Extended Layover in Chicago

When the Barbie pop-up restaurant opened in Chicago, it became the ideal excuse for a quick weekend trip. With a Saturday night reservation on the calendar, we planned a long weekend that balanced just the right amount of relaxation and excitement. From shopping and sightseeing to indulging in local food spots, this short trip proved that with the right planning, even a brief stay can be packed with memorable experiences.

Flying in Style and Staying in Comfort

I won't tell you to chase status with an airline, but if you can build miles and pay for trips, I say do it! That's exactly what I did for this trip, thanks Delta. For our stay, we chose the Renaissance Chicago Downtown, a centrally located hotel which we also used points for the booking. The combination of a convenient flight and a comfortable, well-situated hotel gave us the flexibility to focus on enjoying the city without worrying about the logistics.

A Day of Donuts, Shopping, and Sightseeing

Saturday morning began at Stan’s Donuts, a Chicago staple that lived up to the hype. We opted for the pistachio glazed donut, and it didn’t disappoint—it was the perfect balance of sweet and nutty, with a texture that was just right.

Our first stop was Millennium Park, where we of course had to take a picture in front (or behind?) the Bean. Even though it’s a popular tourist spot, there’s something captivating about the way it reflects the city’s skyline and the people milling around it.

With the Bean checked off the list, we shifted gears and headed into the Loop and West Loop for some shopping. The Loop offered a blend of big-name stores and more unique finds, while the West Loop was perfect for browsing through local boutiques. We enjoyed the contrast between the bustling energy of the Loop and the slightly more laid-back vibe of the West Loop.

Afternoon Vibes Along the Riverwalk

As the afternoon rolled in, we took a leisurely stroll along the Chicago Riverwalk, a picturesque pathway lined with bustling cafes and scenic views of the city’s stunning architecture. Tiny Tapp and City Winery provided the perfect spots to relax with a glass of wine and some light bites, watching the boats drift by and people enjoying the sunny day.

Before heading back to our hotel to get ready for the evening, we made a stop at RAISED, a rooftop bar offering panoramic views of the city skyline. With a cocktail in hand, we toasted to a perfect day and the anticipation of our Barbie-themed night ahead.

A Night in Barbie’s World

The highlight of our trip was the Barbie pop-up restaurant, a very fun experience. Stepping inside was like entering a life-sized Barbie Dreamhouse, complete with pink décor, glittering chandeliers, and playful, nostalgic touches. The menu was just as whimsical, featuring fun takes on classic dishes and cocktails with a Barbie twist. Every detail was on point, making it a night to remember.

From snapping photos in the Barbie box photo booth to enjoying the themed entertainment, the evening was a celebration of all things Barbie—fun, fabulous, and just a little bit over the top. It was the perfect way to spend a Saturday night in Chicago.

Night Cap

No trip to Chicago would be complete without a nightcap at Emerald Loop. This lively spot offered a laid-back atmosphere and the chance to unwind after an eventful day. With great company and a final toast to our incredible weekend, we couldn’t have asked for a better ending to our Chicago adventure.

Short Trips. Big Experiences.

This trip is a great example of how much you can fit into a short weekend with a bit of planning. Whether it’s a planned event like the Barbie pop-up or a spontaneous decision to explore a new city, you don’t need a lot of time to create lasting memories. Sometimes, a quick getaway is all you need.