Sunday 18 August 2019

Chicago: 19 things to do, see and eat in America's most under-rated city

Rugby Weekend 2016

Chicago's Magnificent Mile
Chicago's Magnificent Mile
Architecture tour of Chicago
Art Institute of Chicago
Margarita at Big Star, Wicker Park.
Chicago theatre
The 'L', Chicago
Soldier Field, Chicago
The Bean, Chicago
Pól Ó Conghaile

Pól Ó Conghaile

With Ireland set to play the All Blacks in Chicago this November, we've put together a bumper travel guide.

What's the story?

Ireland play New Zealand at Soldier Field on November 5 (kick off is 3pm local; 9pm Irish). Soldier Field is the home of the Chicago Bears, but Joe Schmidt and co will be determined to escape a mauling in front of 61,500 fans.

The match is part of the imaginatively-titled 'The Rugby Weekend', which also sees the USA Eagles take on the Maori All Blacks on Friday, November 4 at Toyota Park. Tickets are thin on the ground, having sold incredibly well already.

Erm... pubs?

Phyllis's, Ukranian Village, 1240.JPG
Phyllis's Musical Inn, Ukrainian Village, Chicago

Chicago is your oyster, travelling rugby fan. From craft beers to cocktail joints, classy hotels to dive bars in dodgy neighbourhoods, the Windy City is second only to New York when it comes to partaking of a light refreshment Stateside.

Villains, on 730 South Clark St near Soldier Field, does a list of 40 beers alongside rustic-meets-right-on American dishes like a $16 burger with bacon, aged cheddar, B&B pickles and beef fat mayo. It could be your go-to joint for the weekend - Sunday brunch includes Cola-brined brisket hash with farm eggs, and there are enough IPAs to keep you going through winter.

In the South Loop area, get your fix of all-day breakfasts and Bloody Marys at the Eleven City Diner on 1112 S. Wabash (even Seán O'Brien might be tempted to substitute his Supermacs for the Eleven City fries with Wisconsin cheddar here).

Nearby, Vice District Brewing on 1454 S. Michigan is a craft brewery with a neighbourhood-focus, industrial-chic setting and a couple of TVs - ask nicely, and they may pop something with an oval-shaped ball on.

If you wanna get down and dirty in some Chicago dive bars (and you do), get to Wicker Park and the Ukrainian Village for an afternoon.

Phyllis's Musical Inn on 1800 W. Division mixes up genuine grit, who-gives-a-sh*t attitude and vintage fridges with a surprising beer garden. 'The only place in Wicker Park that hasn't changed since 1954', it says, and the tunes are rockin' too.

Elsewhere, The Anthem is one of Chicago's best sports bars. "You take a seat and there's a bartender who's as happy to make you a cocktail to crack open a PBR tallboy," Time Out says. Amen to that.


What big sites should I see?

The Bean, Chicago

From Millennium Park to the Magnificent Mile and mouth-watering Art Institute of Chicago, the Windy City doesn't want for tourist attractions.

First off, make a beeline for The Bean, Anish Kapoor's 110-ton elliptical sculpture that famously reflects the Chicago skyline (and everybody surrounding it). It's your selfie stop, and proof that you've made it beyond the pub.

Next up, take the Architecture River Cruise (; $44) - a genius outing, in that it takes you past dozens of iconic skyscrapers (and 23 bridges) without requiring so much as take a single step.

Highlights include the 110-storey Sears Tower, the gorgeously-gothic Wrigley Building and the twin Marina City towers (which you may recognise from the cover of local band Wilco's Yankee Hotel Foxtrot album).

It's quite pricey, but the skyline justifies it.

What should I skip?

Navy Pier ( Think of it as coming to Dublin and spending an afternoon at Funderland, or the Dundrum Shopping Centre.

Yes, the pier celebrates its centenary in 2016, and a new, 50-foot taller Ferris wheel among the centennial redevelopments set to open this summer, but not even the words 'beer garden' can tempt us into a recommendation of this highly polished mix of chain restaurants and tourist traps. Fuggedaboutit.

What can I do near the stadium?

Soldier Field, Chicago

Not many Chicagoans live or socialise in The Loop, but this is skyscraper central, and you are a tourist, so why not do the full Ferris Bueller on it?

The Loop is where you'll find the awesome Art Institute of Chicago (; tickets from $25), with masterpieces ranging from Edward Hopper's Nighthawks (1942) to Grant Wood's American Gothic (1930), not to mention Impressionist classics like Van Gogh's Bedroom in Arles (1889).

Beyond that, watch out for the Chicago Theatre with its famous neon marquee sign, the Sears Tower (since 2009, known as the Willis Tower), Daley Plaza with its Picasso sculpture, Grant Park - home to Lollapalooza, and where President Obama gave his famous election victory speech in 2008, as well as The Bean (or Cloud Gate, to give its proper title) in Millennium Park.

Ultimately, it's the sense of simply being in the Loop that makes the biggest impression - similar to Downtown Manhattan. Take an 'L' ride around the business district to soak it up - the sensation of a clattery old train riding elevated lines while the 'scrapers soar above is unforgettable.

Best pizza?

Chicago is famous for its deep-dish pies (and make no mistake, these are pies - hemmed in with crumbly crusts and filled to the brim with melty cheese).

You can find great thin-crust varieties, of course, but the Windy City's best-known deep-dish chains include Lou Malnati's, Pizano's and Gino's East.

There's a Lou Malnati's on S. State and East 8th near the stadium - where the 'classic' slathers lean sausage, extra cheese and vine-ripened tomato sauce on Buttercrust. You'll be fit to hold up the All Black front row after one of those bad boys.


What tour should I take?

Architecture tour of Chicago

On any other occasion, I'd say one of Chicago Food Planet's food tasting and cultural walking tours - which give you a both a literal and metaphorical taste of off-beat neighbourhoods like Bucktown & Wicker Park over a 2-3.5-hour stroll ($47pp,

On the rugby weekend that's in it, however, plug for Untouchable Tours, the city's original gangster tour (; $30pp).

A 1hr 45 min tour in a black bus takes you on a whirlwind tour of 1920s and 30s Chicago and all of its gangster haunts (well, those that survived anyway). From Capone and Dillinger to the Valentine's Day Massacre, there's no shortage of hot spots and hits on the route, and you'll hear the story of some of Chicago's windiest politicians, too.

Definitely one for the mob…

Hit up my Spotify playlist...

Start with the city's hardest working band: Wilco (for a sampler, try 2005's Kicking Television: Live in Chicago - which squishes everything from Krautrock to alt. country into a hometown concert). Throw in some Buddy Guy and Muddy Waters for a fix of Chicago blues, add a sprinkle of Kanye, a splash of Curtis Mayfield and a dose of Dinah Washington and you should have your long-haul listening requirements sorted.

Finally, two words: Smashing Pumpkins. It's easy to forget that Billy Corgan once ruled the universe. Add 'Siamese Dream' to the playlist, and you're right back in 1993.

Where are the best cocktails?

Margherita, Big Star.JPG
Margarita at Big Star, Wicker Park.

Chicago is a cocktail town. For the ultimate, you-are-there experience, order yours in the Prohibition era Coq D'or in the basement of the Drake Hotel.

French for 'golden cockerel' (we wonder what Guy Novès and co would make of that), the bar first opened to a line of thirsty patrons after the repeal of Prohibition on December 6, 1933. Mine's an Old Fashioned.

For a grittier, hipster hit, make your way to Big Star in Wicker Park. This is the spot for tacos and ice-cold pitchers of margarita - the perfect place to wash a Saturday morning or afternoon down the tubes. The margarita ($10) is a mix of Lunazul Blanco, Lime, Marie Brizard Orange Curaco and big chunky ice-cubes, and the Mexican street food-inspired menu is a zinger too.


Ireland Fixtures: November Internationals

Ireland v New Zealand: Saturday, November 5, 3pm (Chicago)

Ireland v Canada: Saturday, November 12, 5pm (Dublin)

Ireland v New Zealand: Saturday, November 19, 5pm (Dublin)

Ireland v Australia: Saturday, November 26, 5pm (Dublin)

Get me there

Aer Lingus ( flies directly from Dublin to Chicago, while packages are available from tour operators including Tour America (, American Holidays ( and Sunway (

Trevor Brennan Rugby Tours ( has a three-night tour including flights, 4-star hotel and match tickets from €1,695pp.

Killester Travel ( has packages from €1,295pp, rising to €1,595 for the five-star Trump International Hotel (ex. tickets).

Irish citizens travelling to the US under the visa waiver program must apply for an ESTA ( travel permit. It costs $14.

For more, see

Irish Independent

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