Pimp My Weekend: Chicago
World-class food, whiskey, architecture, hotels and scenery... Chicago's the ultimate US long weekend break...
When you think of jetting off on a long weekend, the easy, most obvious choice is Europe.
The more adventurous may even dabble in the idea of a slightly more long-haul jaunt over to the east cost of America, but anywhere further has always felt it bleeds into the idea of a ‘proper’ holiday.
Well we’re here, rather jubilantly, to tell you not only can you easily visit America’s Midwest over a long weekend, but Chicago is the ideal place to visit.
The third biggest city in the United States (after New Yoik and LA), it’s a hub bustling with amazing food, art, music, hotels, scenery, architecture and so much more. All the best bits of a world-class city without any of the douchey attitude.
Here’s everything you need to experience in a three-four day visit to the Windy City…
Eat/drink your weight in deep dish pizza/whiskey
Chicago is famous for many, many things. But its most iconic, immediately stomach-rumbling Midwestern tradition is undoubtedly the Deep Dish pizza; with a crust taller than most small dogs, and gooey fillings piled way up to the top, it’s as much a gloriously ridiculous savoury dessert as it is a main course.
While there are countless places at which you can gorge your heart out, we recommend Lou Malnati’s Pizzeria - when three different locals namecheck the same pizza place, you take it seriously.
There’s far more to the city’s foodie scene than merely pizza, too. From hipster hotspots like Longman & Eagle, which offer a modern spin on the classic Chicago hangout, with world-class NOM (we had the Slow Roasted Cauliflower, Beluga Lentils, Caramelised Onion, Golden Raisins, Mango and Cucumber Raita, and we’re still dreaming about it), to The Chicago Diner, a veggie/vegan and meat-free spin on the classic American diner (we had an award-winning vegan Carrot Cake shake, and veggie BLT and sweet potato fries that were the epitome of hearty ‘cheat day’ realness), it's a place that repeatedly takes your culinary expectations and flips them sideways at every turn.
The city’s also got a burgeoning whiskey scene, led by Koval Distillery, Chicago's first booze-producing distillery since Prohibition. Established in 2008, they started out producing single-barrelled organic whiskeys, and their success meant they soon spread into liqueurs and speciality spirits. With their produce becoming increasingly popular around the world, get ahead of the curve and sample one of their throat-warming bourbons from its very birthplace.
Grab a beer and soak up the Blues
The Chicago blues are a form of blues entirely indigenous to the city, and lay claim to some of the greatest blues musicians of all time, including Muddy Waters, Jimmy Rogers, Bo Diddley, and Jimmy Reed.
The tradition lives on in a host of down and dirty blues dive bars around the city. Our pick’s Kingston Mines (the largest and oldest continuously operating blues club in the city). Grab a beer, perch up on a stool, and wile the whole night away watching some of the most entertaining, amusing and downright brilliant musicians you’ve ever seen.
Warning: you will want to buy a guitar/harmonica by the time you leave.
There’s rarely a week goes by when the city isn’t taken over by a food/music festival of one description or another.
From foodie heaven (Taste of Chicago) to music goals (take your pick from the Chicago Jazz Festival, Chicago Blues Festival, and Lollapalooza), you’re guaranteed an envy-inducing day out.
Then there’s the festival we rocked up to, Windy City Smokeout; a combination of the two - half country music, quarter BBQ meat-fest, quarter whiskey celebration, and 100% good time.
Chill out by the Great Lake
Perched on the edge of one of America’s great lakes, Chicago boasts an ocean-side vibe that’s instantly relaxing.
Whether you grab a bike, go for a wander along the shore, visit the fairground, or just grab a smoothie and collapse under the shade of a shore-lining tree with a book, it’s the epitome of soothing.
Gangsters and ghosts
Chicago has one of the US’ most fascinating histories - founded in 1830, it was doing great business until The Great Fire of 1871 destroyed one third of the city and left more than 100,000 homeless. Nationwide social upheavals around the turn of the 20th century brought many migrants to the city (which has its influence in the Blues legacy above).
The 1930s brought with it the arrival of gangster rule, including Al Capone and John Dillinger, who famously terrorised the city with an iron, murderous grip.
As the city continued to grow, it evolved in surprising new ways, whilst retaining the mystery and buzz of its heritage. Today you can visit the bars that Capone used to hang out in, and stay in hotels full of period touches, stuffed full of fascinating history.
We recommend The Blackstone Hotel, which not only glows with old-school wonder (check out its dazzling lobby), but has recently undergone a multi-million dollar renovation to ensure it’s decidedly on-trend.
With incredible views out across the lake, a fun and welcoming vibe (you can pick which US icon to have on your keycard - we went with Marilyn Monroe, obvs), great food in its Catalan-themed restaurant, secret rooms (you have to check out the Barbershop, which used to be Al Capone’s local), and its very own ghost (said to be the widow of Mr Blackstone himself), it’s the perfect blend of old and new.
Millennium Park is award-winning for countless reasons, boasting a heady mix of art, music, architecture and landscape design. From brilliant art and sculpture (Anish Kapoor’s hugely popular Cloud Gate - or ‘The Bean’, as most people call it, is Instagram goals), to an amazing amphitheatre space (on the morning we wandered round, the city was using the grassy area to host a Britney-blasting public workout), it’s a must-visit.
While we’re about to say two words that are unlikely to inspire rapturous glee - ‘architecture cruise’ - the Chicago Architecture Foundation River Cruise has been named one of the Top 10 tours in the US by TripAdvisor. It’s, frankly, the best way to soak up the kaleidoscopic variance in the city’s architecture.
A gentle cruise along the river (which boasts more bridges than any other city in the world, at 37), you’ll pass paddling kayakers, chocolate factories (the smell is delirious), and see the award-winning sights of the city, whilst getting an aural history lesson from the boat’s brilliant tour guides.
Get your baseball on
Even if you know absolutely nothing about baseball (hint: we don’t), you can’t miss a trip to Wrigley Field, the home of the Chicago Cubs.
As the current World Series Champions, baseball clubs don’t come much bigger - and whether you’re soaking up the game day atmosphere (in a nutshell, bonkers), or exploring backstage on a behind-the-scenes tour when the team aren’t playing, it’s a great introduction to one of the city’s proudest children.