Chicago Staycation at Historic Millennium Knickerbocker

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 Elliott 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.


Rest and Relaxation at the Palmer House

My friend is a workaholic so she decided to book a room at the Palmer House and bring me along for a girl’s weekend.

We spent Sunday night for Memorial Day weekend in a queen sized room.

There was no view. We had a full load’s worth of towels from one night. And for once, we drank more water than alcohol.

This is my second staycation of my life. It’s a recent trend that I haven’t really explored because I love traveling.

But, there are so many parts of Chicago to explore that staying in a different part of town can seriously feel like you are in a different part of the world.

Transit to the Palmer House: Taxis v. Uber

My friend and I both live in the northside of Chicago. We could easily take the CTA redline downtown, but she said we should take an Uber. Uber’s were surge pricing, so we grabbed a taxi—big mistake.

This taxi driver was nice at first. He called us models and played Beyonce. But, then my friend got on the phone and the taxi driver asked me to take off my sunglasses so that he could see my eyes. I looked down and started playing Views. 

Shortly after his wife called and he put their conversation (in another language) on Bluetooth.

We finally got to the Palmer House, and I jumped out of the taxi. And taxi drivers wonder why we take Uber’s.

Which way to the Steam Room?

The Palmer House is gorgeous. It’s located right off State Street on Monroe.  It’s ornate and has so many passageways, stairways and oddly enough, not enough elevators. We check-in and immediately wanted to do what we came here to do – get a steam and go for a swim.

They have an entire spa on the fifth floor, but we opted for a steam and a few minutes in the Jacuzzi.

I recently joined LA Fitness and have become obsessed with their sauna, but it was nice to be in an actual steam room. It helps you calm down and breathe and not become overwhelmed by your environment.

Becuase the steam room literally makes you feels like you are suffocating.  I had to leave the room twice – but once I started focusing and breathing, I calmed down. If you are feeling stressed – go to the steam room.

It’s Just You and Me (and the rest of the world):

After the dew collected on our skin, it was time for the Jacuzzi.

We realized everyone and all of their children were in the pool. I literally felt like I was at a daycare. So we climbed up the stairs to the more secluded Jacuzzi.

We got in and started chatting. My friend showed me that a Jacuzzi is supposed to be a massage.

We sat back and let the bubbles massage us. I’ve seriously been Jacuzing wrong my whole life.

Steamimg_6319, Jacuzzi, Beautify:

After a little pampering, we decided to grab our third towel of the day and go back upstairs for some Kesha.

The best past of a girl’s weekend is getting ready. My friend loves hair and makeup, so she helped me contour my face. We used Fiona Stiles powder and purple mascara, and then a travel kit from Ulta with eyeshadow and blush.  And yes, it does take 45 minutes to get all dressed up.

 Nando’s Chicken:

My friend grew up in the UK so I surprised her and took her to Nando’s Chicken. Yes, it’s got a casual vibe, but the chicken is so good.

We ate chicken and talked about our work life. As two single girls, it was nice that girl’s weekend didn’t turn into a diatribe about men but more about talking about our goals and dreams and our next career steps – you know, productive things.





Dancing on Hubbard Street:

The best part of staying downtown is walking across the bridge and seeing the Chicago River and all of the beautiful buildings surrounding it at night. It’s sights like this where I am still amazed that I live in such a beautiful city.

We went to Hubbard Street – a spot in Chicago known for its night life. We started the night at Rockit Bar, where I met a girl who is 6’2″ sans heels. We had to take a picture.

We got back to the dance floor and security came beside us.

“What’s he doing?” I asked my friend.

“He’s escorting us.”

After the bar got too techno, we went to Mercer. Mercer always has good music – but not a lot of people. We formed a girl group and started getting low to Jay-Z with more UK girls.

We were going to meet up with a guy, and ended up at the Bottled Blonde, which is on Wells and Illinois. I’ve never been there, but it is pretty amazing.

The drinks are good, the music is on point, and there are people – lots and lots of people. We danced with an Indian visiting from Atlanta.

A guy came up to our table and complimented us for being the most diverse group in the club.

After a few throwbacks (hey, R. Kelly), we walked the mile back to our hotel and like a true girl, spent the rest of the night trying to get feeling back in my toes after five hours in four-inch heels.

Hollywood Theme:

The Palmer Hotel is Hollywood themed. It has pictures of movie star classics on the wall, and yes, you do feel like a movie star just walking into their lobby.

My friend saw a picture on the wall and she was intrigued. She went online immediately and looked up her name from the picture. It was Dorothy Dandridge.

Dorothy Dandridge is like Kerry Washington. She is stunning.

Dorothy Dandridge was part of the Dandridge sisters, but like Beyonce, she went solo and then was cast in a movie that made her a sensation. She was the first African-American to be nominated for an Academy Award for Best Actress for her role in Carmen Jones (an adaption of the opera, Carmen). Gace Kelly won the award, but she was still an overnight sensation.

She became over $100,000 in debt from bad management (p.s. never date your manager). She was going to make a club appearance when they found her dead at 42 in September 1965. It was reported that she didn’t even have $2 in her bank account.  A tragic life; a Hollywood life.

You can read more about her life here.

Amenities of Life:

We woke up the next morning and jumped on the bed. Yes, that’s what you should do. It makes you feel like a rockstar. My friend did a four-mile run and then we did a repeat of last nightimg_6383 – steam, Jacuzzi, beautify. We met a .mother and daughter from Minneapolis. Pro tip – Minneapolis is one of the most healthiest cities in America. I asked her how that is. She said it’s because all of the lakes are free and open to the public.

“And what do you do during winter?” I asked.

“Oh, I go to the gym,” she laughed

All a girl needs is a good steam, some Jacuzzi time, music and makeup, a dance floor, and some Burberry Touch mixed with Victoria Secret’s Heavenly, and some next door chicken from Nando’s, and some Matcha GreenTea Lemonade from Goddess and the Baker. Those are the true amenities of life.

We grabbed breakfast at Goddess and the Baker along with the rest of Chicago  – biscotti and hot chocolate ,please.

I came into this weekend feeling overwhelmed, and now I feel confident and refreshed and most importantly, relaxed.

It’s so nice to meet all of the beautiful and spirited people who live in Chicago and who visit. But, it’s also nice when you get the steam room to yourself and can walk home from the club.

Cheers to girl’s weekends.

For more ideas for girl’s weekends or just a weekend travel, subscribe to Windy City Cosmo here.






Amanda Elliott 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.


Plan a Girl’s Weekend Chicago Staycation in Rosemont

This is a sponsored post. 

Rosemont is Vegas.

There are no strip clubs (just strip malls) and there are no dance clubs.

You don’t go to Rosemont for the arts or the history. You go there to be entertained.

I took my first vacation for 2016 in Chicago. Part of being a city girl is having access to the international and national airport hubs, buses, and trains to go travel some place new. As much as I love Chicago, I also love that it gives me the chance to getaway.

I recently had the opportunity to experience Rosemont attractions and accommodations through a Rosemont Media Tour for a staycation. Though I have crashed with other people at Chicago hotels for conferences and other occasions, this was my first proper staycation.

The experience was quite perfect, and I want to share with you some highlights of the staycation for a Rosemont travel guide.

Transportation in Rosemont:

Getting to Rosemont is like traveling. You take the Blue Line north and west all the way to the Rosemont Blue Line CTA Stop. There were Pace buses (you can use your Ventra card) right at the Blue Line CTA Stop to drop me off right in front of my hotel, Loews Chicago O’Hare Hotel. My friend and I came right from work on Friday night for a girls’ weekend.

I had a moment to drop off my bags, and then a hotel shuttle took me right to MB Financial Park for a one-stop night of entertainment and of course, food and drinks.

Rosemont is walkable and offers free transportation to the main attractions. You don’t need a car because if the hotel shuttle isn’t taking you to your destination, there is a trolley, a bus, a train, or even your own feet can take you there. Everything really is that close.

You can be entertained longer in Rosemont. Most Chicago bars and clubs start closing down around 1:30 am. But in Rosemont, you will be entertained until 3:00 am—the time that most businesses close, including the candy store—when a complimentary trolley, the Entertainment Circular,  will take you back to your hotel.

There are many key sites in Rosemont for business and pleasure which include:

MB Financial Park for food and entertainment

The AllState Arena for music

Rosemont Theater for arts

The Donald E. Stephens Center for business conventions

The Fashion Outlets of Chicago for discounted shopping

Rosemont really is it’s own mini-city that is perfect for travelers from O’Hare International Airport to explore during a layover or for Chicagoans to have a weekend getaway because of the attractions and the transportation and nearby hotels and airport.

MB Financial Park: Non-Stop Entertainment

Rosemont is better than any block in Chicago for entertainment because the majority of the entertainment and restaurants is in one giant circle, MB Financial Park (5501 Park Place).  Within this 200,000 square feet circle, you have your choice of international cuisine, movies, live music, and comedy.

Don’t get me wrong, Chicago has some great neighborhoods to explore and world-class entertainment and accommodations, but sometimes you want a convenient bar crawl.

During the winter, the center turns into an ice skating rink for the first part of winter and then solely a hockey rink for the rest of winter. On the side is a mini snow slope for sledding.

Rosemont Restaurants:

What I love most about MB Financial Park is that there really is a different flavor and flare at each restaurant. While I was in Rosemont for a staycation, I was able to sample multiple restaurants. As a Floridian, I felt like I was visiting different countries like at Universal Studios because each restaurant expressed a different culture and at the very least, created an entirely different atmosphere—while at the same time being fun and exciting.

There were your calmer, more relaxing spots like the Muvico Theater and Park Tavern, but having a pub crawl is just too easy, especially with the trolley service at the end of the night.

Adobe Gila’s Margarita Fajita Cantina guarantees homemade guacamole and fresh margaritas. The entire restaurant is transformed into positive vibes and tropical theme despite Chicago winter’s stark contrast.


Fogo de Chao Rosemont dining room

Fogo de Chao Rosemont dining room. Photo Credit: Fogo de Chao


The best food in Rosemont was at Fago de Chao. Oh, my word, the jumbo shrimp was so fresh, and the meat was cooked to perfection. Fago de Chao offered Brazil’s national drink—yes, Brazil has a national drink—the Caipirinha, but their food was far superior. They offer a full salad bar, generous meat portions, and a classy, upscale environment for business meetings or a nice dinner out for a romantic staycation.

Live Entertainment with Dinner:

I really felt like I entered a different country when we ate at Hofbrauhaus Chicago, a German restaurant complete with live German singers and musicians, and authentic German beer served with soft pretzels alongside the standard cheese dips and mustards.

There was also live entertainment at Five Roses. Five Roses reminded me of Lady Gregory’s in Andersonville because we sat in the back in the library. We tried English fish and chips and paired it with Old Rasputin’s, a heavier drink. On a Friday night, they had a live singer and guitarist. He had a John Mayer vibe.


The library room at Five Roses Irish Pub in Rosemont.

The library room at Five Roses Irish Pub in Rosemont. Photo Credit: Five Roses


Candy and Drinks:

For drinks, I would actually go to the candy store. Don’t skip The Sugar Factory. They have a bouncer outside because  you are sure to leave with a sugar high or, at least, a bucket of candy. The Sugar Factory has too many types of sweets to offer from the sweet and sour to the chocolate dipped nuts and pretzels. We decided to grab our bucket of candy after laughing the night away at Zanies. Don’t miss the opportunity to take a photo behind The Sugar Factory banner.

Park Tavern is just that, a tavern. Their food is above average bar food, and their drinks can get super sweet. However, the favorite beverage of the night went to the Park Tavern for their cherry drink—The Irish Soda—with Cruzan black cherry rum, Jameson Irish whiskey, and Sprite.

Kings Bowl

Kings Bowl in Rosemont. Photo: Amanda Elliott

Another favorite drink was at King’s Bowling Alley. They have a fruity drink, Sour Patch Kings, with Sour Patch Kids candy inside. It’s an actual fish bowl and also has Tequila, Midori, Fresh Lime Juice, Orange & Apple Liqueurs, Blue Curacao, Sour Mix and Sour Patch Kids Candy with a Sugar Dipped Lemon. Bring friends to help you as you drink and bowl at King’s Bowling Alley.

For beer lovers, you can’t pass up, Hofbrauhaus, though. Their beer is really good. We tried the Dunkelgold, a malt flavored beer.


A Night in Rosemont:

We were offered to eat the world, but we decided to drink it instead.

One of the most anticipated activities of the night was indoor skydiving at iFly.


Indoor skydiving at iFly in Rosemont.

Indoor skydiving at iFly in Rosemont. Photo Credit: iFly

Be warned, iFly is a sober activity. I suggest starting with skydiving. And after that high, drinking your way into the night and ending with comedy at Zanies.

It can also be overwhelming to do everything Rosemont has to offer in one night. I think you need a good drinking and entertainment night in Rosemont and then a fun, active day of shopping and indoor skydiving.

After eating and drinking in Rosemont, we had the option to do indoor skydiving, bowl at King’s or laugh at Zanies standup comedy club.

Zanies Comedy Club:

We opted to laugh in Rosemont. Chicago has some great comedians, and I have been to Second City, Up Comedy Club, iO Theatre, and The Laugh Factory, but honestly, I haven’t laughed as hard as I did at Zanies.

Zanies Comedy Club in Rosemont. Photo Credit: Amanda Elliott

Zanies Comedy Club in Rosemont. Photo Credit: Amanda Elliott

Zanies is strategically set up on one-level so that everyone can see the comedian, Cyndi Nelson, the General Manager told us over Mango drinks. I greatly appreciated this because we were late to the 8:00 pm comedy show. Even though we were seated in a booth in the very back, I could still see the comedian the whole time. In standup, body language is just as important as the punchline.

The first comedian was funny. His best joke was about his height.

The headliner was James Davis, a writer, comedian, and reoccurring guest performer at the B.E.T. awards. Davis was amazing. Everyone agreed. He brought us back to Boy Scouts, to the days of high school, and then added in lines about being a closer on Christian Mingle dating to being that one black friend.

Davis called himself a California roll.

“If black people are sushi, I’m the California roll. Go to some other hood for wasabi.”

The best quote of the night was:

“Being in yout 30s is like being in the same party bus in your 20s, but being in it on your way home.”

Like most comedy clubs, there is a two drink minimum at Zanies. There is also a special dinner at a local restaurant and Zanies comedy club combo.

Staycation Accommodations:

After a really good night, we started phase two of girl’s weekend back at our hotel, Loews Chicago O’Hare Hotel, where we received fruit and Fiji and slipped into our comfy robes. All I need in life is a comfy robe, fruit, and Fiji.


My friend and I had a private tour of the hotel and saw the art gallery in the hotel with pieces priced at $70,000.00. We also toured the banquet halls, where we stood beneath gigantic rose-shaped light fixtures.

Art gallery at Loews Hotel in Rosemont.

The art gallery at Loews Hotel in Rosemont. Photo Credit: Amanda Elliott

We then met the Sous Chef, Scott Becker, at The Ashburn, the restaurant at the hotel which took its name from Chicago’s first airport.  Becker took us on a tour through the kitchen, where they were slicing what appeared to be dozens of apples for their homemade Whiskey Apple Cobbler. This new restaurant opened two months ago and includes unique features like sectioned off barn doors.

That night, we had a nightcap. The Ashburn has 13 beers on tap, though not Stella. We decided on cocktails and chatted with other guests on the media tour over popcorn, which I promise tasted like pickles.

Becker explained that he adds different garnishes to the popcorn.

We had a good stay at Loews Chicago O’Hare Hotel, but it is definitely set up for business clientele due to their conference space, huge lobby, and proximity to the airport. It was a great stay for a staycation, it was only missing a pool.

Our hotel room faced west,  but if you get a hotel room that faces east, you can wake up to a picturesque skyline view of Chicago.

Loews Rosemont hotel lobby.

Loews Rosemont hotel lobby. Photo Credit: Amanda Elliott

The next day we had brunch at The Ashburn. The smoothies on ice, the fresh orange juice and the fruit and yogurt parfaits were a perfect way to jumpstart a day of shopping.

The Fashion Outlets of Chicago:

A girl’s weekend staycation trip would not be complete without shopping. The Fashion Outlet of Chicago is huge and it is right next to Loews Chicago O’Hare Hotel.

The hotel shuttle dropped us off right in front. We met at the concierge service, where they took our coats and our bags, for a hassle-free shopping experience.

A guide pointed out new additions to the 130 shops including LuLu Lemon, which just opened this winter and now ships all of their sale items to this fashion outlet location.

We also learned about British fashion, with shops like L.K. Bennett, where Kate Middleton finds her infamously stylish shoes.

The Art of Shaving shop in Rosement

The Art of Shaving in Rosemont. Photo Credit: Amanda Elliott

My favorite shop was actually The Art of Shaving. Yes, it’s for men, but I was part of the demonstration and learned how to exfoliate, brush, and have a proper shave for men and women. My hand never felt so soft—and I have very soft skin. The cream that we apply protects our skin, but the key step that women miss is exfoliation, which you achieve through rubbing in the cream with a brush. The silvertip brush, which lasts almost a lifetime retails for $195 at the outlet location.

Michael Kors in Rosemont. Photo Credit: Fashion Outlets in Chicago

Michael Kors in Rosemont. Photo Credit: Fashion Outlets in Chicago

My friend and I went home with something from The Limited. I kind of love The Limited, Ann Taylor, and the Banana Republic. The Limited had better selection and pricing than the Banana Republic at this mall, though.

Overall Recommendation:

I am all for a weekend getaway with arts and entertainments and exploration, like my 48 hours in Charlotte, NC experience. But sometimes, it’s nice to stop planning and start relaxing and enjoying. That is what a Rosemont staycation can do for you—provide an entertaining vacation in one-stop without the lines and with all the perks.

A travel guide took us to almost all of the restaurants in the MB Financial park. She was amazing and informative. Alex Jakubiak from Carol Fox and Associates helped with the planning and logistics of the media tour and she was organized, responsive, and a key player in making my stay at Rosemont so enjoyable.

When you’re planning your Rosemont staycation, I would recommend at least one night in Rosemont. This will give you enough time to fully enjoy the nightlife and restaurants in the MB Financial Park at night, take advantage of the great hotels, and wake-up to indoor sky-diving and perhaps shopping the next day.

Where’s your favorite place to have a staycation in Chicago?