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First-time Chicago: a starter guide to the Windy City

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Take revolutionary architecture, award-winning cuisine, an outsized musical legacy and top-flight museums, and wrap them all up in an easy-to-navigate package. Now throw in a population of locals at once cosmopolitan and brimming with Midwestern good humor. That’s Chicago, a city that will roll out the welcome mat and keep you engaged whether you plan to stay a night or a month.

These local picks will guarantee a great first impression of the Second City.

view of towering Chicago skyscrapers from the Chicago RiverTake a river cruise for a stellar view of some of Chicago’s most stunning architecture © Andrey Bayda / Shutterstock

Get to know a few giants

The near-total annihilation of Chicago’s streetscape in the Great Fire of 1871 was a disaster with a happy ending: it left a blank slate upon which the country’s most visionary builders – like father of the skyscraper Louis Sullivan and Prairie School founder Frank Lloyd Wright – could conceive a modern, uniquely American architectural vernacular. The fruits of their labor continue to stand sentry around the Loop and beyond, mingling with masterworks from more recent innovators like Mies van der Rohe and Jeanne Gang.

One of the most efficient – and enjoyable – ways to orient yourself in both the city’s layout and its history is with an architectural tour. The engaging and knowledgeable docents of the Chicago Architecture Foundation put on the city’s best. The organization’s eternally popular river cruise is a good option for a general overview, while an assortment of walking tours offer deep dives into topics like Art Deco-era skyscrapers and Tiffany design embellishments.

young man walks along a neighborhood street past a colorful shop facade as the sun setsThe creative, bohemian vibe of Wicker Park is captured in its eclectic shops © Page Light Studios / Shutterstock

Hood hop while you shop

With its sprawling department stores, the Michigan Avenue retail district – first port of call for many visitors – may be magnificent, but you’re unlikely to rub elbows with the natives there. For a taste of the city as everyday Chicagoans experience it, you’ll have to make your way to the vibrant neighborhoods that radiate outward from the Loop. And there’s perhaps no better way to read an area’s aura than to browse its shops.

Heaven for hipster types, Wicker Park brims with gems like vinyl superstore Reckless Records and Gather, a self-described modern general store stocking ceramics and minimalist jewelry worthy of a Kinfolk spread. Queer-friendly Andersonville is the place to go for stylish vintage shopping with a side of quirk; pick up an old-school college pennant or a tartan throw for your preppy friend at Brimfield and score that taxidermy armadillo you never knew you needed at twisted Woolly Mammoth.

The vibe along Lincoln Park’s Armitage Avenue trends toward the tony. Stock up on locally made sweets spiked with unexpected ingredients like wasabi and coconut ash at posh chocolatier Vosges, and browse copper-stemmed champagne coupes and irreverent letterpress cards at Art Effect.

Book lovers should venture south to Hyde Park for a slow amble through warren-like 57th Street Books or, for the brainiest readers, 57th Street’s academically inclined sister store, the Seminary Co-Op.

Join the culture club

Mummies and T. Rex at the Field Museum, masterpieces by Georges Seurat and Georgia O’Keeffe at the Art Institute, flight simulators and model railroads at the Museum of Science and Industry: whatever floats your boat, Chicago’s got a world-class museum for you. For maximum enjoyment, bear in mind that an in-depth exploration of these signature cultural institutions demands half a day or longer; attempting more than one in a day is a surefire recipe for gallery fatigue.

For a quirkier cultural experience, drop into one of the niche museums and galleries sprinkled throughout the city. Music lovers, boogie on down to the South Side to probe the enduring legacy of legendary blues label Chess Records at Willie Dixon’s Blues Heaven and marvel at house music pioneer Frankie Knuckles’ vinyl collection at the Stony Island Arts Bank. With interactive exhibits on sports forensics, curses and the Cubs’ historic 2016 World Series win, the Chicago Sports Museum will score big with supporters of the city’s teams. In West Town, the Ukrainian Institute of Modern Art offers a window into Ukraine past and present via works from its citizens and diaspora.

top-shot of a hot dog served Chicago-style with peppers and cucumbers in a poppy seed bunJuicy Chicago hot dogs are famous for a reason © CKP1001 / Shutterstock

Dig into Chicago’s local dining delights

Whether you favor highbrow spots or budget-friendly ones, worldly flavors or all-American tastes, you’re in for a treat: Chicago’s dining game is one of the best in the US. The multicourse molecular gastronomy antics at Alinea, the madcap culinary lab of modern chef royalty Grant Achatz, are all the entertainment you’ll need of an evening, but if the price tag sends you into a cold sweat, head to the West Loop – the city’s “it” dining district – to sample a slightly-humbler version of Achatz’s fare (think fried chicken and cheddar rillettes) at Roister. Another West Loop notable, Paul Kahan, puts out refined Midwest-inspired plates at Blackbird, but if you’re not in the mood to linger over dinner, you can pop into Kahan’s butcher shop-meets-cafe Publican Quality Meats for a quick chicken parm or a restorative bowl of ribollita soup.

Chicago boasts flavors as diverse as its population. The local eminence grise of upscale Mexican cooking is Rick Bayless, whose Topolobampo offers an elegant take on pre-Columbian cuisine. Far less formal – but every bit as delicious – is La Chaparrita, a snug, cheerful corner store in the Little Village neighborhood that happens to griddle up some of the city’s best tacos. Pilsen’s HaiSous is a critical darling for its polished interpretations of Vietnamese classics, while the colossal bowls of soul-soothing pho ladled out along Argyle Street in Uptown make for one of the city’s most satisfying – and affordable – meals.

If post-meal naps rate highly on your travel to-do list, consider bunking up at one of the city’s many accommodation options with exciting in-house dining options. The lobby of the West Loop’s sleek, minimalist Ace Hotel is anchored by chef Jason Vincent’s City Mouse, where unpretentious but excellent fare – think service station-inspired breakfast sandwiches and fried caviar-cheddar “shooters” – sets a playful tone. In Logan Square, boho B&B Longman & Eagle offers a handful of rooms in which to sleep it off after indulging in the first-floor tavern’s hearty comfort dishes and lengthy whiskey list.

Don’t forget to save room for one of the city’s gut-busting culinary icons, like the umami bomb beef sandwich at frill-free Mr. Beef, pan pizza at Lincoln Park institution Pequod’s, and technicolor Chicago style hot dogs at local favorite Byron’s.

Drink up and get down

The city’s craft beer scene has hit the stratosphere in recent years, with new breweries popping up seemingly every week and even the most unassuming bars curating homegrown brew lists. Beloved local label Half Acre took its brand to the next level when it launched its sprawling Balmoral tap room and brewery in 2017. South Side beer geeks swoon over the selection at Bridgeport boozer Maria’s.

Cocktail aficionados will mix well in Logan Square, home to quirky takes on classic concoctions at Billy Sunday, tongue-in-cheek tiki libations at Lost Lake and whimsically named sippers at bar-meets-gallery the Whistler. Worlds apart in vibe but only 20 minutes away by cab, historically German Lincoln Square projects an easygoing Old World ambience; hit Huettenbar or Laschet’s Inn for comically large steins of weiss and altbier.

If you prefer to take your hooch with a side of entertainment, venues of all stripes abound. With its ultra-divey vibe and lineup of good-time DJs and catch-’em-before-they’re-famous indie bands, the come-one-come-all Hideout is the place to let your hair down and dance your socks off, while scruffy, long-running Rosa’s Lounge is a hype-free spot to soak up the best in Chicago blues.

bundled-up skaters brave the ice on the skating ribbon in Chicago on an overcast dayBelieve it or not, winter is one of the best times to get outdoors in Chicago © D Guest Smith / Shutterstock

Stop and smell the flowers

Perhaps the Windy City moniker is to blame, but Chicago’s outdoors appeal is seriously underrated. It’s possible to head out into the fresh air just about any day of the year here. Mild spring and fall weather is perfect for hopping on a Divvy bike and hitting the 18-mile lakefront trail or the 606, a disused railway line-turned-elevated park that links up trendy cafes and eateries (and some excellent day-drinking spots, if you’re feeling so bold). Summer brings beach season – and if sunbathing beside a lake seems strange, just consider the blissful lack of potential Jaws scenarios. Come winter, layer up and take a spin around the ice skating ribbon at Maggie Daley Park.

Practicalities

With eight lines that cut both overhead and underground paths across the city, the CTA train (or El, as it’s known by locals) is one of the quickest and most affordable ways to get around perpetually traffic-clogged Chicago; as a bonus, some lines offer breathtaking views. Most fares clock in at $2.50 (additional rides within two hours will cost you a quarter); the 45-minute Blue Line journey in from O’Hare Airport is $5. Buy your ticket – or a rechargeable Ventra card, if you anticipate multiple rides – at vending machines found in stations.

Admission to Chicago’s most popular museums and cultural attractions like the Shedd Aquarium, the Art Institute, and the Willis Tower Skydeck isn’t cheap; if you plan to visit more than two, shelling out for the Chicago CityPass – which includes admission to 7 major attractions, as well as perks like fast-track entry – can be a worthy investment.

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