A Neighborhood Spotlight: Chicago’s Loop

Kimpton Gray Hotel is a standout property in Chicago, housed in a beautifully restored 19th-century landmark in the city’s storied Financial District. While the area is steeped in architectural grandeur and home to some of the city’s most iconic buildings, it’s far from all business.

Bold architecture, rich history, and endless things to do — welcome to Chicago’s Loop. (Photo Credit: Nico Meier)

Make Kimpton Gray Hotel your home base in Chicago. (Photo Credit: @thegraychicago)

Step outside the hotel’s ornate lobby and you’ll find yourself surrounded by some of Chicago’s best hidden gems — from buzzy rooftop bars and gourmet coffee spots to cutting-edge art installations and stylish boutiques.

Whether you’re exploring nearby Millennium Park, catching a show in the Loop’s theatre district, or simply soaking in the city’s rich culture, The Gray puts you right at the center of it all.

The Perfect Chicago Wake-Up Call

First things first. When you’re hankering for coffee, get your fix at Dollop. A local institution with cafes all over the city, Dollop operates a sleek outpost under the L tracks on the southern edge of the Financial District.

Consider your wake-up call officially answered. (Photo Credit: @lisadieder)

The Windy City lives up to the hype — and then some. (Photo Credit: @caitfalcon)

Finely roasted Metropolis coffee is adjoined by a dizzying array of pastries from Dollop’s bakeshop and Beacon Donuts — you’ll have a hard time choosing between the chocolate glazed brioche donut or the coffee cake donut. (But why choose?)

While you’re there, hop across the street and fall down the literary rabbit hole that is the Harold Washington Library, the city’s main (and largest, by a long shot) library. With several floors of books to peruse, you could easily spend an entire day here. Be sure to ascend all nine stories to the top floor to relax in the winter garden atrium, a lush and sun-drenched room of zen.

The Loop’s Luxe Entertainment Hub

Rapidly cementing its status as one of the Loop’s premier destinations for shopping, dining, and entertainment, Block 37 continues to evolve.

Block 37 is the Loop’s premier destinations for shopping, dining, and entertainment. (Photo Credit: Marcus Loke)

This multi-level complex offers everything from global fashion brands to immersive experiences — including a luxe dine-in movie theater perched on the fourth floor, where you can sip cocktails while enjoying the latest summer blockbusters in plush comfort.

With its central location and ever-growing lineup of stores and experiences, Block 37 is where fashion-forward energy meets big-city buzz. And with casual eateries, grab-and-go spots, and sweet treats sprinkled throughout, it’s the perfect place to recharge, restock, or just escape the elements for a bit.

On Top of the Windy City

Maybe it’s because Chicago is the birthplace of the skyscraper — or maybe it’s our pancake-flat Midwestern terrain that makes vertical feats feel even more dramatic — but this city has a serious love affair with sky-high views.

The iconic Chicago skyline wouldn’t be complete without the Willis Tower. (Photo Credit: Pat Joseph)

Just a few blocks from the hotel, you’ll find the iconic Skydeck at Willis Tower (forever “Sears” in local hearts), perched on the 103rd floor of one of the world’s most recognizable buildings. The elevator ride alone is a thrill — your ears will likely pop as you rocket toward the clouds — but the real payoff is at the top.

The Skydeck’s crown jewel is The Ledge, a series of glass boxes that extend out from the building’s façade, offering a truly surreal experience for those brave enough to step out. You’ll feel like you’re floating, surrounded by jaw-dropping, unobstructed views that stretch into four states on a clear day. It’s a quintessential Chicago thrill and one of the most unforgettable moments you’ll have during your stay.

Vintage Vibes and Hidden Gems

One of the best aspects of the Financial District is its beautiful mix of old and new. While fresh and hot new shops are popping up all over the place, it’s always nice to hit up the historic destinations that made the area great in the first place.

Kimpton Gray Hotel is right in the heart of the Financial District. (Photo Credit: Allen Boguslavsky)

Historic sites include stores like Optimo Hats in the Monadnock Building, for hats that recall a bygone era of pomp and circumstance, and Central Camera, an olden photography shop filled with the type of camera equipment you’d expect to see in a black-and-white movie.

You’re also conveniently close to Jeweler’s Row, a strip of old-timey jewelry shops that runs along Wabash Avenue under the L tracks. Just head four blocks directly east of The Gray to find yourself in diamond heaven.

Cultural Classics and Holiday Charm

If opera holds a special place in your heart, then you’re staying in the right place. One of the foremost opera houses in the country, the Civic Opera House, is mere blocks west of The Gray. With several productions per season, there’s plenty to see and marvel at, or you can pay the building a visit and stare in awe at the striking architecture of this palace-like structure.

Don’t leave Chicago without experiencing a live show. (Photo Credit: Kainat Usmani)

A shining star of the holiday season around these parts is the beloved Christkindlmarket, which takes place Thanksgiving through Christmas in Daley Plaza, a couple blocks northeast of The Gray.

During this festive time, the plaza is transformed into a German wonderland of toys, cuckoo clocks, glassware, ornaments, scarves, accessories, and any other trinket you can imagine. Be sure and try some of the German Gluhwein, a warm mulled red wine served in commemorative boots that you get to take home.

Where to stay: Kimpton Gray Hotel