Sunday 21 July 2019

Chicago: 21 top things to do in the most American of cities

From brilliant burgers to baseball at Wrigley Field, Chicago is one of the world's great city breaks

Downtown Chicago
Downtown Chicago
Gospel breakfast in Chicago
Chicago lake tour
Chicago Bean
Art Institute of Chicago
Chicago River tour
Wrigley Field in Chicago
Mark Evans on The Ledge, Willis Tower
Pizza at Lou Malnati's in Chicago. Photo: Choose Chicago
Dana Hotel Chicago
United Airlines Polaris

Mark Evans

'Chicago, that's my home town,' Frank Sinatra crooned in one of his best-known American ballads. You can see why the New Jersey native felt at home here.

This is the most American of US cities - to me, a mix of the quality of life across the border in Toronto combined with New York's energetic canyons of skyscrapers. Great food, music and friendly Midwesterners make it a city that could occupy you for weeks. Here's my shortlist of what to do in just a long weekend...

Day 1

Dana Hotel Chicago

The noon flight from Dublin on United Airlines will get you into town in the early afternoon - with plenty of time to get your bearings. First port of call is the hotel - and I stayed at the Dana Hotel & Spa (; rooms from around €200 per night) in the heart of the city on State Street.

Many of the 216 rooms (rising up to 26 storeys) have great views over the skyscraper-laden downtown area. Rooms are trendy, with floor-to-ceiling glass, shower in the middle of the room and fast in-room Wi-Fi.

There's a buzzing bar, it's a nice home-from-home and the friendly staff have plenty of tips on what to do in town. First night, and with a bit of jet lag, it's wise to take it easy. The hotel has a celebrated seafood restaurant, Portsmith, and it's typically American, with a great choice of Atlantic-coast shellfish and local varieties of fish.

Nightlife: Before heading out, be sure to check out the hotel's rooftop terrace. It's in demand in the city and it's easy to see why, with its young, trendy crowd and superb views over the downtown area.

For a little nightcap, head to Rossi's, just down a few blocks on 421 North State Street. It's a classic American dive bar, with an eclectic crowd of suits and bohemians, so you'll be sure to strike up a conversation.

Be sure to try a shot of the fierce local firewater, Malort. It's never caught on anywhere else. Taste it and you'll realise why.

Day 2

Chicago River tour

Chicago was the first in the world to construct a skyscraper (a massive 10 storeys high), and inspired other cities like New York to go high-rise.

The best way to see the dizzying array of skyscrapers - from the ornate Wrigley and Chicago Tribune buildings to modern behemoths - is along the Chicago River.

Pick of the boat tours is the Chicago Architecture Foundation Center River Cruise on board Chicago's First Lady Cruises ( An expert guide will show, over an hour and a half, how the city started off in the 1830s and rebuilt in a big, big way after the great fire of 1871.

Lunchtime: Locals are proud of two things. One is their hot-dogs (with white onions, pickle relish, a dill pickle, tomato slices or wedges, pickled sport peppers and a dash of celery salt - but never, ever, ketchup). The other is deep-dish pizza. Locals swear by Lou Malnati's Gold Coast (, which is a great place to get stuffed without breaking the bank, and has been going strong just north of downtown since the 1950s. One tip: order small to start, portions are enormous.

Wrigley Field in Chicago

Sightseeing: To me, baseball's a bit like hurling on sedatives, but if you're in town, you really have to take in a game. Why? Purely because of Wrigley Field, one of the great stadiums - in any sport - on this planet.

Old and retro, you half expect to bump into baseball players of yesteryear like Babe Ruth or Joe DiMaggio here. Built in 1914, it has been renovated but the feel is the same - the scoreboard is still changed by hand and it's a place to people watch as the local team, the Cubs, go to bat.

It's a riot of noise, popcorn and beer, but even if you know little of the game, this is quintessential, and unmissable, America ( for tickets).

Dinner: Given its location in the heart of the US, the city has a long history in the meatpacking industry - and decades of serving up great steaks. The very fancy Chicago Chop House ( is one of those timeless restaurants, with 1,400 photos from the past adorning its walls. It's the go-to place if you want a good cut, with an array of choices from wet-aged and dry aged to prime and bone-in-rib specials. Recommended for a romantic night out.

The Loop, Chicago

Nightlife: African-Americans migrating for work from the Deep South brought their music to Chicago, and the city remains a great place to catch the blues. North of downtown is the celebrated Kingston Mines (, the oldest continuously operating blues club in town, and it's what I can only describe as Jools Holland-style - with acts rotating between the two adjacent stages. The night I was there, it was old Tina Turner anthems on the left, Muddy Waters classics on the right. Nice atmosphere and some rocking music.

If you need a nightcap, The Boss Bar ( is a lively pool, beer and grub spot that opens till 5am some nights.

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

Day 3

Chicago at sunset. Photo: Deposit

There's nothing like a church service after a night out - and this is nothing like a church service, it's the World Famous Gospel Brunch at House of Blues. Soulful music (think Sister Act) from an energetic pastor and his young choir make this a Sunday with a difference. There's audience participation, hymns with fun and funk, chicken, heavenly Cajun food and a buffet to stuff you up. It's vibrant, it's fun, it's got beer. Take me to church... (

Sightseeing: You'll probably be stuffed after the brunch, so a bit of lazing around is in order. The popular Navy Pier entertainment centre, with some rides for children, was built in 1916 and renovated in the 1990s. It's also the home of the Classic Lake Tour with Shoreline Sightseeing. Touring the vast Lake Michigan (bigger than the Irish Sea, folks!), you'll get a panoramic view of the city skyline and see locals at play in anything from tiny boats to super-yachts. If the sun is shining, it's a lovely way to laze around, but don't forget the camera (

Nightlife: The Purple Pig (, on swanky North Michigan Avenue, is the in place, and critically acclaimed, with long lines to get in. And it's very different - fried pigs' starters (delicious, actually), pork tail, offal, as well as more regular meat and fish, served up tapas-style. Be aware that portions are US-style: enormous. A buzzing spot for the adventurous diner.

Situated in a swanky area near Navy Pier, Winter's Jazz Club (, although relatively new, is like stepping into a 1950s Beatnik hangout. A supper club, it's chilled, you're right up beside the musicians and there's table service with a good cocktail menu. A great couple's spot.

A little drink after? Richard's Bar, on the west side of town, at 491 North Milwaukee Avenue, is now in my worldwide top 10 of bars. Resolutely Italian, it's got GoodFellas and Rat Pack photos on the wall and Dean Martin on the jukebox. The kind of place where Tony Soprano would spend the day. Recommended.

More: Chicago: A perfect day in The Loop

Day 4

Chicago's skyline.

The flight back home is in the evening, so there's still plenty of time to see the sights, and you'll catch everything - and even three neighbouring states - from Skydeck Chicago at the top of the 1,450-foot Willis Tower.

The tower is the Western hemisphere's tallest skyscraper after One World Trade Center in New York and it was here that Ferris Bueller took in the glories of the city in the Hollywood movie. From the 103rd floor, you'll get amazing views. Try, if you dare, one of the glass boxes jutting out 4.3 feet over the streets of Chicago for a terrifying vista. It's a bit nervy at first, knowing that three inches of glass is all that's separating you from a very fast descent to the street 1,353 feet below (

Chicago Bean

Down below, don't miss beautiful Millennium Park and its Cloud Gate sculpture, better known as The Bean, for cool pictures of the reflected skyscrapers. Close by is a source of pride for locals - the Art Institute of Chicago.

Truth be told, the only thing I know about painting is gloss or matt, but this historic museum of sculpture and art impressed even this philistine. It's home to the greatest collection of Impressionist paintings outside of Paris, and also features more modern works by the like of Warhol and Picasso. It's a beautiful place, and even I learned something - I'd recommend it to anyone.

Art Institute of Chicago

Lunchtime: Follow the locals to Revival Food Hall (, a sprawling converted building with a variety of choices (the burgers are amazing).

For last-minute souvenirs, bargain-filled department store Marshalls on North Michigan Avenue is a few minutes' walk from the hotel, or if you have a bit more time it's designer bargains ahoy at Nordstrom Rack on North State Street.

And if you spend longer than a weekend, check out the outlying outlet malls or simply check out the dizzying mix of stores along downtown's Magnificent Mile.

Here's to next time...

Getting there

United Airlines Polaris

I travelled as a guest of United Airlines, which operates summer seasonal flights (until the end of October this year, and back next spring) from Dublin direct to Chicago, with a flight time of just over eight hours out, and slightly less back.

I was lucky enough to fly its Polaris business class (inset), with lie-flat bed (I slept all the way home), Saks Fifth Avenue bedding and stylish dining. There's a full bar, restaurant and shower rooms in the upmarket Polaris lounge in the city's O'Hare airport.

Business class fares from Dublin to Chicago start from €2,360 including tax and charges - definitely worth looking at for a honeymoon or memorable trip. At the cheapest end of the scale, the basic economy fare (without check-in bag) starts from €402, bookable until November 5 and subject to availability.

With a bag, it costs from €482.70 (

Getting around

Chicago's CityPASS is a good way of seeing the sights at a discount, with 51pc off the top five attractions and you often get to skip the queues, saving time in the process ( chicago). For a quick overview of the city, tours from one-day up are on, and you can find more ideas and suggestions for things to see and do at the official tourist site on

Read more:

The Chicago Bucket List: 39 things to see, do and eat in the Windy City!


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