An Architecturally Inspired Weekend in Chicago

by  Katie McElveen | Aug 28, 2019
Chicago, IL skyline
Chicago, IL skyline / lucky-photographer/iStock

Ravaged by fire in 1871, Chicago took a chance and decided to rebuild with style, inviting young architects to the Midwest and giving them plenty of creative space. It worked. Almost 150 years later, the city brims with structures so iconic that even non-architecture nerds will recognize some of them. 

Even better, all that creative energy didn’t stop at the front door — the interiors of the city’s hotels, restaurants, and museums are as much fun as the exteriors. Here’s how to enjoy them.

What To Do

A serious space upgrade in 2018 made the Chicago Architecture Center (CAC) more than just a place to pick up tickets for tours. Here, architects are elevated to rockstar status. The interactive Chicago City Model Experience (the world’s largest 3D-printed architectural model), utilizes touch screens so visitors can see just how large an area was devastated by the Great Chicago Fire by setting off simulated flames that  “burn” through the city. There are also scale models of the world’s most famous skyscrapers and a cool neighborhood guide that makes it easy to explore the 77 neighborhoods that comprise the city. Across the street, you can hop aboard Chicago’s First Lady for an architecture tour along the Chicago River led by CAC docents. It’s an engaging, low-stress experience: fun facts fly (like that the city reversed the flow of the Chicago River in 1900) and, since you’ll be looking up the whole time, there’s no bad seat in the house.

Like the National Gallery in Washington, DC, the Art Institute of Chicago combines both ancient, modern, and contemporary works in one massive but carefully delineated space. The original Beaux-Arts building was constructed in 1893 and celebrates Chicago’s architectural history with a collection of ornamental architectural fragments — carved limestone reliefs, ornate ironwork, decorative friezes, art glass windows — salvaged from local buildings. Open since 2009, the Institute’s Modern Wing was designed by Renzo Piano. Part of the design is Piano’s Nichols Bridgeway, an open-air walkway set 620 feet above the ground that connects the museum to Millennium Park. Access to the Bridgeway — which offers sweeping views of the Chicago skyline — is free.

For more adventurous contemporary art, head to the Museum of Contemporary Art Chicago, which is located within a 1996 building designed by Josef Paul Kleihues. Filled with natural light, the museum houses 2,500 provocative works from the 1920’s to the present. Don’t miss lunch or dinner at Marisol, the museum’s ground-level restaurant, where chef Jason Hammel transforms even the simplest of foods — toast, salad, roast chicken — into delicious flavor bombs that are both creative yet true to their roots.

Architect Frank Lloyd Wright will always be identified with Chicago. While working for the pioneering Chicago architecture firm of Adler & Sullivan, Wright built his first home in nearby Oak Park; more notable structures, including the 1893 Winslow Home and 1909 Unity Temple, are also located within Chicagoland. These days, though, the big news is Wright’s 1910 Robie House, which emerged in May from a multi-year, $11 million restoration. The home is filled with glorious Wright touches and innovations, including custom rugs decorated with a stylized outline of the house; 175 handmade art glass windows that Wright called “light screens;" and a ground-hugging silhouette built to echo the dimensions of the long, narrow lot. A three-bay garage housed the family’s collection of cars (Mrs. Robie was among the first women in Chicago to be issued a driver’s license) and a sunken, privacy-enhancing porch. The home’s original furniture, which Wright designed, is also on display. Wright personally fought two potential developers to keep the house from being torn down; today it’s a UNESCO World Heritage Site.

Where to Eat

Chicago has become a city of outdoor terraces; many operate even during the city's harsh winters, with views of blue sky and crackled ice mosaics. One is Cindy’s, which is helmed by Chef Christian Ragano and is located on the rooftop of the 1893 Chicago Athletic Association Hotel. The restaurant overlooks Millennium Park and Lake Michigan. Decidedly hip, the eatery's exposed steel beams, curving glass ceiling, and imposing brick columns give it the feel of a Great Lakes’ lighthouse. The menu here skews American, but is updated with world flavors like cilantro-based zhoug (a Middle Eastern staple) and raita, a cucumber-based Indian palate cooler. Another is Upstairs at the Gwen in the recently opened Gwen Hotel. The property is named for Chicago artist Gwen Lux whose sculptures decorate the McGraw-Hill Building, which houses the hotel. During the warmer months, the terrace welcomes both diners and drinkers; during the winter, patrons can make use of a small cabin fronted by an ice curling court.

Rather stay inside? Oversized rounded windows and an open floor plan keep Pacific Standard Time light and bright. Curved leather banquettes, pale wood furnishings, and lots of hanging plants evoke a cool California beach house. The restaurant’s design is so distinctive that it was recently awarded the top design prize in Chicago’s prestigious Jean Banchet Awards. Food, most of it emerging smoky and crisp from one of two wood-fired ovens, includes pizza and pita as well as roasted proteins like black cod, strip steak, and pork ribs. It’s hard to figure out what to order at Beatnik, West Town’s hip counter-culture landmark — not because the menu is huge (even though it sort of is), but because you can’t stop staring at the décor. Here, you'll find  a glorious jumble of oversized crystal chandeliers salvaged from a Los Angeles ballroom, a 40-foot-long carved Balinese panel, a Parisian bar, vintage streetlights, mountains of throw pillows, and painted silk umbrellas. Once you do order, the dishes (think spreads, well-spiced Mediterranean small plates, and delicious desserts) are delivered as they're prepared, which gives you plenty of time to gawk at the scene as you nibble.

Where to Stay

When it was constructed in 1893, the Chicago Athletic Association’s headquarters building was an architectural marvel. Fronted by a 250-foot tall Venetian Gothic facade inspired by the Doge’s Palace in Venice, the club was filled with ornately carved wooden accents, leaded glass windows, colossal fireplaces, Turkish baths, ornate mosaic floors, and a pool. After nearly being demolished, the dilapidated building was instead renovated and transformed into the 241-room Chicago Athletic Association Hotel in 2015. More than 1,000 artisans contributed to the restoration, which included salvaging painted floors from the fencing court and using them to line the elevator walls, recreating vintage plaster patterns, and rebuilding a basketball court. Rooms have athletic-inspired details like tape-wrapped legs and pommel horse benches; some have original leaded-glass details. Besides Cindy’s, restaurants include the Cherry Circle Room, which serves a menu loosely based on some of the club’s old menus in what was the men’s lounge and the Milk Room, a speakeasy that no one knew existed until they tore down a wall and discovered the tiny hideaway. 

From designing Chicago’s first skyscraper — the 1882 Montauk Building, which no longer exists — to sketching out the plan for Chicago’s city plan and lakefront, Daniel Burnham is on of Chicago’s most revered architects. His last commission was the city’s neoclassic Continental and Commercial National Bank Building, which was completed in 1914. Today, that building houses the 610-room JW Marriott. A few original architectural details remain, notably the façade and the elegant 6,000 square foot Burnham Ballroom, with its striking curved ceiling. The hotel gym is one of the largest in the area and has a vast menu of classes taught by Nike-trained professionals.

Find The Best Cruises
Find a cruise

Find the best deals!

Click on multiple sites to get the lowest prices

Click on multiple sites to get the lowest prices