A Windy City Labor Day: My Luxe Weekend in Chicago

They call it the Windy City for a reason—and even in the midst of a summer heatwave, Chicago greeted us with breezy, sunny perfection. As someone used to Miami’s tropical humidity, the crisp air felt like a refreshing change. My first visit to Chicago left me utterly captivated, and after a beautiful Labor Day weekend, I’m already planning my return.

A Wedding Weekend in Chicago

We initially planned this trip to celebrate one of my best friend’s weddings (congrats to the newlyweds, Kati and Xander!), but it quickly became so much more than that. Since we’d never visited Chicago, and with the added bonus of Labor Day weekend, we decided to make the most of our time exploring this dynamic city.

Staying Downtown at the JW Marriott

Thanks to a savvy mix of Marriott Bonvoy points and American Express points, we split our stay between two neighborhoods to get a true taste of the city. Our first stop was the JW Marriott Chicago, nestled right in the heart of downtown. We were walking distance from iconic landmarks like Millennium Park (hello, Chicago Bean!), Chicago Theater, Grant Park, and more.

The timing couldn’t have been better—we stumbled upon the Chicago Jazz Festival in Millennium Park and enjoyed the smooth sounds of the city’s jazz scene, hosted by the Chicago Jazz Institute. Walking through the streets, I kept marveling at how familiar Chicago felt. So many of my favorite movies were filmed here, and I couldn’t help but think of it as a cleaner, more laid-back version of New York City.

Savoring Steakhouse Chic

You can’t visit Chicago without indulging in its legendary steakhouses. At the top of my list was Smith & Wollensky, where we feasted on dirty martinis, Caesar salad, and the most delicious steak tenderloin sandwich. Overlooking the river, we watched boats drift by in the perfect weather. The experience was just as I imagined—classic, chic, and oh-so-Chicago.

Exploring Chicago’s Local Hotspots

Of course, the wedding was the centerpiece of our trip, and our friends, being Chicago locals, took us to some must-visit spots like Enoteca Roma, Longman & Eagle, and the ever-funky Rainbow Club. The wedding itself was held at the stunning Cheney Mansion, a beautiful venue that perfectly suited the vibe of the weekend.

Gold Coast Glamour at The Viceroy Chicago

For the second half of our trip, we relocated to the Gold Coast neighborhood and checked into the luxurious Viceroy Chicago. With its rooftop restaurant, pool, and sweeping city views, it was the perfect place to unwind in style. The weather was absolutely dreamy—ideal for lounging by the pool with cocktails in hand.

The Gold Coast is known for its elegance and charm, and our stay here was truly magical. We had breakfast at Somerset, a chic spot located in the Viceroy. From there, we strolled through the picturesque streets of Oak Street before heading to the legendary Gibson’s Steakhouse for (you guessed it) more steak! The steak sandwiches were divine and washed down with Diet Cokes (no martinis this time).

A Culinary Delight at Le Colonial Chicago

The highlight of our dining experiences had to be our visit to Le Colonial, a gem in the Gold Coast serving French-Vietnamese cuisine. Every dish was a masterpiece, but my personal favorites were the Bo Luc Lac (shaking beef) and the Banh Cuon (chicken and mushroom ravioli). The meal ended on a high note with the Vanilla Peach Coconut Mille-Feuille and a refreshing Yuzu Mousse.

It was truly a dining experience to remember, and I was thrilled to learn that Le Colonial has a location in Florida too—definitely adding it to my must-visit list back home!

Chicago Is a City I Can’t Wait to Return To

As we wrapped up our weekend with a stroll around the Gold Coast, I couldn’t help but feel like this city had so much more to offer. From its rich architectural history to its world-class dining and entertainment, Chicago has firmly secured a spot on my list of favorite cities. Whether you're planning a trip for a special occasion or just looking to explore, I highly recommend making your way to the Windy City for a memorable experience.

Until next time, Chicago! ✨