Chicago: why you have to go to America's 'Second City' - what to do, where to eat, and where to stay

Elevated Train Tracks above the streets and between buildings at The Loop - Chicago, Illinois, USAElevated Train Tracks above the streets and between buildings at The Loop - Chicago, Illinois, USA
Elevated Train Tracks above the streets and between buildings at The Loop - Chicago, Illinois, USA | Rosana - stock.adobe.com

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From the easy, genuine charm of it's inhabitants, to the extraordinary culinary scene, brilliant bars to world class museums and art galleries - Chicago is my kind of town

“What brought you to Chicago,” the locals invariably asked me, in bars, arcades, thrift shops, restaurants, and yet more bars. After eleven days stalking the streets of Al Capone’s old stomping ground, Michelle Obama’s hood, Carmy’s culinary patch, I can say without hyperbole “because it’s one of the best cities in the world”.

You may bristle at that epithet, assuming a travel writer is given to over-hyping their destination. I will not quibble with you - scepticism is an attractive quality. But Chicago won me over with one outstanding attribute - friendliness. God, but the people are nice.

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Travelling on my own, I never wanted for company. I'd be offered Uber rides home from genial couples I chatted to over dinner, advice on where to dine from bar staff while being served. One raucous night I was folded into a group out for a celebration who utterly insisted I hang with them all evening. The Midwest's reputation for friendliness is not an exaggeration.

Good to know

Although the days of prohibition and speakeasies are in Chicago's past, they remain sticklers for I.D. If you want to head to any bars, make sure you keep it on you at all times

Where to go and what to see

 Carmen 'Carmy' Berzatto (Jeremy Allen White) walks under the 'L' tracks in FX's Chicago-set series, The Bear Carmen 'Carmy' Berzatto (Jeremy Allen White) walks under the 'L' tracks in FX's Chicago-set series, The Bear
Carmen 'Carmy' Berzatto (Jeremy Allen White) walks under the 'L' tracks in FX's Chicago-set series, The Bear | FX 2022

In the excellent Chicago-based series The Bear, two characters bemoan the gentrification of the Logan Square, Wicker Park and Lincoln Park areas of Chicago (although given the restaurant in the show operates out of the oh-so-upscale neighbourhood of River North, it’s somewhat hypocritical).

Colour me uncool (well, also, Very White), then - I loved my time walking these patches. Admittedly, I didn’t have a memory of what was lost. But into and out of dive bars, beer arcades (It’s an arcade! With booze! And free pinball!) boutique stores and cinemas, these neighbourhoods were pleasure palaces for arts, drinks and culture. Whatever your Chicago agenda, make the time to mooch around one - if not all - of these neighbourhoods.

Lakeview

Make a beeline for the Music Box Theatre (3733 N Southport Ave) - a single-theatre cinema that’s been operating since 1929, where they show classics and contemporary cinema alike. It’s a gorgeous art deco building just north of Lakeview. (If you adore the film High Fidelity you’ll recognise it at as the spot Rob Gordon and movie reviewer Penny go on a revival date).

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Jazz at the Green Mill - Al Capone's booth is at the front of the photo on the centre left. Jazz at the Green Mill - Al Capone's booth is at the front of the photo on the centre left.
Jazz at the Green Mill - Al Capone's booth is at the front of the photo on the centre left. | Katrina Conaglen 2022

A thirty minute walk, or five minute Uber north, it's worth popping into the Green Mill Lounge in Uptown, for an evening of jazz. During Prohibition it was owned by mobster "Machine Gun" Jack McGurn and Al Capone frequented it - you can still sit in his famous booth, said to be preferred because it allowed the mob lord clear views of all the entrances and exits. Drinks are appalling and it's a cash only venue. But the jamming was excellent, the vibe one of delipidated glamour - an absolute mandatory Chi-town historical experience.

Downtown Chicago

Chicago's downtown is known as 'The Loop' and is worth an afternoon's meander, to check out the fabulous steel-framed skyscrapers built at the end of the 19th century that make up the iconic skyline. Elevated trains chug over-head theatrically, while the skyward thrusting buildings inspire awe but don't overwhelm. No sarky New York attitude here: Chicago's downtown is as cinematic as Manhattan, but cleaner and friendlier.

The Loop does, however, drip with money, high-end shops, and the slight generic feel of a financial district. It doesn't need to take up too much of your time, but do make a bee-line for the 360 Chicago skyscraper (formerly John Hancock Centre). Whistle up the elevator to 1000 feet, where you can survey the city via 'Tilt'. This enclosed, glass and steel moveable platform 'tilts' you over the city, nothing but glass between you and a 1000 foot drop. It's exhilarating.

And it is worth a walk or run along the mile-long Riverwalk promenade. It offers a gorgeous vantage of the city and is lined with sweet café-bars if you need a pick-me-up.

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Take a drive to a temple

Bahá'í House of WorshipBahá'í House of Worship
Bahá'í House of Worship | Abodestock

If you have a rental car, it is worth the drive an hour's north of central Chicago to visit the Bahá'í House of Worship. The Persian prophet Bahá’u’lláh founded the Bahá’í Faith in the mid 1800s, and although there are 7 million practising members of the faith worldwide, there are only eight temples worldwide and only one in North America. It's one of the most breath-taking places of worship I've had the honour of visiting. With green gardens encircling a nine-sided structure covered by a single majestic dome, it has a distinct sense of calm and harmony to it. It's also free to walk around. To drive there from Chicago, take Lake Shore Drive north to Sheridan Road. The temple is located just off of Sheridan Rd. 

Five best ... films set in Chicago

Plenty of films are set in the windy city, but these ones stand out for capturing its essence (and actually were shot there)

  1. High Fidelity
  2. Risky Business
  3. The Untouchables
  4. Ferris Bueller's Day Off
  5. The Color of Money

Where to stay

Uptown ChicagoUptown Chicago
Uptown Chicago | 606 Vision - stock.adobe.com

There’s a rash of excellent hotels in the Magnificent Mile that will lend you easy access to various museums, the Chicago River Walk, Millennium Park, and the infamous ‘bean’ sculpture (actually known as the Cloud Gate - it’s pretty, worth a look) - a plethora of tick-box tourism pleasures. For ease, that would be an excellent place to stay, particularly if you have ambulatory difficulties. Personally, I found it a little soulless - and food and drink came at a premium price.

If you’re able to handle a brief commute (half an hour on the 'L' train in most cases, $1.25 per ride), I’d heartily recommend locating yourself either in Uptown, Pilsen, Southside or Lakeview. All are gorgeous neighbourhoods, full of character, great restaurants, interesting shopping arcades, lovely people, and easy access to the rest of the city via public transport. There are plenty of excellent airbnbs in the area, too.

To deep dish, or not to deep dish? Chicago cuisine

Deep dish, a Chicago cuisine staple, is surprisingly saucyDeep dish, a Chicago cuisine staple, is surprisingly saucy
Deep dish, a Chicago cuisine staple, is surprisingly saucy | Katrina Conaglen, 2022

Here is the skinny on deep dish: don't think of it as pizza. It is akin to a lasagne, only with a heavy bread crust. The one I sampled was, purportedly, average, so bon courage if you want to seek out something superior (Pequods, the locals say, is the best in the city, or a spot in Uptown called Milly's).

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It’s a curio, I think, rather than a genuine entity - but you have to try it*.

If you’re after a staple Chicago dish, you’d be better served by a Chicago Hot Dog (yellow mustard, green relish, chopped onions, tomato wedges, a kosher-style pickle spear, sport peppers, a dash of celery salt) - head to the Wieners Circle. Alongside the ideal Chicago dog, if you enjoy dinner theatre, you can hurl abuse at staff and be insulted back - it’s a whole thing. People seem to love it, but then it all depends on your mileage on being called a highly-sexualised moniker while awaiting fried food. For $20 you can order a milkshake and have the lady waitstaff jiggle their naked mammaries at you when they serve it. I resisted, somehow.

On the more rarefied end of things, I ate at Daisies, a pasta and vegetable joint in aforementioned gentrified Logan Square. The agnolotti was so good I found myself uttering sounds usually reserved for the boudoir.

Curried carrots at Giant, Logan Square - the type of dish that provokes spontaneous odesCurried carrots at Giant, Logan Square - the type of dish that provokes spontaneous odes
Curried carrots at Giant, Logan Square - the type of dish that provokes spontaneous odes | Katrina Conaglen

And the meal I had at Giant, another Logan Square spot, was unforgettable. Sharing plates with three strangers I met at the bar (told you they were friendly in Chicago) nary a bite that passed my lips - peppers with provolone and anchovies, ricotta and polenta caramelle with caramelized rapini, broccoli with smoked pepper dressing, caramel apple cobbler - was anything less than exceptional. All paired with superlative wine and, sat at the bar, I got to watch the chefs prepare my feast.

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There’s too many fabulous eateries in Chicago to even pretend to be comprehensive. A swift Yelp check is worth your while: people here really know their onions in terms of local recommendations, so there’s very little work involved in dining well.

Briefly, try Portillos for an Italian Beef - that's the amazing sandwich they cook en masse in The Bear, if you're a fan.

Then: Lao Peng You for dumplings, Scofflaw for gin and beignets (better than New Orleans, in my opinion), Gather for classic American cuisine, The Purple Pig for meat prepared every way you can imagine, Honky Tonk BBQ for pulled pork, and Nhu Lan Bakery for bánh mì. I'm grazing the surface, but all these spots had delectable offerings.

Where to drink

Spilt Milk, Logan SquareSpilt Milk, Logan Square
Spilt Milk, Logan Square | Katrina Conaglen

The terrific bars of Chicago run the gamut from high-end cocktail joints to delicious dive bars where a shot and a brew will set you back $6. I downed excellent whiskey and terrible beer while arguing about arthouse cinema in Delilah’s - for my money, probably the best bar in the world. If you're interested in whiskey it's a must - they have over 750 varietals.

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At the higher end of the spectrum is Spilt Milk, where I savoured delectable cocktails while singing along to 90s oldies (do you know all the lyrics to ‘One Headlight’? Turns out you probably do). Nine minutes south on the blue line of the L is an incredible hotel bar: for a slice of swank, hit the rooftop at the Robey. You can enjoy a sterling view of Chicago at night, while supping on cocktails such as the excellently named ‘Oaxacan on Broken Glass.’

Savouring the smoky mezcal in a 'Oaxacan on broken glass' at The RobeySavouring the smoky mezcal in a 'Oaxacan on broken glass' at The Robey
Savouring the smoky mezcal in a 'Oaxacan on broken glass' at The Robey | Savouring the smoky mezcal in a 'Oaxacan on broken glass' at The Robey

There is Chicago libation you'll likely encounter: malort. Talk to any Chicago local in a bar past a certain hour and if your smile is wide enough they’ll buy you a shot of malort. Warning: this stuff is nasty. That said, the credibility that comes with being able to deftly sink a shot of the grapefruit-derived liquor is worth the momentary displeasure (and the amplified hangover the next day).

Neighbourhood Watch - Pilsen

Street art in Pilsen is gorgeousStreet art in Pilsen is gorgeous
Street art in Pilsen is gorgeous | Getty images

I fell instantly in love with Pilsen, a neighbourhood that was originally founded by German and Irish, but then peopled by a large number of Czech immigrants who settled in the wake of the Great Chicago Fire of 1871 - hence Pilsen, named for Plzeň in the Czech Republic.

Nowadays, the streets of Pilsen are home to amazing Mexican restaurants, live music, cool vintage stores and a host of public artworks. It’s a fabulous place to locate yourself or just spend a day if time pressed - be sure to get an order of carnitas while you’re there (I heartily recommend Carnitas Uruapan).

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While you're there, head to the National Museum of Mexican Art - its free, and offers a unique insight into Mexican culture through folk art, photos and art prints.

Shopping in Pilsen is fabulous - for a fruitful rummage, head to Knee Deep Vintage, where retro clothes are artfully curated. And we spent a happy hour in Pilsen Community Books, browsing new and used books.

Non-stop connections to Chicago from the UK are available through courtesy of Norwegian (norwegian.com), British Airways (britishairways.com), Finnair (finnair.com) and Iberia (iberia.com).

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