Idealist City Guide: CHICAGO

The birthplace of the skyscraper, and home to a spectacular collection of landscape design and art, Chicago has plenty to hear, see, buy and taste. It’s the home of the Blues, the birthplace of house music and a lively jazz destination for longer than anyone can remember. Chicago’s reputation as a vibrant city is well known far and wide.

Speaking of which, you must give the city’s speciality try—deep dish pizza. Far from the original Italian version and much better than the imitation Deep Pan found in the UK. It has a buttery crust up to three inches tall and is dripping with cheese, toppings and sauce. Not for anyone on a low-carb, low-fat diet!

For those setting their sights a little higher than the dining table, the Beaux Arts architecture could make an aesthete out of anyone. The music heritage is smashing. In tech job growth, it gives Silicon Valley a run for its money. It’s the ultimate theatre town, and there’s a unique neighbourhood for everyone. Welcome to Chicago, where it’s so unbearably cold in the winter that it drives locals and visitors into the jewellery box-like insides of its stunningly designed buildings. Where the local ‘lake’ (Lake Michigan) is so long, you would swear you were looking out to sea from the heights of the Hancock Center.

If you get the chance, a trip to the Center’s 95th floor restaurant is worth the trip. Likewise, the Observatory (360 Chicago), has a 360° view of the city, up to four states, and a distance of over 80 miles. If you’ve ever wanted to swim high above the ground, the 44th-floor sky lobby also features America’s highest indoor swimming pool.

Shop here

Of course, Chicago has all the high-end department stores and chains you would expect from the 3rd largest city in the USA. The Magnificent Mile is home to Barneys, Tiffany, Saks, Cartier, Versace and all the high end luxury looks you can think of.  But here at The Idealist we like to pick out something a little different. What follows is a handpicked guide to some distinctive stores that we love.

Norcross and Scott

Chicagoans aren’t afraid of strong, bold lines in their furniture and interiors. That’s why they shop at Norcross and Scott Home (1476 W Berwyn Ave) who carry a variety of items, from Tom Dixon’s edgy brass candleholders to Shino Takeda’s colourful ceramics.


Named after antiques fiend and shop owner Julie Fernstrom’s favorite plaid, Brimfield (5219 N Clark St) skews English cottage-chic with midwestern United States swagger. Shop antiques, curios, and a highly curated selection of reclaimed furniture and vintage signage. Found a piece that needs upholstering before being shipped home? Brimfield is the place.


On the other hand, the purist or minimalist will probably prefer the wares at Gather Home + Lifestyle (2321 W North Ave) where most of the store is black, white, wood or leather.

Jayson Home

The buyers at Jayson Home (1885 N Clybourn Ave) must have some serious wanderlust keeping the showroom flush with fresh items of modern and vintage furniture, lighting, pillows, textiles, and tableware. They also have a floral department, and an annual fall flea market.


High-end home goods that make you want to live your best life are what fill the shelves at Elements (741 N Wells St), where you can find a mix of sophisticated items, like Christofle dinnerware and flatwear.


Right in the dining district is where you’ll find Rider (1115 W Lake St), a showroom of vintage furniture, apothecary items, a well-edited selection of women’s accessories thrown in there, all inspired by the idea of world travels. Sip on bespoke java at the in-store coffee bar or try their organic cotton candy (candy floss to you Brits!), and small-batch chocolate.

Sleep here

  • The Thompson (550 Wellington St W) offers a feast for the eyes that is equal parts classic, modern, luxe and comfort. Plus, guests can enjoy 400-thread linens, rain showers, and minibar snacks created by Dean & Deluca.
  • PUBLIC Chicago (1301 N State S) is branded as the “anti-boutique boutique, an anti-design design hotel”. So, if you’re looking for class, quirk, and a good place to fly a little under the radar then lay your tired head here.
  • Cambria Chicago Magnificent Mile (166 E Superior St) is midwestern charm and hospitality in a cleverly well-appointed space. It’s bordering on uber-chic hostel actually, except that everyone thankfully gets their own room, bathroom, and privacy. When you want to shed that privacy, head to the always-popular rooftop patio for a cocktail.

Discover Chicago art and design

Art lovers have the Art Institute of Chicago (111 S Michigan Ave), home to over 54,000 works including architecture and design, prints and drawings and pieces from around the world.

The Chicago Architectural Club which celebrates architecture through a free lecture series where you can come face-to-face in intimate conversation with some of the biggest names in building and architecture.

A slice of Chicago deep dish pizza

Eat well

Blue-collar Chicago started with a mid-western American palate for beer, meat and deep-dish pizza but has since grown undeniably sophisticated in its thirst for craft beers and superb cuisine. Like GT Fish & Oyster (531 N Wells St) where Michelin-starred chef Giuseppe Tentori uses menu items like lobster rolls and bivalves to challenge everything anyone ever thought about American seafood.

Boka (1729 N Halsted St) is romantic enough for a date night and inventive enough to delight even the most world-wearied palates. Try to get a seat near the giant living wall for a breathtaking view. Close to Boka (and also owned by the same group) is Balena (1633 N Halsted St), which serves modern Italian hearth-fired pizzas and a killer brunch.

At Milt’s Barbeque for the Perplexed (3411 N Broadway S), you can listen to thought-provoking speakers talk about life, politics, and do good in the world just by ordering more. The barbeque is kosher, the meats are smoked on-site, and 100% of the profits go to local community causes.

More sites

Chicago is jam-packed with Goliath-sized must-see sites, like Cloud Gate in Millennium Park, as well as some smaller, more hidden gems. If you’re apprehensive about missing something important, plan your visit to tie in with October’s Open House Chicago, which makes over 150 of Chicago’s design marvels more accessible to the public than they usually are. Sights like the stage of Frank Gehry’s Jay Pritzker Pavillion suddenly become public space for a day.

The Music Box Theater (3733 N Southport Ave) is a relic of a movie house, built in 1929, at a pre-Great Depression price of $110,000. Designed by local architect, Louis I. Simon, and erected by The Southport Avenue Businessmen’s Association, it wasn’t the biggest theatre in Chicago, but it is known for screening exclusively classic, cult and independent films. It still hosts over 200 events per years. And if you’re looking for more sumptuous theatres, don’t miss the New Regal Theater (1645 E 79th St), inspired by a Persian incense burner.

Lincoln Park Zoo (2001 N Clark St) is one of the most historically-rich in the country, and at only 35 acres, it’s easy to get through all of the attractions. That includes the Wild Things gift shop, dining at the acclaimed The Patio at Café Brauer, and the patterned latticework dome created by the visionary local architect, Jeanne Gang.

Getting there

Getting to Chicago from the UK is easier than ever, with some airlines flying directly to O’Hare Airport—a quick train ride from Downtown Chi-town. Virgin Atlantic tickets can cost about £680 from London to Chicago and back. British Airways advertises round trip flights for as little as £488 during March and as much as £803 on busy dates.

Image Courtesy Downtown (c) f11photo, Pizza (c) lenyvavsha / 123RF Stock Photo

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