A whistle-stop tour of Chicago (with all the best places to squeeze in)
From sampling just about every cuisine under the sun to craning your neck to see some of the most impressive skyscrapers in the world, here’s how to make the absolute most of five days in the Windy City.
From Cork to Dublin and Dublin to O’Hare International Airport, I arrived in the Windy City to clear blue skies. Exhausted and excited in equal measure, I hopped into the hotel transfer (which was, inexplicably, a stretch limo-truck hybrid) and spent the ensuing 45 minutes staring wide-eyed out the window.
I’ve only been Stateside once before, so the novelty hadn’t quite worn off. Big yellow school buses, skyscrapers that were tickling the clouds, and stores like Trader Joe’s, Walgreens and 7/11s dotted on every street corner — all these stereotypically American things that wriggle their way into your consciousness through television and your favourite vlogger’s day in the life.
I went in the springtime, just before travelling from Ireland to America became the daunting task it is at the moment and right after the announcement of the new head of the Catholic Church, proud Chicagoan Pope Leo XIV. For a city universally known as windy, the locals informed us that we made it just in time for a ‘Proper Chicago Spring’ — clear blue skies, heat in the sun, and a soft breeze in place of the more severe gusts.
The Magnificent Mile—basically, the commercial district—is known for its beautiful displays of tulips every spring, with over 100,000 Dutch bulbs lining the streets in just about every colour you can imagine. The streets were litter-free and the people were warm and friendly. First impressions were very, very good.
Given that our trip was extremely fleeting, we had to streamline each day and make sure we were covering all the bases, and I think we did a mighty fine job. If you’re planning a trip to Chicago, here are the places to bookmark…
Where to stay
Hotel EMC2 is extremely well placed for a flying visit during which you want to see as much of the city as possible. It’s right next to the Theatre District, Field Museum of Natural History, Art Institute of Chicago, and all the shops and restaurants of the Magnificent Mile.
It’s also super high tech, with an Alexa in the room and robots roaming the halls bringing fresh towels and water to guests around the hotel. Beautiful art lines the walls and the staff put you instantly at ease after a long day of travelling or sightseeing.
I can also vouch for the food here, having enjoyed dinner on night one and breakfast each morning in The Albert. I’m still dreaming of the poached peaches and ricotta with honey on crusty sourdough — a concoction I’ve been attempting to recreate but haven’t quite mastered yet.
Famous attractions
We made great use of CityPASS, which essentially gives you discounted access to tourist attractions and makes it quick and easy to book online through their app. The options for Chicago were plentiful, but here are the ones I went for…
Skydeck Chicago
Located in the iconic Willis Tower, America’s highest observation deck was quite a surreal experience. You fly up 103 floors in an elevator (my ears had popped by level 56) and step out 1,353 feet up, with the entirety of the city stretching out all around you. The Ledge extends out from the building, so you’re standing on 1.5 inches of glass and nothing else. Photo ops abound, and you can stand in the very spot where Ferris, Cameron and Sloane stood in Ferris Bueller’s Day Off.
The Art Institute of Chicago
So nice I went twice (no really, I did), the Art Institute is a place you could spend hours wandering around — it was a true highlight of the trip.
Highlights for me included seeing Edward Hopper’s Nighthawks in the flesh, Grant Wood’s American Gothic (I was in it for the The Rocky Horror Picture Show reference), and the beautiful Impressionist Woman at Her Toilette by Berthe Morisot. You’ll also find work from Picasso and Monet, Warhol and van Gogh, all of which will induce goosebumps.
I was particularly moved by The Child’s Bath by Mary Cassatt, a beautiful oil on canvas portrayal of familial closeness that made my eyes misty and prompted me to call my mother for a chat and pick up a couple of its prints in the gift shop.
Sightseeing (with a twist)
What I loved most about Chicago was the many different avenues through which it can be explored. It allows you to get under its skin in a unique way, and experience it at a more intimate level. We even went on a Chicago Greeter tour led by a little old lady around her neck of the woods, Wrigleyville, where she took us on a spin of the L-Train and spun yarns of what the buildings looked like back when she was growing up.
Chicago’s First Lady Architecture River Cruise
This is a really engaging 90-minute architectural tour experience guided by a local volunteer that will leave you with a pretty solid knowledge of Chicago’s skyline and architectural styles in general.
They share stories of the legendary figures who designed and built the city, including Jeanne Gang, the architect responsible for the tallest skyscraper in the world designed by a woman, the St. Regis Chicago.
Bobby’s Bike Hike West Side Foodie Tour
The words ‘bike’ and ‘hike’ don’t inspire much excitement in me, and I will say I baulked when I first saw it crop up in the itinerary. But shockingly, I thoroughly enjoyed it — though my hands did get sunburnt from gripping the handles for dear life. As the name suggests, it’s a cycling tour of food stops around the city, and it’s a great way to see some of the lesser-known neighbourhoods and more niche food spots.
We stopped by three restaurants, and the cuisine sampled included Mexican tacos, Polish pierogis, and Roman pizza. I will reiterate: I am by no means a strong cyclist, but if I can do it, anyone can.
Ravenswood Malt Row
Hands down, my favourite part of the trip was our tour of Ravenswood Malt Row, a neighbourhood peppered with independent businesses, creative pop-ups, and most enticingly, lots and lots of craft beer breweries, Chicago’s first (legal) post-prohibition distillery, and a stunning winery.
Our tour stopped by three such spots: Begyle Brewing, Dovetail Brewery and KOVAL Distillery, and the level of passion emanating from the staff in all three locations was genuinely very gorgeous to see. I particularly enjoyed the culture around drinking in these spots, with people working from home with a pint at their elbow, Mommy and Me group meetings circling in the beer gardens, and Yoga and Happy Hour events advertised in the bathrooms.
Where to eat and drink
The Dearborn
Obviously, the Irish will always sniff out their fellow Irish wherever we are in the world, and this venture by Galwegians Amy and Clodagh Lawless was a must. The Dearborn has the spirit of the American tavern with touches of Irish hospitality (and Celtic symbols!) present throughout. Ideal for lunch, the portions are unsurprisingly massive, and I cannot endorse the Caesar salad enough. A side of fries and a glass of Pinot are not essential, but come highly recommended.
Crosby’s Kitchen
Another fantastic lunch option, Crosby’s family-friendly American grill has all the classic comfort foods (hello bubbling mac and cheese), wood-roasted half chicken straight off the rotisserie, and French dip sandwiches to rival those of The Bear.
Duck Duck Goat
Located in Fulton Market, which is filled with so many incredible dining and drinking options, Duck Duck Goat is a Chinese-American restaurant made for celebrations and sharing food around a lazy Susan. Hand-pulled noodles, house-made dumplings, pickled cucumber salad and fiery shrimp — we essentially got one of everything and kept eating until we were stuffed.
Bronzeville Winery
A little bit out of the way but totally worth the journey for the vibes alone, Bronzeville Winery is a Black and female-owned business that reflects their diverse and vibrant histories beautifully through art, hospitality and a top-tier menu. The Creole salmon pasta was incredible, and their ‘Women in Wine’ tasting flight really caught our interest.
Rosa’s Lounge
If you’re looking for after-dinner drinks and live music, Rosa’s Lounge pays tribute to blues music and is the kind of location you won’t want to leave in a hurry.
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