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Chicago Beauties: 5 Iconic Buildings You Don’t Want to Miss!


I’ve been dying to go to places downtown during this time so wanted to feel closer to it by sharing some awesome places! This blog post is in collaboration with Flats and they helped explain each of the places way better than I could! If you are looking to immerse yourself in art and culture, then Chicago is the place to go. The streets are lined with galleries, theatres, and restaurants and that makes it a go-to for everyone from creatives to foodies. No matter what you seek in The Windy City, no exploration would be complete without a few stops at the iconic buildings that helped shape this historic metropolitan!

From old factories given a contemporary spin using adaptive reuse architecture to iconic historical sites overflowing with vintage charm, there are endless places to catch a glimpse of Chicago’s artful past. Below are 5 of my favorites!

The Lawrence House

Photo Courtesy of Flats

This former luxury hotel built in 1928 skillfully blends old Chicago’s beauty with contemporary living. Recently renovated into a modern Uptown apartment building, it has preserved key architectural details while offering residents a slew of luxe amenities such as a rooftop lounge and pool, a 7,000 square foot gym, and a grand lobby that is open to the public (pictured).

The lobby is arguably the real star of this historical marvel with its stunning details and amenities like a health food shop, bar, and cafe. You will be able to enjoy the beverage of your choice in one of the many seating options such as club chairs, the expansive leather sectional, or a lengthy coworking table. But no matter what seat in the house you choose, you will get a premium view of the lobby’s stunning vintage features such as the arched Art Deco skylights, terrazzo flooring, and old photos that are artfully displayed throughout. It is an absolute must-see that offers the perfect escape from the buzz of the city!

1020 W. Lawrence Avenue

Green Mill Cocktail Lounge

Photo Courtesy of Green Mill

The Green Mill in Uptown may have been designed after the famous Moulin Rouge in Paris, also known as the Red Mill. But since it was established in 1907, it has become an icon in its own right.

Enter the door under the green marquee sign that reads “Green Mill Cocktail Lounge” and you will be transported back to the mid-1900s. Locals and visitors of all ages come to mingle at this vintage-style jazz club that offers live music and poetry readings. It is complete with wood-paneled walls that feature scrolling frames, ambient lighting, and cozy booths—including the one favorited by Al Capone back in the day. You can also find a hatch behind that long end of the bar that Capone and his associates used to dodge authorities.

Nowadays, you won’t see people popping in and out of the underground tunnel that runs to the street. But you can still find great drinks, an energetic atmosphere, and live jazz music.

4802 N. Broadway Avenue

Chicago Cultural Center

Photo courtesy of Lyric Kinard

This designated Chicago Landmark building is a highly-sought out tourist destination in not just The Loop neighborhood, but all of Chicago. And for good reason. Designed as the city’s central library in 1892 and completed in 1897, this hotspot was infused with awe-worthy architectural elements. This includes a pair of glass dome skylights, lavish marble detailing, and eye-catching mosaics—all of which can still be enjoyed today thanks to this building’s preservation efforts and renewed purpose as a cultural center.

Beyond its exquisite details, the Chicago Cultural Center now presents more than 1,000 programs and exhibits annually that cover a wide variety of art. It is considered one of the most comprehensive arts showcases in the United States.

77 E. Randolph Street

Chicago Water Tower

Photo Courtesy of Charlottees

One of the few structures to survive the Great Chicago Fire in 1871, The Water Tower is not only an icon but a symbol of hope. Its limestone detailing and captivating silhouette makes this glorious piece of architecture a showpiece on Michigan Avenue’s Magnificent Mile. Being built over 150 years ago in 1869, it is listed on the National Register of Historic Places and ranks as the second oldest water tower in US history.

While you won’t find this tower pumping water anymore, it is now home to the Chicago Office of Tourism. This includes a free art gallery that is open to the public that features the talents of local photographers, artists, and filmmakers.

835 N. Michigan Avenue

Frederick C. Robie House

Photo Courtesy of David Arpi

Designed by Frank Lloyd Wright in 1909, this iconic house displays both the organic architecture and Prairie House style that helped propel Wright to fame. Some of its noteworthy features are the earth-toned color palette, abstract art glass windows, and heavy use of horizontal lines. These highlights allow it to not only blend into its surroundings (Organic Architecture) but also make it reminiscent of a Prairie landscape (Prairie Style).

This home was added to the National Register of Historic Places list in 1966.

Tours of the Robie House are available and highly recommended for any art or design lovers!

5757 S. Woodlawn Avenue

This list only scrapes the surface of what Chicago has to offer for icons. Other places of immense interest include The Wrigley Building, James M. Nederlander Theatre, Graceland Cemetery, Civic Opera House, Merchandise Mart, and Humboldt Park Field House (to name a few).

The beauty of Chicago is that you don’t have far to look to find the history and icons that helped build one of America’s most exciting cities!


Thanks to Flats for sponsoring this blog post.

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