The ‘Windy City’, ‘The Second City’, and of course, affectionately, ‘Chi-town’ – Chicago is known by many names. But none of these titles can actually do justice to the irrepressible dynamism of this Midwest city; this constantly evolving city grew from a small 19th century trading town to become the busy, multi-cultural modern metropolis it is today (it earned itself the ‘second city’ moniker as the second largest city in the US, which title is now held by L.A however).
Ask anyone who knows the city well, and they’ll tell you: “I love Chicago”. Their reasons may be different, but it often comes down to the vibe, which, here is trendy but in an effortless kind of way; pacy yet laid-back; stylish but not showy. Whether it’s the vast Lake Michigan (‘City by the lake’ is another one of its nicknames) lapping at its edges; the stunning skyscraper architecture; the atmospheric dive bars where you’ll find some of the best jazz outside of New Orleans; or the buzzing food scene, you won’t run out of reasons to fall in love with Chicago.
Here are our top three:
An architecture river cruise:
While we usually steer well away from touristy tours, when my architect cousin recommended this, we had to. Chicago, with its futuristic skyline, has influenced American architecture over the years, and the city is a hotbed of design innovation. Downtown Chicago is a temple to modernity, probably as most of its buildings had to be rebuilt after the Great Fire of 1871 – and unlike many other such regenerations, rather than attempting to recreate what was there, it was built in a very future-facing manner – with many different styles, and quirky innovations on display.
A leisurely cruise along the Chicago river on an open-deck boat will offer insights into the history of the city’s development, little-known back stories for some of the more interesting buildings, views of everyday life taking place on the water and its shores, and photo-ops aplenty – including of the riveting movable bridges of the Chicago Loop (there’s one that permanently stuck in a half lift too!).
There are plenty of tours throughout the day, leaving from different points along the river. Alight at Navy Pier to tick this waterfront promenade off your list too.
The Art Institute of Chicago:
Forget the Met (OK, well, don’t really forget it!), but the Chicago Art Institute has been voted the Number One museum by Tripadvisor (not that we’re ones to go with user-generated review ratings, but take it from us, this one, they have got right!).
This, the second largest art museum in the US, has been housed in this location since 1893, after a slightly rocky inception prior to this, in a gorgeous Beaux-Arts building that was originally commissioned to host the World’s Columbian Exposition. Home to a humongous collection of art from around the world, including some of the finest collections of early 20th century European art, contemporary American art, and indigenous and African-American art, plus of course an impressive roster of exhibitions, it is the sort of place that one needs days to work through. Of the permanent collections, our favourite was the Thorne Miniature Rooms (and we’re not embarrassed to admit enjoying this more than a lot of the well-known masters!) – it’s a series of staggeringly intricate miniature recreations of historic European and American interiors in different styles, it really has to be seen to be believed! Even if you’re not an art lovers, it’s well worth a visit (just ask the museum-phobic husband!).
It's a good idea to invest in a Citypass, a well-curated ticket booklet (for all major cities across US) that offers discounted prices and in many cases, fast-track entry into major attractions; it goes a long way in helping save time by beating the queues.
One of the hottest tables in town without doubt is this, the first ‘casual’ venture from the Alinea team – yes, the one that is currently No. 21 on the World’s 50 Best list, and has consistently held three Michelin stars for several years. Answering the call from fans for something that is a bit less of a ‘dinner event’ than Alinea, and probably tapping into the global trend of relaxed, social dining, Roister oozes trendiness. Starting with the hip habit of having no name on the front door – (surely the tiny little feather logo is sign enough)!
Inside too, this Fulton Market – one of Chicago’s dining hotspot neighbourhoods – venue is of-the-moment, with a large communal table running through the middle of the room, and a truly ‘open’ kitchen where all the chefs’ action is front and centre. For those here to immerse themselves in the ultimate culinary interactivity however, it’s best to book a ticket (because that’s how it’s done here) for the exclusive downstairs ‘tasting table’ and leave the decision-making to the chefs. Upstairs, it is dark and moody, but still vibrant; a striking mural and popular tunes set a vibrant tone indicating that this is a place where you can let your hair down and have fun.
But the menu is very seriously conceived with none of the culinary artistry that Grant Achatz has developed such a renown for, compromised. It is compact and encourages sharing – and share you will want to, as every dish is envy-inducing, both from a presentation point of view, and taste.
There’s all sorts of international influences on the cooking – but quite a leaning towards Asian flavours – evidenced by the ‘pouch’ of eating equipment on the tables (this is table setting, 21st century style after all!) which includes chopsticks. These come in handy to tuck into the simply titled ‘beef broth’ – an exquisite, comforting dish of melt-in-the-mouth tongue and cheek (see what we did there?), udon noodles, and a perfectly soft boiled egg, luxuriating in a warm bath of umami broth. Also not to be missed is the Romaine stem salad with leaf puree, and ‘nduja vinaigrette (there’s that hint of the obscurity in ingredient selection again).
But Roister’s piece de resistance is its signature dish, the one that has won singular praise from everyone who has tried it – the whole chicken and chamomile (I dare not call it the fried chicken, as it’s so much more than that). A sharing dish – good for at least four people – this is essentially chicken in three (utterly delicious) ways. It is part roasted (but poached first so it is incredibly tender); part braised in a salad with chamomile dressing that will question any perceptions you might have had of a chicken salad before; and a beautiful crunchy fried chicken with a moreish sunchoke sauce – garnished with chamomile flowers for good measure – that you won’t forget in a hurry.
If you needed further proof of the immense inventiveness of the Roister culinary team, their triptych of desserts are it. Foie gras combines with chocolate, walnut, and marshmallows to make for a mind-bending, multi-layered dessert. And the deceptively titled ‘strawberries and milk’ is a smorgasbord of sweet and tart berries done in many different ways – from dehydrated to jam – perfectly set off by a crumbly shortbread base. They prove a fitting finale to a sensory journey of a meal.
Mind you, there’s plenty more to see and do in Chicago, and no doubt, an ever-changing repertoire too. As Mark Twain said, “”It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” Just consider this our personal hit-list of things that will (hopefully) stand the test of time.
And we’d love to know what you think of our recommendations or your personal experiences and tips for Chicago, so do comment here or come chat to us on social media!