In this guide, we’re going to share with you our suggestions for how to spend two days in Chicago.
As the third largest city in the USA, there is a lot to do in Chicago. There are world-class museums, a great selection of attractions, and some foods you just have to try.
There are also cultural sights, from first-class performance venues through to architectural history. Those of you visiting Chicago with family are also going to find plenty to keep you all entertained.
We have visited Chicago a number of times and always enjoyed our visits. Some of the museums in particular are absolutely world class, and of course we love the food!
As well as a detailed two-day itinerary for Chicago, this guide will also contain tips on where to stay, how to get around, how to save money when you’re in Chicago, tips on when to visit, and lots more. Let’s get started!
2 Day Chicago Itinerary
Our suggested two-day Chicago itinerary has you visiting the city’s top sights and attractions. This will have you seeing the main highlights of the city and visiting its most famous attractions and museums.
It’s a busy couple of days, and as with all our itineraries, we recommend you use it as the starting point for your planning. Feel free to add and remove items depending on your own interests and travel style.
Chicago Day 1
Your first day in Chicago has you going to the top of one of the world’s tallest buildings, learning about architecture, seeing a Chicago icon, and taking in some stunning art.
To get around, most of the sights on today’s part of the itinerary are within around 20 minutes’ walk of each other.
Of course, if you’d prefer not to walk, there’s a range of public transport options available, as well as a Hop on Hop off bus (included on the GoCity Chicago Pass).
You can see more about getting around Chicago in a later section of this guide. Let’s get going with day 1!
Skydeck Chicago at Willis Tower
When we visit a city, I always love to get a bird’s eye view of it if I can to get a feel for the layout. One of the best places to do that in Chicago is at the Willis Tower (formerly known as the Sears Tower).
This massive 108 floor skyscraper dominates the Chicago skyline. When it was completed in 1974 it was the world’s tallest building, a title it held for almost 25 years.
It was originally known as the Sears Tower and the lower part of the tower was the headquarters of the retail company Sears. It was renamed in 2009 to the Willis…
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