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, here are a few recommendations for how to plan a perfect weekend in Chicago.

Weekend in Chicago

This is a quick guide for how to plan a weekend in Chicago that covers many of the major attractions, places to see, and restaurants to check out.

Where to Stay in Chicago

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 Monaco Chicago. Located in an art-inspired neighborhood, it’s steps away from award-winning dining, world-class shopping, and the Chicago River.

Where to Eat in Chicago

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.

Places to Explore in Chicago

There are so many iconic spots in the city, but where do you start? I recommend you start the day a Skyscraper Tour 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.

Where to Shop in Chicago

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!

Where to Play in Chicago

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 and has brilliant views of the Chicago skyline.

When you’re done, grab a spot on the sandy beach to relax or join one of the pick-up volleyball games.

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As you can tell, it’s not that hard to have a good time in the Windy City. A weekend in Chicago 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