Italian beef, hot dogs, and pizza. At least one of your days in the city has to include the world-famous deep-dish pizza at either Gino’s East or the original Pizzeria Uno. You really can’t be blamed if you spend the weekend eating.


Cloud Gate Chicago

Image via Flickr by Timothy Neesam (GumshoePhotos)

There are so many iconic spots in the city, but where do you start? I recommend you start the day with the 10 a.m. Historic Downtown: Rise of the Skyscraper run by the Chicago Architecture Foundation. This will walk you through some of the city’s oldest tall buildings and give you a new appreciation for the skyscraper revolution. From here, make your way over to the Art Institute. Just north is the famous Millennium Park and the shiny sculpture affectionately called the Bean. Round out the day with a stroll on Michigan Avenue Bridge and the Magnificent Mile before making your way to the top of the John Hancock Center to see how far you’ve come.


Image via Flickr by David Hilowitz

Shopping until you drop is certainly an option with Chicago’s wealth of trendy boutiques, luxury, and art shops. Your best bet for a unique experience is to make your way to Wicker Park and Bucktown, where you’ll find the likes of Futugarb for clothing, Myopic Books for used books, Cat and Mouse Game Store for board games, and Reckless Records for music.  After your time here, you may leave with a lot of bags in your hands!


Image via Flickr by romanboed

If you have the itch to be active, head over to North Avenue Beach and rent a bike. This sprawling beach stretches miles and hugs the Lake Michigan coastline. When you’re done, grab a spot on the sandy beach to relax or join one of the pick-up volleyball games.

As you can tell, it’s not that hard to have a good time in the Windy City. A weekend is certainly too short, but that just means that you’ll have a reason to come back. Make the most of it, and when you’re back home, start planning your next trip!

Featured image via Flickr by MPBecker

About Will Tang

Will is a travel blogger writing for Going Awesome Places. Since quitting his consulting job in 2012 he's been travelling the world and along the way writing about his epic adventures and taking amazing photos. His true passion lies in telling stories, inspiring others to travel, writing detailed trip itineraries for others to follow and providing helpful tips and tricks to travel better. Also the founder behind Travel Blog Breakthrough and freelance writer for Hipmunk and currently working on the #‎HipmunkCityLove Project.

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