An Overnight Layover in Chicago

I hadn’t planned to spend the night in Chicago. But when my travel plans shifted last minute, I found myself with a 16-hour layover between arriving on the California Zephyr train and a flight to Washington D.C. As a solo traveler that kind of unexpected window can feel more stressful than exciting, especially in a new city. Where do you go? Will you feel safe? Will you even enjoy it? What WILL YOU DO?

I wasn’t sure what to expect. Chicago had never been high on my list, but by the time I left, I found myself thinking: I can’t wait to come back!

If you’ve got just one overnight in the ol' Windy City, I’ll show you how to make it count. From lake views and city lights to a hotel I still can’t believe was only $200, here’s how I turned a simple layover into one of my favorite unexpected travel moments.

What to Do on a Chicago Layover: Explore The Navy Pier

I settled on the Navy Pier. When you’ve got about four hours and zero brainpower after a long train ride, Navy Pier is kind of perfect. It’s the Times Square of Chicago, but with lake views and fewer people dressed as Spider-Man.

I wasn’t expecting much, to be honest. I figured it would be touristy, and overpriced. And yes, it was a bit of those things, but I liked it anyway. There’s something about walking along the water with the city skyline on one side and seagulls yelling at you on the other that just works.

I passed families chasing toddlers, teens taking selfies on the Centennial Wheel, and a few couples whisper-fighting over where to eat. It was lively but not overwhelming. I felt totally safe wandering around, and no one batted an eye at a solo woman dining alone.

The real showstopper was the view. Lake Michigan looked like the ocean, I couldn't beleive how big is was, and the Willis Tower (formerly Sears Tower) popped up in the distance like it was photobombing my day.

There’s also the Chicago Shakespeare Theater, a huge modern art sculpture called “Reach” that looks like it’s doing interpretive dance, and just enough snack stands to tempt you without causing regret.

All in all, it’s a low-effort, high-reward kind of place. If you’re jet-lagged, mildly hangry, or just want to feel like you’re in a rom-com montage, this is your spot.

The Bob Newhart Statue: A Couch, A Legend, and a Gen Z Lesson Given

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 scolling her phone. I excitedly asked if she'd mind taking my picture there. She said, “You know who this is?” I gave her a passionate 60-second monologue on the brilliance of Bob Newhart while her friends giggled behind her. She responded, “Oh. I thought he was a President or something.”

Reader, I still had her take the photo.

Even if you aren’t a Bob fan, the statue is a sweet little Chicago Easter egg. And if you are, it’s a very fun place to pause and smile like a goofball at your childhood TV therapist.

Where to Eat without losing your hearing

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 are now your cryptonite it might not be your top choice either.

I ended up eating at my hotel's Spanish restaurant, Lirica. The noise level was just right for Goldilocks (me). I had a lovely solo meal there. The food was delicious, and the volume was at that magical level where you can enjoy a little background beat but still hear your own thoughts. Or your audiobook. Or Bob Newhart reruns. Whatever you’re into.

If you like your meals with a view and a vibe, try Offshore. If you prefer comfort, conversation, and possibly churros, Lirica is your place.

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. Floor-to-ceiling windows offered panoramic views of both Lake Michigan and the Chicago skyline. I just stood there for a full minute, doing nothing but blinking and grinning.

The room itself was sleek and calming with a super comfortable bed, quality linens, and a “wooden-look” shower!

And here’s the kicker, it was just $200. I’m pretty sure I caught a low-rate Sunday night, but even if it were a bit more on a different day, I’d still consider it worth it. Heck, I would go back to Chicago just to stay here again. It turned my quick stopover into a full-on travel memory.

If you’re planning an overnight layover in Chicago and want a place that feels both special and secure, check current rates for the Sable. It might just be your new favorite unexpected hotel.

Why Chicago is now My Kind of Town

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!

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