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Chicago Sightseeing

Chicago in 1 Day

We arrived in the city of Chicago at 9.45 in the morning after an overnight trip on the train from New York. As we only stayed overnight we needed to make the most of Chicago in 1 day. Of course, it involved quite a lot of walking but we fitted quite a bit in. You can get a good taste of Chicago in 1 day although you’ll probably want to come back.

Where to stay

Even if you are only staying 1 night, you still need somewhere nice to relax after a busy day. I chose the Chicago Athletic Association Hotel for its central location. It’s an odd name for a hotel but the Chicago Athletic Association Hotel is named after the sports Center on whose premises it now stands. The hotel is impressive and in a great location, overlooking the park just across from Lake Michigan. The lobby is on the 2nd floor and is a huge room filled with large comfy sofas and decorated like a posh sports club.

Our room was ready early, always a welcome bonus. We stayed on the 7th floor and our room was also decorated with a sports theme. On the way through we spotted some interesting restaurants and bars, including a games room with boules, bar football and a number of other games.

Lake Michigan & The Navy Pier

Chicago in 1 Day Lake Michigan
Lake Michigan

As we only had 1 day in Chicago for sightseeing, we dropped our luggage in the room and headed straight out. We walked across the park to the lakefront. Lake Michigan is so vast it feels like you’re walking along the seafront. As you can see in the photo above, it was pretty cold during our visit. You need to wrap up warm to visit Chicago in January.

Then we walked along the walkway as far as the Navy Pier. This is a popular entertainment area in the summer but it looked to be under maintenance as we went past. In fact, the big wheel had been partly dismantled.

Chicago River Walk

Chicago in 1 Day Chicago Skyline
Chicago Skyline

More by luck than planning, we found our way to the Chicago river and wandered along the riverside, past Trump Tower and the Chicago Tribune. We weren’t the only people walking around but there aren’t many tourists about. Probably far too cold. It was very cool although thankfully not raining.

River Walk
River Walk

Ride the ‘L’ train

The 'L' Train
The ‘L’ Train

Anyone who has watched all 15 seasons of ER will know that the ‘L’ train features frequently so we were determined to take a ride. This is an elevated train which loops around the centre of Chicago. We took a short trip on the brown line just to do the loop section. You get a good view of the many bridges over the river as well as some of the skyscrapers which make up the iconic Chicago skyline.

Chicago Art Institute

Chicago Art Institue
Chicago Art Institue

The Chicago Art Institue is located in Grant Park which was just outside our hotel. It’s one of the oldest art museums in the USA so well worth a visit for art lovers. Even if you don’t venture inside, take a look at the bronze lions which sit outside the main entrance.

The Windy City


Chicago is known as the windy city and we arrived prepared for icy, and of course, windy conditions. On our last round-the-world trip we marvelled at the lack of rain we encountered. The first sign of rain didn’t occur until we sailed into Ketchican, Alaska, more than halfway through our journey. So we crossed our fingers crossed for dry weather this time also. It certainly looked promising as Chicago was not only rain-free but spectacularly free of wind too.

As we headed out the morning sun was shining brightly but do not get me wrong. It was not warm, there was an icy chill in the air and coats so hats and gloves were absolutely essential for survival. Paul forgot to bring any gloves and although I did offer him my spare pare they are apparently too pink for him and so he walked around gloveless with his hands firmly stuffed in his pockets except when braving the elements to take a quick photo. Even the camera baulked at working in the cold and its batteries had to be coaxed back into life in order to record some more images of the Chicago skyline.

Of course, ice can be a real problem in a city with such tall buildings. These amusing signs are a cool way to remind pedestrians to be careful of falling ice shards.


Grant Park

Grant Park
Grant Park

One thing is for sure, Chicago is not full of tourists in January.  It is not full of anyone. Even the traffic seemed light and well managed. Particularly in comparison to New York’s chaotic streets. We had the park pretty much to ourselves and although that sounds a bit creepy, it really wasn’t. Despite its somewhat shady reputation, it actually feels pretty safe, looks very clean and probably deserves a higher position on the tourist trail.

Statue of General Logan

General Logan
General Logan

We wandered past the statue of General Logan (who fought in the Civil War) positioned on a hill which affords views of Lake Michigan and the Metra light rail which runs alongside the park.



A more modern art offering can be found slightly further on. Agora (from the Greek for Urban Meeting Place) is a collection of headless, armless statues by a Polish artist, Magdalena Abakanowicz.

In Summary – Chicago in 1 Day

Chicago in 1 Day River Wak
River Walk

So, in summary, that’s what we fitted into Chicago in 1 day. Of course, there’s a lot more to see here. However, everything we did was within walking distance of our hotel. So it’s an easy and cheap way to sightsee and gave us a good introduction to the city.

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