48 hours in Chicago: a 'second city' with civic pride forged in hard work
Chicago The Riverwalk: Heart Of The
The City of The Big Shoulders is an apt name for Chicago, birthplace of the skyscraper and cradle of modern architecture.
It is unabashedly founded on hard work and money – and the wealth that flows through it supports a thriving theatre and arts scene and several major universities.
It has a chippy, scrappy civic pride - The Bear is the latest (and greatest so far) in a long line of movies and television shows that lovingly portray Chicago in all its gritty, glorious modernity.
It is like no other city in America.
If you like to get an overview of a city by taking an open-top bus tour, you’ll find Chicago’s First Lady Architecture River Tours an even better way to navigate the Windy City.
The affable and knowledgeable guides are volunteers from Chicago Architecture Centre (and they don’t accept tips – but encourage donations to the centre, which is a heartening dedication to the cause).
On this tour, you’ll learn that the fire that decimated the city in 1871 was a key turning point in its history. This tour gives a genuine insight into the character of Chicago.
The first skyscrapers came as a result of the rebuilding – the skyline you see, with its Mid-century Modern landmarks, is the silhouette of a phoenix arisen from the ashes.
Bueller’s Day Off wasn’t complete without a visit to The Art Institute of Chicago, and your trip won’t be either.
There is something ineffably beautiful about the dreamy sequence in John Hughes’s teen caper when everything slows down as the kids drink in the work on display at this world-class gallery.
You could easily spend 48 hours just in this building, with its magnificent collections. If you’re interested in art, spare some time for The Museum of Contemporary Art on Washington Square too.
In the 1990s, the local Puerto Rican community resisted being ousted by gentrification and instead literally planted their flag (a public art installation which is two giant flags a mile apart) in the area which has been little Puerto Rico for decades.
This mile near Humboldt Park has developed into a vibrant Latin Quarter, with a walk of fame for Puerto Rican heroes and heroines, a cultural centre and many murals depicting the life, history and dreams of this community.
The locals express an affinity with Ireland, seeing parallels in the two countries’ struggle for independence.
- Best enjoyed with the charismatic local guide Eduardo Arrocho. Book through paseoboricuatours.com
In the months when it’s open, The Riverwalk is the heart of the city.
Enjoy a cocktail at The City Winery (there are several locations so make sure you’re at the Riverwalk) looking up at the iconic Wrigley Building and watching Chicago at work and play.
The Dearborn in the theatre district serves elevated classics (steak, salad, fish, protein bowls) with the best ingredients.
Irish-owned and run by two sisters from Galway, Amy and Clodagh Lawless, the delicious comfort food is prepared by a chef who left Michelin-starred dining to have the autonomy to make himself, his team and his diners happy (sound familiar, viewers of The Bear?)
Not a sister restaurant but run by the Lawless brother, The Gage is right opposite the Art Institute on Michigan Avenue so if you’re ready to rest and be replenished in the middle of your day, this is equally good for lunch as for supper.
It describes itself as gastropub but the service is more white tablecloth than rustic - the seafood tower is a speciality but it’s equally good for a classic steak.
If shopping is your thing, The Magnificent Mile is for you.
It’s an upscale street where the buildings alone are things of beauty.
900 North Michigan is a playground for the classy consumer but all along here you’ll find palaces of consumerism to widen your eyes.
Second City comedy troupe has given the world some of its most beloved comedians and honed the art of improv.
Those in the know agree that the apotheosis of the art is the show TJ and Dave.
These two actors, masters of improv and lifelong friends go on stage and engage with the audience to create something new each time, improvised from scratch every single night.
It’s an experience that captures the magical intimacy and immediacy of live theatre.
TJ and Dave tour the world but Chicago is their hometown so try to catch a show while you’re there. It’s guaranteed to be once-in-a-lifetime.
The SkyDeck of The Willis Tower (the tallest building in the Western Hemisphere) offers 360 views across the city from above but you don’t need to scale the heights to explore the city’s architectural legacy.
Take in the Robie House, one of Frank Lloyd Wright’s early works before crossing the road to the beautiful Rockefeller Chapel.
Designed to be non-denominational and hosting many free activities it feels surprisingly modern and welcoming for a building that is nearly a hundred years old.
In this same Hyde Park area is The Museum of Science and Industry - this unpromisingly named building contains the most fun and engaging exhibits - unmissable if you have a kid, or ever were a kid.
A boutique hotel in a terrific location, The Godfrey is walking distance from many main attractions.
Chicago has just been voted Best Big City in The US by Conde Nast Traveller for the seventh year in a row and a large part of its appeal is its walkability.
The Godfrey has spacious rooms with classic design that’s restful on the eye and it’s close to The Magnificent Mile and The Loop and an easy stroll to the river and many of the attractions.
The IO Godfrey Rooftop Lounge on the hotels’ fourth floor attracts a glamorous crowd year-round, thanks to its retractable roof. Book for drinks or meals and dress to be seen.
Aer Lingus flies direct twice daily from Dublin to Chicago year-round.
Both flights are at civilised times, which makes it an agreeable hop for a quick getaway. aerlingus.com Chicago is not famous for its clement weather. Check with choosechicago for the best times of year to visit but Spring and Autumn are smart bets. We enjoyed a heatwave in late September and of course the St Patrick’s Day celebrations are world-famous.
The best way to get around Chicago is via the L train which is cheap and easy to use.
The CityPass is invaluable as a way of prioritising attractions, saving money on tickets and priority access.
- Mary Kate O’Flanagan was a guest of Choose Chicago and Aer Lingus