Staycation at Historic Millennium Knickerbocker: A Chicago Classic

Staycation at Historic Millennium Knickerbocker:  A Chicago Classic

I get it – I love to get away. But sometimes getting away is a martini, a nice bubble bath and a new comfy bed for the night. Staycations have become more popular over the years and I can see why – yes, its fun to explore a new city, but sometimes a nice night in at a nice hotel is the self-care and break girl bosses need. I recently had a nice Chicago staycation at the historic 1927 Millennium Knickerbocker Chicago.

And if a staycation at this historic hotel isn’t enough, it’s right by Michigan Avenue, 360 Chicago Observation Deck at John Hancock and the Museum of Contemporary Art for you to explore some of Chicago’s most iconic – and if you’re a native – overlooked spots.

The Knickerbocker History: Speakeasy and Playboy:

I think one of the coolest aspects of the hotel is its history. Anyone can build a new hotel, but you can’t make up this hotel’s sinister past. I had to see for myself the Penthouse floor where Al Capone’s brother once ran a casino and speakeasy. Today it’s used for conferences or events but you can still see the cutout to a secret stairway that guests used when the cops came. Al Capone’s brother was never caught because everyone would use that stairway to go down a few flights of stairs.

The Knickerbocker also had a few ownership changes throughout its nearly 90-year history. In the ’70s, the property had a stint as the Playboy Towers. The hotel has housed such luminaries as John F. Kennedy, Richard Nixon and the Rolling Stones.

The Rooms:

The hotel still has a historic feel. The over the top chandeliers are all noticeable about this four star hotel.

There’s definitely an older feel, but the rooms have been updated and transformed into spacious one bedroom suites with a mini bar, a whimsical bed, 40″ flat screen TVs, and yes a bathrobe and yes – a whirlpool tub (make sure you get the room with a whirlpool tub, you’ll thank me later).

I took a quick 5-minute walk to Water Tower Place on Michigan Ave to go to the new Millennial makeup store, Riley Rose. Since Lush is no longer at Macy’s, Riley Rose was perfect for picking up a bath bomb.


I loved the hotel room which had its own living room and a private bedroom and expansive bathroom.

One of my favorite parts of a staycation is getting ready, and I appreciated the lighting and added mirrors. My friend met me for dinner so we got all dressed up to have martinis – something that we should do more often.

The Martini Bar:

One luxury of a Chicago Staycation is that you get to enjoy fine dining and drinks. One of the nice things about the Knickerbocker is that right in the lobby is the Martini Bar open till 10 pm for dinner and 12 am for drinks.

Its extensive martini list is to be explored and enjoyed, and despite being served at the bar, it’s fine dining cuisine is exceptional. Plus, they have a piano and some live entertainment on certain nights.

martini bar

I’ll start with the food. If there is one thing you should order, it’s the steak and arugula salad. Honesty, it’s the best salad I’ve ever tasted. The dressing was light, the steak was savory and the arugula was fresh and had some added toppings for a slight crunch.

And since we had a late night meal, my friend and I also tried some of the martinis. Hands down, the chocolate martini was my favorite. I usually love a dirty martini or a Cosmo. Those were strong and really great but there was something about the chocolate martini.

Sweet Dreams and Healthy Breakfast:

I took my martini up to my room and drew myself the most amazing bath. The bathroom at The Knickerbocker is over the top. They have a shower area and a separate bathtub in the room. I added the jets to the bath and it was better than a jacuzzi at most hotels.

In the morning, I woke up in my robe and comfortable king-sized bed. I connected my phone to the TV to get ready to my favorite music and then rushed downstairs for some much-needed coffee and a delicious omelet at Nix, the other restaurant in the Knickerbocker. The service was great and the omelet was actually delicious, especially the side of bread and jam.


There are so many hotels in Chicago because it’s one of the greatest cities in the world. Honesty, I’ve been to quite a few hotels – The Trump Tower smells like vanilla because of the candles. Cambria in the loop is great for a Theatre District Hotel with the exquisite Italian restaurant, Petterino’s next door, The Palmer House has a beautiful and extensive lobby and a spa but the rooms are a bit stuffy.

But the Knickerbocker, this hotel has history and merit and I was surprised by the quality of the food, the rooms, and the location. The hotel rooms itself were some of the nicest I’ve been in. I would say one issue was that the WiFi went in and out sometimes, but other than that, my stay was perfect and memorable. It’s a good location, a good price and it’s a historic spot you should add to your Chicago Bucketlist.

This article is a sponsored post.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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