Chicago Checklist: 5 Windy City must-dos

After a whirlwind trip to New York, I boarded an American Airlines flight to Chicago and, I’m not gonna lie, I almost cried and threw a strop. I wasn’t lifted up by the AA crew and physically buckled into my seat but…pretty close. I’m ashamed to admit this but after the bright lights of New York, I was ready for Chicago to be a thundering anti-climax. I knew I’d like it but I moronically didn’t expect to love it.

This feeling started to change when we started our descent across Lake Michigan (which looks more like an ocean expanse than a lake), met our driver called Paddy Murphy (“I’m Irish too!”) and, as the city started to unfold through the car windows, Chicago slowly but surely won me over. Walking the streets on our first night in the city, we passed stylish sets of friends drinking and dining outside under glittering skyscrapers with the slow lilt of music in the background. Chicago dances to its own beat and let me tell you, it’s infectious.

Without mentioning the cheaper-than-NYC shopping or the drool-worthy food, here’s my 5 things to do in Chicago that’ll guarantee this city gets right under your skin and becomes your go-to US destination:

1. The Chicago Architecture Foundation River Cruise, 

One of the first things that really struck me about Chicago was its skyline. The city’s architecture is a mixed bag of art deco delights nestled comfortably close to glistening skyscrapers and this mix of old and new injects the city with an eclectic character. The best (and laziest, I mean, most relaxing) way to see Chicago for first timers is by river cruise. My number one thing to do in Chi-City (ok, I know I’m not cool enough to call it that) is to jump on-board the Chicago Architecture Foundation’s river cruise through the city. Along the way the ultra-enthusiastic guide will share anecdotes about the hotels, skyscrapers, banks and other historical buildings that tower above the busy streets. Cruise past the impressive Trump Tower, the art deco Opera House with dramatic masks carved into the stone and hear all about the city’s other equally impressive wonders along the way. Even a carpark in Chicago is an architectural feat. If you do one thing in Chicago, make sure this is it.

How much? A trip on board the fast-paced First Lady river cruise costs $37.85 for 90 minutes and it’s well worth every cent. Just make sure to book in advance and, when on board, keep your camera on standby because, trust me, you’ll want to take lots of snaps.

2. The Skydeck, Willis Tower,

When you go to a new city you want to do stuff you can’t do anywhere else, right? Skydeck, step right up. Film freaks like me will of course remember Willis Tower (formerly Sears Tower) from 80s classic Ferris Bueller’s Day Off. The good news is it’s even more impressive away from the John Hughes lens. Standing at an ear-popping 1,353 feet high, the 103rd floor in Willis Tower has been renamed Skydeck and on a clear day you can see across a whopping four states. For a real adrenaline rush, go a step further and stand out on The Ledge, a completely transparent glass box you can stand on, throw poses and look down at Chicago’s streets and the other skyscrapers which look tiny in comparison.  It’s also a good way to find out if you’re more ballsy Ferris or scaredy cat Cameron (I’ll let you guess which one I was). Definitely one to tick off the ‘Travel Experiences to Do Before You Die’ list.

How much? Skydeck tickets start from $18 for an adult or buy a CityPass and get almost half price admission on five of Chicago’s most popular tourist attractions, including Skydeck.

3. Millenium Park,

Chicago has no shortage of fun things to do for free but a stroll through Millenium Park would be top of my list. This public park in the heart of the city plays host to free concerts and also acts as home to some interesting art installations including ‘Cloud Gate’ by Anish Kapoor, a huge stainless steel sculpture AKA ‘The Bean’.  Chicago has a surprising amount of greenery (including dog parks!) and Millenium Park is especially wonderful in summer time with tulips in bloom. Gorgeous.

4. The Art Institute of Chicago,

Airfare to Chicago is worth it for The Art Institute alone. Think I’m exaggerating? This mammoth gallery holds some of the world’s most recognisable art. 300,000 to be precise. Think Van Gogh, Pollock and Monet as well as one of the most famous paintings of the twentieth century and one of my all-time faves, Edward Hopper’s ‘Nighthawks’. Actual artgasm. Unsurprisingly, the curator told me the most popular work of art is the instantly familiar ‘A Sunday on La Grande Jatte’ by George Seurat AKA the painting Cameron completely spaces out staring at (yep, another Ferris Bueller reference). I also loved a dreamy Georgia O’Keeffe, the Dali collection and seeing American Gothic in the flesh gave me chills. CHILLS.

How much? The $23 admission seems pricey but you could easily spend all day here.

5. Take a swing class at Big City Swing,

For an authentic American experience and something I for one definitely wouldn’t do at home, go for a swing lesson at Big City Swing in The West Loop. They offer classes for beginners of all ages, couples getting hitched and basically anyone who wants to learn a few moves. And don’t worry, you don’t have to be an ex-Black Swan to swing. I found dancing with strangers to be completely awkward at the start but I was laughing (possibly with shame) at the end of it. Am I now a master of swing? Nope. Can I say I had too many glasses of wine on a heady night in Chicago and did a swing class with 10 randomers? YES. Now that’s a travel memory I wouldn’t trade for anything.

The important stuff:

Getting there: I flew with American Airlines from Dublin to Chicago O’Hare which is priced from €645pp return, including all taxes and charges. This direct daily flight runs from April to October. For more information or to book, go to or call 01 602 0550 from Ireland.

Stay: I stayed at the Park Hyatt Chicago and didn’t want to leave. This sophisticated hotel ticks all the right boxes with slick décor, free wi-fi, two designer-decorated suites and a central location that’s hard to beat. The hotel’s NoMI Kitchen restaurant has a garden terrace so you can grab breakfast and watch the city’s streets below on a sunny day. Go to for more info.

For more inspiration for your trip to Chicago, go to


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