Chicago Staycation at The Peninsula

In the weeks leading up to my birthday, I heavily debated ways to celebrate. It was important for us to adhere to Chicago’s current safety guidelines. So, I decided on a much-needed Chicago staycation. But what could be better than staying at the best hotel in Chicago?

The Peninsula Chicago Staycation Ideas

The Peninsula Chicago Staycation Ideas

So, I packed a bag for a true girl’s getaway at The Peninsula Chicago. Ranked the #1 Hotel in Chicago by Travel + Leisure’s World’s Best Awards in 2020. Staycations have always been a favorite way to relax and get away without the pressures of planning an out-of-town vacation. And as a single mom, it’s a comfort to know that you are just a quick drive from home

Chicago Staycation idea

“The Peninsula Chicago is the ideal destination for restorative comfort and the creation of precious memories. We invite you to enjoy a special time with friends and family, a long-overdue holiday, or a simple celebration of togetherness. Our “Sweet Home Chicago” package allows residents and regional guests to relax and rejuvenate in the city we call home.” -The Peninsula Chicago

Single Mom Travel

And — I’ll be honest — I’ve always wondered what life would be like living in downtown Chicago. So, Kiera, Bella, and I headed to Downtown Chicago for an extended weekend in the city. With the comfort of knowing that team at The Peninsula Chicago were taking all the precautions to guests safe.

Chicago Staycation at The Peninsula

Do single moms travel?
single mom travel with teen

What To Do in Chicago

Because Chicago is such a great city that I moved here twice! Now, it’s home.
I relocated to the suburbs just outside of Chicago in December of 2019. I had big plans to explore Summertime Chi. However, the 2020 pandemic shifted things. We have had to postpone our visits to the world-class museums, renowned tourist attractions, and the rooftop brunches that make the brutal winters worth it.

So, we have had the pleasure to safely support some of the delicious restaurants, admire the stunning architecture. And experience the kindness of our fellow Chicagoans from a distance.

video: The Peninsula

Our Staycation at the Best Hotel in Chicago

For our Chicago staycation, we decided to extend the weekend by checking in on Friday. One of the bonuses of booking the “Sweet Home Chicago” package was to secure an early check-in. Upon arrival, we were greeted by the valet and bell service team and guided upstairs to check-in. The grand hall leading to guest services is beautiful and offers views into The Lobby, with; its classic understated elegance provides ample sitting areas.

The Peninsula Chicago hotel

As the guest services team provided a brief overview of the hotel services and dining options; we knew it would be a fantastic weekend. Next, we were off to our upgraded suite, included in the Chicago staycation package. The process was seamless. The hotel staff provides such a warm experience that you almost forget that everyone is wearing a mask.

The Peninsula Chicago Executive Suite

Family friendly travel in downtown Chicago

The Peninsula Chicago offers a variety of rooms and suites, including connecting rooms. Great for being together with loved ones!

For our staycation, we were in the Premier Executive Suite located on the 8th floor. The spacious Premier Executive Suite occupies Michigan Avenue corner views of the hotel, offering picturesque city views from large windows.

The Peninsula Chicago Executive Suite
The Peninsula Chicago Executive Suite room

This suite provided ample room for my family to unwind and lounge. And there was even a built-in work area for me to connect to Wifi and wrap-up the workweek.

chicago staycation ideas


Because The Peninsula Chicago is where far eastern graciousness meets with midwestern hospitality. Through creating a five-star experience, you leave with #PENmoments that you will cherish forever. Here are just a few of my favorites.

Executive suite chicago peninsula #penmoments

If you follow me on Instagram, you know my love for my morning cup of Nespresso. The in-suite nutrition center features a Nespresso machine and specialty blends of teas. The elegant china made a simple moment feel that much more special.

luxurious marble bathroom

How could we not mention the luxurious marble bathroom, dual vanities, and this fantastic soaking tub? After a busy day, the perfect end was a soak in this oversized tub. And all while listening to acoustic music provided through the in-suite speakers’ system and mood lighting.

 luxurious marble bathroom in the peninsula executive suite during our Chicago Staycation

Dog-Friendly Traveling in Chicago

The Peninsula Chicago team takes dog-friendly traveling to a new level. We notified the hotel during the reservation that our dog would be traveling with us. So, when we arrived at the room, a dog bed, bowls, and water were waiting for Bella. They even offer a pet menu and walking services.

The peninsula chicago is pet friendly

Welcome to our Chicago Staycation on Magnificent Mile

Located just steps from Michigan Avenue, The Peninsula Chicago is situated on Magnificent Mile. Because Magnificent Mile is the heart of Chicago’s upscale shopping district, galleries, landmarks. such as the Water Tower, the John Hancock Observatory, the Pumping Station, and the Wrigley Building are all easily accessible.

The Peninsula Chicago Restaurant

Because The Peninsula Chicago is well-known for its on-site restaurants. From the contemporary- American menus at the Lobby. Including a chocolate bar, to the Z Bar & Lounge located above Chicago’s iconic Michigan Avenue. And voted the number one Chinese Restaurant in Chicago, Shanghai Terrace offers Cantonese delicacies with spectacular skyline views and cocktails.

But, we opted for in-room dining during our stay, which offered a white linin experience in our suite’s comfort.

The Peninsula Chicago Spa

The Peninsula Chicago Spa

Since our relocation from Florida to Chicago, the one thing we both miss is the pool. So, when Guest Services explained that we could reserve time to relax in The Peninsula’s indoor half-Olympic-sized swimming pool; we were thrilled! Floor-to-ceiling windows surround the pool with sweeping views over Chicago’s breathtaking skyline. It was so refreshing to peel off the layers and take a dip into the pleasantly heated pool.

So, our pool reservation was for noon on Friday, and there was one other guest in the pool area during our visit. Providing ample room for social distancing.

So I’m sure you can tell, our Chicago staycation at The Peninsula was nothing short of amazing! And a perfect way to celebrate my birthday. Needless to say, we are already planning our next visit for Afternoon Tea at The Peninsula.

Our Chicago Staycation at The Peninsula