What To Do With Only One Day In Chicago

What To Do With Only One Day In Chicago

One day in Chicago only to go see all the sights?

With only a three-day visit  and only one day in Chicago as a tourist, I wondered how I could possibly narrow it down with all that there is to see in the windy city. I traveled specifically to Chicago for a Mastermind conference over a weekend and arrived on Thursday afternoon to allow at least one day to become acclimatized, both to any jet lag I might have had (and I did) and also to the colder weather.

Before I set off on the trip I decided I’d wait until I reached Chicago as I wasn’t really sure what to expect. After 24 hours of travel and the double white knuckler landing (Yes I was on that flight!) I am really pleased I did wait.

By the time I reached my accommodation on Randolph Street it was time for a spot of dinner, a bath and bed to sleep hopefully. I won’t bore you with the jet lag details!

With a few hours sleep I set off in the morning after asking the way to Millennium Park and to find the stop for the big double decker bus to take a tour of city, get my bearings and make the most of one day in Chicago.

On my way there I came across the Chicago Cultural Center  where there was visitor information. The people there were very helpful and handed out maps that I used throughout the day.

Directions are not my strong point 🙂 and I couldn’t find the bus stop for the bus where the gentleman had directed, so I walked to Millennium Park instead. It was a beautiful park with the fall colors on the leaves highlighted and the art that dotted the landscape throughout the park.

Millennium Park Chicago


One of the main attractions at Millennium Park is Cloud Gate or as it’s known by it’s nickname “The Bean” It is a sculpture that resembles the shape of a kidney bean and is made of polished stainless steel. People are fascinated with the attraction as it’s highly polished surface acts as a giant mirror!

Cloud Gate, AKA The Bean

 As the sun shone brightly after a stroll around the park, I looked to the guide to find the highest building so I could have a birds eye view of Chicago. 360 Chicago (formally known as Hancock Observatory) was the destination straight up Michigan Avenue also known as the Magnificent Mile as the who’s who of the fashion world line the streets.

Time permitting I would have happily spent the afternoon checking them out, some of the window displays looked so inviting! The streetscapes were full of living color with highlights of causes local to Chicago.

Michigan Avenue Chicago One day in Chicago


I strolled past some famous landmarks that you would recognize.

Trump Tower

After a good 1/2 – 3/4 hour walk I reached 360 Chicago and I wasn’t disappointed, the views from the 95th floor are pretty spectacular!

View from 360 Chicago

The cost to visit is $18 and here’s a hot tip if you don’t want to spend that sort of money, the restaurant and bar on the 96th and 97th floors are free to enter, however, you wouldn’t have the benefit of seeing the whole 360 of Chicago and I’d highly recommend it!

360 chicago Looking towards Navy Pier

Once the sightseeing was over and I hit the street I decided to head back to my hotel. Within about 1 1/2 hours I was in the building the sun had completely disappeared and the windy city was starting to live up to its nickname!

If you have any questions about what to do with only one day in Chicago, head on over to my Facebook page where I hang out every day and I’d be happy to answer them, or ask in the comments below.

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