(Last Updated On: November 26, 2023)

Due to a last minute change in plans I found myself with about 16 hours in Chicago between arriving on the California Zephyr Train and flying to Washington DC. I knew I’d only have a few hours of daylight to see something on a Sunday late afternoon so I scanned the internet looking for something fun. I’d never been to Chicago before, and though I love cities for some reason didn’t have a strong desire to go there. I’m happy to say that my brief visit changed my mind and now I’m excited to go back for a longer time someday!

Read on to get the scoop on what to do for a short time in the ol’ Windy City!

The Navy Pier

I settled on the Navy Pier. It’s one of Chicagos top attractions with events, culture, dining, shops, views, and a small amusement park.

Bob Newhart Statue

This made me way more excited than it probably should have 😀 ! I was delighted to find out that the Navy Pier hosts a statue of legendary comedian Bob Newhart! It’s down near the end of the Pier. A couch is next to Bob so you can sit down and spill your guts to him. I remember spending many Saturday nights as a pre-teen watching the great line-up of Mary Tyler Moore, Bob Newhart and Carol Burnett. Ah, those were the days!

In case you don’t recall, in the 1970s Bob Newhart had a long running sitcom on CBS. He played a psychiatrist who lived in Chicago, and the opening montage features him leaving his office then traveling by train thru Chicago to his apartment home. Check out this funny article about how the route Bob takes in the opening makes no sense if you know anything about Chicago.

Strangely there is no sign or plaque with the statue. When I found it a teenaged girl was laying on the couch. I excitedly asked if she’d mind taking my picture there. She said, “You know who this is?” I explained the brilliance of Bob to her (as her friends giggled off to the side). She replied, “Oh, I thought it was a President or something.” 😀


The Navy Pier has many restaurant and bar options, including about 10 sit down restaurants. I was really intrigued by one, the Offshore Rooftop. It is the nation’s largest rooftop venue with stunning panoramic views. However, when I went up to check it out I was already pretty hangry, and it turns out to be one of those “loud restaurants”. The views and looks of it were very appealing, but if, like me you’ve gotten to the age where noisy restaurants bug you it might not be your top choice either.

I ended up eating at my hotel’s Spanish restaurant, Lirica. The food was wonderful and the noise level just right for Goldilocks (me).

Sable Hotel (by Hilton)

The Pier’s sights, views and food were great, but the best part of my brief Chicago stay was my hotel! I booked this because it was on the Pier, had good reviews and was only $200 per night. When I entered my room I was stunned by the incredible floor to ceiling windows offering amazing city and Lake Michigan views! I think I probably lucked into a low rate on a slow day, but honestly I think the room/ view was worth way more than $200. Very comfortable bed and sheets! I recommend highly!

Final Thoughts

I found my brief stay in Chicago surprisingly wonderful! I’d love to go back and get to see more of the sights and to explore the amazingly huge Lake Michigan! Also, though it was a nice, warm day (around 75 degrees) it was indeed WINDY!

The Navy Pier is about a 15 minute cab ride from Union Train Station, and 50 minutes from O’Hare International Airport.

Please let me know if the comments if you have any recommendations of what to see in Chicago! Thanks for reading!