A Relaxing Winter Weekend in Chicago

Living in southern Wisconsin, Chicago is just a short jaunt down the interstate and thus the perfect weekend getaway. Chicago offers endless opportunities for exploration, from its glittering skyline, myriad of museums, bustling neighborhoods, restaurants, and entertainment venues. I’ve been to Chicago dozens of times and have yet to see and do everything! In fact, I’m pretty sure I could spend the rest of my life there and still not get to it all.

I have vivid memories from childhood of driving into the city at night on my way to my dad’s house in Ohio. Inevitably, I would fall asleep shortly after getting on the road, but was always adamant that I be woken up before reaching Chicago so I could see the city. Driving into the city at night was magical then, and it remains magical still as an adult. It is one of my favorite city skylines of all time!

This weekend getaway was a Christmas gift from my husband with an emphasis on relaxation. Our first stop Friday evening was Casa Yari, a delightful Latin restaurant in Logan Square. We had tickets to an event at the Stan Mansion later in the evening, and this was the perfect place to dine beforehand. Street parking was easy and free on a Friday night and despite arriving at prime Friday evening dining time, there was no wait for a table.

We shared the Empanadas ‘a lo cubano’ for an appetizer – the mustard ailoi was divine – and the Dobladas for our main course. Both were excellent and we were super pleased with our choices. Important note – Casa Yari does not serve alcohol, but they do have a BYOB policy where you can bring your own alcoholic drink for a $2 fee per person. We enviously eyed the delightfully colorful shakes that other guests had ordered, but decided to save our sugar consumption budget for later in the weekend.

After dinner, we walked down the block to the Stan Mansion for a U2 Candelight Concert. The venue and the performance were both magical! The Stan Mansion was built in 1923 and was originally housed a chapter of the Knights Templar. It was fully renovated in 2018 and is now a stunning venue for weddings, concerts, and banquets.

After working all day, we were ready for bed after the concert, so we hopped in the van and drove 15 minutes downtown to the Hyatt Regency. As Hyatt Globalists, the Hyatt Regency is our favorite spot to stay when we’re in the city. When paying with points, Globalists receive free valet parking, free breakfast, free suite upgrades, and access to the Regency Club. These perks give us great value and make it affordable for us to travel frequently! Upon check-in, we were thrilled to learn that we’d been upgraded to a Skyline Suite.

Saturday morning we woke up early to enjoy our free Globalist breakfast at the American Craft Kitchen. This breakfast buffet never disappoints and features an omelet station and a Chicago favorite, Do-Rite Donuts.

Sufficiently stuffed, we hopped on the El to explore an area of Chicago we hadn’t explored before – Lincoln Park!

Because there’s never enough coffee, our first stop was Cafe Deko. Cafe Deko is a 1930s Art Deco inspired cofree shop and was packed on this late Saturday morning, and after ordering we waited about ten minutes to snag a table. It was worth it though, as the people-watching through the large windows was top-notch. We enjoyed a peppermint white mocha and a guava cheese croissant while planning out the rest of our day.

After enjoying our coffee and pastry, we walked down Diversey Parkway towards Lincoln Park, passing lots of adorable shops and restaurants along the way. Our next destination was the Lincoln Park Conservatory, a welcome warm retreat on this cold January day.

Admission to the Lincoln Park Conservatory is free, although timed entry tickets are required. Booking a reservation was easy and staff was on hand at the entrance to help guests with the process.

The conservatory was smaller than I’d expected and it only took us about 30 minutes to make our way through the four greenhouses. However, it was the perfect escape from the cold, dreary day and a great way to have some fun practicing my photography skills.

Next, we ventured back out into the lovely Chicago winter weather and headed towards the lakefront. We dreamed of returning in the summer to walk or bike the 18-mile Lakeshore Path that follows Lake Michigan along the city’s edge, but for today we enjoyed a dramatic winter landscape of ice and snow.

Even in the winter, the blues and greens of Lake Michigan are spectacular, especially against the moody sky and city skyline.

After spending some time by the lakefront, we were ready to warm up again, so we made our way back through Lincoln Park to another coffee shop we’d spied earlier in the day, Ludlow Charlingtons. Ludlow Charlingtons is a shelter dog-themed coffee shop featuring whimsical portraits of actual shelter dogs dressed in Victorian-era fashion. Although dogs are not able to dine in the cafe, during the warmer months there are bistro-style tables on the sidewalk where furry friends can join their owners for a coffee break. We enjoyed the Snickerdoodle Oatmilk Latte and a raisin danish, served in a dog bowl! The Snickerdoodle Latte was one of the best I’ve ever had, and I especially enjoyed our barista’s lovely latte art.

Sufficiently sugared, caffinated, and warmed, we wandered around the neighborhood for a while longer, enjoying some unique architecture along the way.

We made note of several places we’d like to return to in the future and stumbled upon the DePaul Art Museum. We enjoyed wandering through the exhibits before hopping back on the El train back to our hotel for a relaxing evening in. For dinner, we ordered Nancy’s Pizza and thoroughly enjoyed our thin crust pie while watching snow fall over the Chicago skyline from the warmth of our suite.

Sunday morning we slept in before spending most of the afternoon in the Regency Club planning some future travel. The Regency Club offers free drinks, snacks, and appetizers to its guests and is the perfect place to get some work done while travelling.

Before leaving the city, we had to have one last meal and ramen was calling our name! We enjoyed a late lunch at Kyuramen on Hubbart Street. This was such a treat! We tried the grapefruit aloe tea, steamed pork bao buns, and the MEGA Ramen bowl with Cashu Pork and Shrimp. All of the food was simply fabulous and we were delighted with the honeycomb booth we were seated in. This is a great location for a casual lunch or dinner with friends or a date.

And so our relaxing weekend in Chicago came to an end. We are already looking forward to spending another weekend there this summer, hopefully enjoying some warmer weather and chasing those blue skies.

Till next time,