It may be brawny and broad-shouldered, but for however no-nonsense it is, Chicago is much more than the sum of its parts. From its world-class dining and renowned architecture to its iconic skyline and boutique-lined thoroughfares, the City that Works has earned its place on the global stage. Check out our guide to make the most of a quick Windy City stay.
By Jennifer Olvera
Early Morning: Watch the Sunrise – Stroll the paths and catch the skyline awash in morning’s glow from breathtaking Northerly Island, a 91-acre man-made peninsula. Designed by famous architect and planner Daniel H. Burnham, it was the site of Chicago’s second World’s Fair, “A Century of Progress,” held from 1933-1934. chicagoparkdistrict.com
9AM: See Your Food at Valois Cafeteria – Lined with murals of fabled Chicago landmarks, this century-old Hyde Park eatery features visible steam tables and a direct view of cooks who turn out comfort food to snaking lines of post-church-goers and the Obama family alike. valoisrestaurant.com
10AM: Visit the Modern Wing – After an inspiring walk through Millennium Park — site of the stunning Jay Pritzker Pavilion, the verdant, five-acre Lurie Garden and noteworthy outdoor art exhibits, head to The Modern Wing at the Art Institute of Chicago. Designed by Pritzker Prize-winning architect Renzo Piano, its collection of 20th- and 21st-century art is a sight to behold. artic.edu
12PM: Score Smoke-Infused Seafood at Calumet Fisheries – Located on the 95th Street Bridge — the one the Blues Brothers jumped over in the John Landis film — this wood-scented throwback is a seatless, James Beard-awarded must, known for its smokehouse salmon, fried shrimp, trout and sturgeon, all sold by the pound. calumetfisheries.com
1PM: Rent a Divvy bike and hit Chicago’s Lakefront Trail – Traverse an 18-mile stretch of the Lake Michigan shoreline past harbours, nature sanctuaries, arcs of powdery sand and jam-packed boardwalks, while soaking up soaring skyscraper panoramas. divvybikes.com, choosechicago.com
3PM: Refuel at Garrett Popcorn – Among the city’s most beloved native foods is this popcorn shop’s Garrett Mix — a heavenly, salty-sweet blend of cheese corn and caramel corn, sure to will colour your fingers with lick-worthy flavour. garrettpopcorn.com
4PM: Hop on Chicago’s First Lady – Board a Chicago Architecture Foundation boat tour to view more than 50 of the city’s most legendary buildings, gaining insight from docents and taking in perspectives from the Chicago River. architecture.org [Photo: Adam Alexander Photography, courtesy of Chicago’s First Lady]
7PM: O.D. on Pork and Oysters at The Publican – When hunger pangs hit, make fast-tracks for Chef Paul Kahan’s boisterous beer hall, where house-made terrines, charcuterie, ultra-fresh bivalves and curated bevs are the order of the day. thepublicanrestaurant.com [Photo: Aysegul D. Sanford]
9PM: Bottoms Up The Aviary – An adjacent sibling to ticketed dining at Next, Grant Achatz’s ultra-sleek West Loop cocktail bar features high-concept drinks, served in special vessels with accompanying nibbles. For an even more intimate experience, book seats at speakeasy The Office below. theaviary.tocktix.com [Photo: Edsel Little/Flickr]
11PM: Get Your Sugar Fix at Margie’s Candies – This legendary confectionary — set within a triangular historic building in Logan Square — serves up hand-dipped sweets and massive sundaes in clam shell dishes, in tchotchke-laden, time-warp-esque surrounds. margiesfinecandies.com
12PM: Catch a Midnight Flick at the Music Box Theatre – Showing a roster of foreign and independent films beneath a ceiling of “twinkling stars”, this spot is reputedly haunted by “Whitey,” a former manager-turned-afterlife-protector. musicboxtheatre.com
2AM: Slumber in Style at Thompson Chicago – Awash in warm woods with mid-century designs, this 247-room Gold Coast Hotel has a bespoke feel and is within walking distance of Oak Street Beach and the shops-lined Magnificent Mile. thompsonhotels.com
9AM: Wake to Roasted Goat at Birrieria Zaragoza – No trip to Chicago is complete without a visit to Juan Zaragoza’s masterful Pilsen restaurant, a petite, family-run spot dishing up regional Mexican fare inspired by the owner’s childhood in Jalisco. Expect your birria tatemada to arrive with handmade corn tortillas, chopped onions, cilantro and fire-roasted salsa roja. birrieriazaragoza.com [Photo: stu_spivak/Flickr]
Watch Before You Go – The Blues Brothers is an iconic crime comedy starring “Joliet” Jake Blues (native Chicagoan John Belushi) and Elwood Blues (Dan Aykroyd). Beyond being a redemption tale about a paroled con, it features an endless array of Chicago locations, from Lower Wacker Drive to Maxwell Street and Daley Plaza. bluesbrothersofficialsite.com [Photo: Carlos Y./Flickr]
Read Before You Go – The Jungle, by Upton Sinclair, is a shocking 1906 exposé about the meat-packing industry, one that reveals the exploitative labour practices and unsanitary conditions endured by immigrant workers in the Chicago stockyards. amazon.com
Listen to Before You Go – My Kind of Town, popularised by Frank Sinatra, was originally part of the score for the 1964 Rat Pack musical Robin and the 7 Hoods. It was nominated for an Academy Award in 1964. youtube.com
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