48 hours in Chicago
The Illinois city packs a punch with artsy and attraction-packed neighbourhoods, stellar architecture and a food scene that goes well beyond deep dish pizza.
Anyone who decries Chicago as America’s ‘Second City’ must be putting ketchup on their hotdog – to reference a long-held local no-no – so festooned is the place with world-class attractions, from the gastronomic to the architectural.
Chicago’s unique character owes much to its Midwestern geography (mercurial climate included), with its proudly distinct neighbourhoods shaped by the mass immigration that powered its industrial machine in the 19th and 20th centuries. Ultimately, though, it’s a city shaped by water, dissected by the Chicago River and fronted by massive Lake Michigan.
While it’s arguably best visited in late spring or autumn, its hot, sticky summers sizzle with events such as the Chicago Blues Festival and Taste of Chicago. Meanwhile, those willing to brave the formidable winters can enjoy impressive festive celebrations, a spectacle matched only by March’s exuberant St Patrick’s Day.
Here’s how to get under the skin of this fascinating city over a weekend.
Courtesy of Choose Chicago
Friday
Check in at: The Robey. The beauty of visiting Chicago lies in exploring its neighbourhoods and this boutique Art Deco gem, which straddles hipster Bucktown and Wicker Park, is near much of the magic. Replete with fine features and designer decor, it’s a perfect introduction to the city’s grand architecture, and rooftop bar Up Room offers elevated cocktails.
Get your bearings at: Willis Tower, whose Skydeck features glass-box viewing ledges (pictured), or the former John Hancock building (now 875 North Michigan Avenue), home to 360 Chicago’s thrill ride TILT, which angles window-hugging visitors downward towards the city for epic views.
Courtesy of Choose Chicago
Continue your downtown discovery at street level, more than 1,000 feet (305m) below, clocking iconic structures such as the Wrigley Building while strolling Chicago Riverwalk. Window-shop along the Magnificent Mile, the city's main commercial hub, and make time for skyline-backed selfies at Millennium Park’s art installations – there's quirky video sculpture Crown Fountain and Anish Kapoor’s iconic Cloud Gate, affectionately dubbed ‘The Bean’ for its shape.
Hit the water: It’s an excellent way to appreciate the centre’s rich architectural tapestry, dubbed “a Grand Canyon of buildings” by the guide on my excellent Chicago River Boat Architecture Tour. The tour really helps unravel the environment, from historic Louis Sullivan standouts to modernist Mies van der Rohe marvels ($44/£36.50 for a 90-minute cruise; last sailing at 8pm).
Refuel at: Time Out Market, where a handy app lists all the outlets’ menus. Part of the foodie Fulton Market district, northwest of downtown, TOM shares the area with other tempting spots, such as tapas bar Boqueria and Girl & The Goat, serving contemporary small plates with global influences.
Karl Cushing
Catch a performance at: Lincoln Park’s Steppenwolf Company, over on N. Halsted Street. Founded in the 1970s, the theatre company's original ensemble cast included actor John Malkovich. Historic Loop area theatres such as the Chicago Theatre and Goodman are also worth considering.
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Saturday
Dose up on caffeine at: The Wormhole Coffee, on N. Milwaukee Avenue. Its one of Bucktown and Wicker Park’s many dependable coffee shops and its enticing morning menu vies for attention with its movie memorabilia-filled decor. Follow with a deeper dive into the local area, swinging by Margie’s Candies for ice cream and browsing stores such as Chicago Makers Pop Up Shop, before enjoying the elevated 606 recreational trail, a former rail route.
Antwon McMullen/Shutterstock
Grab lunch at: Chop Shop on N. Milwaukee, a food-focused events space where bottomless mimosas ease along the weekend Brunch and Beats offering, before spreading your wings to other northern neighbourhoods such as the Ukrainian Village and Polish Triangle. Highlights further north include Andersonville, a Swedish stronghold whose attractions include the cute Swedish-American Museum and excellent Lost Larson Bakery, and gay-friendly Northalsted, formerly called Boystown, where art-filled gay bar BIG CHICKS + Tweet is a personal favourite.
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Season willing, hit the beach at: Montrose and Fullerton, among the city’s finest sandy stretches. Alternatively, grab a Divvy bike and venture back towards downtown. The Lake Front Trail, snaking through the tree-lined parkland sandwiched between Lake Michigan and Lakeshore Drive, is one of Chicago’s finest pedals.
Enjoy upscale dining at: Oriole, on the Loop, revered for its high-end New American cuisine – or there are further tasting menu delectations on hand at Alinea. You could also book a table at masterful Mexican Frontera Grill, headed up by Chicago chef royalty, Rick Bayless – the spot has drawn crowds for decades.
Catch some live music at: Buddy Guy’s Legends, where Chicago’s world-renowned blues scene reaches its zenith, or head to a celebrated jazz joint such as Green Mill. Reportedly favoured by notorious mobster Al Capone, this cash-only N. Broadway Street venue offers live music nightly. Also check listings for venues such as The Salt Shed, new for summer 2022.
Top it all with a nightcap at: Billy Goat Tavern (pictured), whose storied walls papered with newspaper clippings and photos reflect its former life as a journalist hangout. Other local landmarks include Delilah's, where DJ sets soundtrack the cheap drink deals, and Three Dots and a Dash, with its playfully retro Tiki-style cocktail kitsch.
Karl Cushing
Sunday
Enjoy brunch at: Lula Café, in trendy Logan Square. Top picks at this Sunday standout include the brioche French toast and royale breakfast sandwich, featuring soft shell crab, gouda cheese and sorrel tartar sauce. Yum.
Get your culture fix at: The Art Institute of Chicago, featuring major exhibitions and a permanent collection that pitches greats from Van Gogh and Miró alongside famous American works including Edward Hopper’s Nighthawks. Home to Sue the Tyrannosaurus rex, the Field Museum of Natural History is another crowd-pleaser, especially if the weather wanes.
Photo Spirit/Shutterstock
Have late lunch at: Alice and Friends. Forsake Chicago’s infamous meatpacking past to sample this excellent vegan eatery, whose comforting combo of Asian and American classics spans everything from bao buns to Korean barbecue made with vegetable proteins.
Wander the Frank Lloyd Wright Trail: Ride the ‘L’ train out west to leafy Oak Park to enjoy this informative self-guided trail showcasing the celebrated US architect’s ‘prairie-style’ creations. Ernest Hemingway is another famous Oak Park former resident – the writer’s grand childhood home is now an interesting museum.
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Drive along Route 66: Sunday afternoon’s light traffic is also ideal for experiencing America’s much-mythologised Mother Road. Take a selfie by the Historic Route 66 Begin Sign on Adams Street before chalking up roadside highlights such as Old Joliet Prison, as featured in The Blues Brothers movie, and enjoy a memorable diner-style roadside meal at Lou Mitchell’s, or Dell Rhea’s Chicken Basket.
Get your giggle on at: north Chicago comedy club Zanies. A stone’s throw away lies The Second City, where acting and comedy legends such as Dan Aykroyd, John Belushi, Bill Murray and Tina Fey honed their quickfire improv skills.
Grab a nightcap at: a dependable North Wells Street waterhole such as The House of Glunz, or Green Door Tavern on nearby North Orleans St – both worth a visit for their characterful interiors alone. Alternatively, pootle back to The Robey’s Up Room to sip a tipple as you gaze admiringly out over that intoxicating skyline one last time.
Karl Cushing
For more information, visit choosechicago.com.
Lead image: Courtesy of Choose Chicago
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