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Home > Articles > Where to Go > City Break: Chicago
Where to Go 

City Break: Chicago

View from the John Hancock Center. Image: GettyView from the John Hancock Center, Chicago. Image: Getty

The last couple of hundred years has left the city in good-looking shape for the future. The addition of parks and public art sees the Windy City remain a visually welcoming place, with all the cultural, historic and gastronomic advantages you’d expect from a major city. The towering skyscrapers of The Loop are testament to the city’s economic muscle, and the patchwork of neighborhoods stretches far and wide. Lake Michigan figures strongly in Chicago’s character, giving it a lovely outdoor space in the summer but it means winters can be chilly. From world-class museums and cutting-edge restaurants to its renowned comedy scene, Chicago makes a good case for being the American Midwest capital.

Affordable views: Enjoy VIP views of The Loop without paying for an expensive tour. Buy a ticket for the L Train and get on the brown, pink or orange lines. Sit in the first car by the front-view window for the best panorama. transitchicago.com
Dog hungry: About an hour before you get hungry for lunch, take a cab to Avondale and join the line forming daily outside Hot Doug’s, where a hot dog genius serves up his creations to a discerning crowd. 3324 N California Avenue.
Laugh it up: Almost all comedy fans head to The Second City to see the theater where so many comedy icons came through the ranks. However, locals go to iO, the traditionalists’ choice for improvised comedy. secondcity.com

Must see
Cloud Gate:
If you’ve seen any of your friends’ photos of Chicago, they’d have been standing in front of Cloud Gate, the enormous metal ovoid better known as ‘The Bean’. It’s home is in the wonderful Millennium Park, boasting glorious open spaces, Frank Gehry-designed pavilions and the beautiful Crown Fountain.
Architecture tour: See the city’s history through its buildings by taking any tour offered by the Chicago Architecture Foundation. It runs downtown walking tours that show off beautiful late 19th and early 20th-century constructions, but an even better overview can be had from its glorious river cruise. architecture.org
Wrigley Field: Even if you aren’t a huge sports fan, the sheer amount of history on display at Wrigley Field — legendary home of the Chicago Cubs — is well worth a look. One of the country’s most historic ballparks, it was built in 1914 and still welcomes millions of fans a year. Tours are available daily. chicago.cubs.mlb.com

Image: Girl and the Goat

Image: Girl & the Goat

Where to eat
Girl & The Goat:
Where Top Chef winner Stephanie Izard works her magic with an array of livestock. girlandthegoat.com
Pequod’s Pizza: Head here for a perfectly caramelized crust on an otherwise very traditional Chicago deep-dish pizza. pequodspizza.com
BellyQ: The flagship restaurant of Asian cuisine master Bill Kim (and part-owned by Michael Jordan) features an amazing Korean menu. bellyqchicago.com

Where to sleep
The Langham: A grand feat of modernist architecture with fine art, palatial rooms and a luxurious spa. chicago.langhamhotels.com
Hyatt Regency Chicago: Recently reopened after a $170m revamp, it still features its famed cavernous lobby and now boasts more high-end dining options. chicagoregency.hyatt.com
Aloft Chicago: Slightly more affordable than the trendy W brand, but still with chic design and plush public spaces. aloftchicagocitycenter.com

Art Institute of Chicago: Located in Chicago’s Grant Park, the Art Institute rivals the Metropolitan Museum of Art in New York in size and breadth. If you only have an afternoon to spare, the highlight is definitely the Modern Wing, where you can see great works by Picasso, Matisse and Miro. artic.edu
Adler Planetarium: America’s oldest planetarium, its highlights are undoubtedly the two star-gazing theaters. But don’t miss its collection of historic astronomical equipment and keep in mind it also offers some of the best views of the city. adlerplanetarium.org
Symphony Center: Sitting in the Loop area, this music complex features a wealth of classical and modern music and dance performances, and three incredible halls in which to show them, including Orchestra Hal, a wonderful 2,500-seat auditorium that’s home to the Chicago Symphony Orchestra. cso.org

Art Institute of Chicago. Image: Corbis

Art Institute of Chicago. Image: Corbis

Winter Brew Festival:
This winter beer festival in late January gives revelers just enough time to recover from the New Year’s celebrations, and thousands of people head to Lincoln Square to partake. lincolnsquare.org
Chicago Restaurant Week: Starting in late January, this foodie celebration is a perfect opportunity to try some upscale establishments, with many offering special deals on fixed price menus. choosechicago.com
Theater Week: The city has a strong dramatic arts tradition, and to celebrate this, Theater Week runs for 10 days in mid-February, with 100 plays at lowered prices, so you can take in a nice variety. chicagotheatreweek.com

Where to shop
Ikram Goldman: The retailer shot to fame as the brand behind Michelle Obama’s flawless style but has been dressing Chicago’s well-heeled ladies for some time. Thanks to its First Lady patronage, the store in chic Millennium Mile has quadrupled in size. ikram.com
Wicker Park: If you don’t have thousands to drop on a single outfit, Wicker Park has affordable boutiques aplenty. Serving a younger, hipper crowd, stores such as Penelope’s show off up-and-coming designers. Look out also for independent bookstores such as Quimby’s, stocking the quirkiest of titles.
State Street: Home to Macy’s department store, a city landmark in its own right. As well as this icon of Chicago shopping, several popular no-frills stores have sprung up here, making it a haven for bargain hunters.
River North: The city’s main arts and gallery district, and long a fertile breeding ground for rising stars as well as established artists. This creative bent has spilled over into home design and interiors.


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