WE'VE all had a pretty rubbish last couple of years. So, when I was approached to visit Chicago – well, what would you do?
For those that don’t know, Chicago is the largest city in the state of Illinois. It’s also a city firmly based on the southwestern side of Lake Michigan, which boasts the largest collection of freshwater dunes in the world.
Lake Michigan is also the only Great Lake – out of five – that is located completely within the United States. The other four Great Lakes (Superior, Huron, Erie, and Ontario) share borders with both the US and Canada.
But you’re not here for facts about a big ol’ lake. You’re here to find our whether Chicago is worth jetting off to.
Day one – everyone loves art deco, right?
On Wednesday, May 11 at noon, it was touch down at Chicago’s O’Hare Airport. On a personal note, it was the first time I'd been to the States since the mid noughties. I’d been a couple of times before, most recently to New York City when I was a kid with my dad.
What’s the first thing you do when you get off the plane? You head straight to your hotel to freshen up.
I can’t sleep on planes. Honestly, it’s a curse and I envy those who can – like the elderly envy the young.
After a short journey along the 290 Interstate (I know, so cool!), myself - and five others - arrived at Canopy by Hilton, in W. Jackson Boulevard.
Now, if you love your history, this building, located at the heart of Chicago’s Financial District, was once the headquarters of the Northwestern Railways, according to hotel manager Sarah Becker.
Chicago is historically famed across the US for its railway industry, so I can assure you, it’s a big deal. And this was highlighted throughout the hotel with imagery – and doffing of one’s hat – to the city’s industrial past.
The design of the hotel takes you back to the roaring 1920s with its art-deco style (yes, I like art deco too, everyone does – we’re not unique). In fact, that art-deco style was spread right across the city centre; it was wonderful.
With my suitcase tucked away next to my king-size bed in my five-star room on the tenth floor, the first stop was my one true love – food. More specifically, the Revival Food Hall, in South Clark Street.
If you’ve ever been to Manchester, you may have visited the Arndale Food Hall. The Revival is like that, but amped up. It was incredible. I went for an Indonesian dish. A spicy tofu delicacy with rice. It was sublime. I remember telling the group: ‘Nothing will top this.’ Spoiler: it was easily beaten, but we’ll get to that later.
After some rest, my gluttonous side was emerging once more just in time for our arrival at Eataly, in East Ohio Street. It’s a vibrant Italian marketplace that features a plethora of cafes, counters, restaurants, and even a cooking school. If you’re into red wine, it’s a must!
The sun had set on my first day in Chicago and our group headed along the Riverwalk to watch Art on theMART 2022 Spring Program.
It was an art installation projected onto the city’s colossus Merchandise Mart and featured global warming concerns. It was mesmerising to watch, and would be the perfect spot for a date, but admittedly jet lag was settling in.
Day one pit and peak
Pit of the day: A member of the group left her passport on the plane and only discovered this realisation at security and customs. Haunting at the time, but we can laugh about it now. I won’t say who it was…
Peak of the day: As soon I got some free time, I was off to see the film locations for the Dark Knight’s (2008) opening bank robbery sequence, which was luckily one block away from my hotel. Always do what makes you happy, even if it is a bit 'nerdy'.
![Dorset Echo: My [poor] attempt at recreating the Joker-on-the-corner shot during The Dark Knight's (2008) opening bank robbery scene](/resources/images/13810439.png?type=mds-article-620 "Dorset Echo: My [poor] attempt at recreating the Joker-on-the-corner shot during The Dark Knight's (2008) opening bank robbery scene")
Day two – a trip through the ‘Grand Canyon’ of the Chicago River
Fresh from eight hours sleep and a feast from the hotel’s talented chefs – which included a belly full of avocado on toast, strawberry smoothies and enough fruit to open my own greengrocers – we hopped onto Chicago’s First Lady for the city’s famous Architecture River Cruise. Again, if you like history – stay tuned for this.
The man with the tannoy was quick to point out that every individual building along the Chicago River has a deep-rooted meaning, whilst describing the journey as a ‘trip through the Grand Canyon of Chicago'.
The Wrigley Building was a forerunner in Chicago’s ‘magnificent mile’. Built in 1921 after a huge cash boost from chewing gum industrialist William Wrigley Jr, the building lured commercial investment to the city’s north side.
Another notable structure is The Marina City, or the ‘Corn Cobs’, built in the early 60s. These ‘cobs’ broke away from the Minecraft-esque, ‘boxy modern’ style that so frequently became prominent within the city’s skyline.
I can write all day about each building, but my word count would be ridiculous. However, I will give a shoutout to Chicago’s Movable Bridges. The city has more movable bridges than anywhere else in the world. Most bridges over the city’s river are trunnion bascule, known throughout the world as ‘Chicago style’. The French word ‘bascule’ means teetor-totter.
Also, I did laugh when I saw how grand and tall Trump Tower is. Perhaps Donald is compensating for something… who knows.
Note: if you’re going to take the Architecture River Cruise, stay hydrated, and wear a cap and sunscreen. It’s 90 minutes and those buildings reflect. In fact, if you’re visiting Chicago around May time onwards, a good rule of thumb is to always have those items on you.
After saying farewell to the First Lady, we rocked up to the Italian sandwich restaurant, Al’s Beef. You can get it hot (with giardiniera peppers) or sweet (with sweet peppers); dry (no gravy), wet (extra gravy on top), or dipped (the whole sandwich takes a bath).
No matter how you order it, you’ll be getting a taste of one of Chicago’s most famous creations – the Italian beef sandwich. Plus, the restaurant is a hotspot for celebrities.
Then it was a quick uber to Millennium Park which houses the sophisticated outdoor concert venue Jay Pritzker Pavilion, the urban oasis Lurie Garden, and of course Cloud Gate – nicknamed ‘The Bean’.
During the evening, we tucked into Greek cuisine at Lyra. Although, the restaurant was the most high-end of the eateries throughout the trip, the dark interior and mood lighting created a relaxing vibe. The restaurant is regularly packed-out, so try to book ahead.
The day ended after watching the Hubbard Street Dance Chicago: RE/UNION at the Harris Theatre. Now, I’m not a massive fan of interpretive dance, but the strength, speed and timing of each performance had me gripped.
A personal favourite was a dynamic portrayal of Minus 16 by Ohad Naharin. YouTube it – you won’t be disappointed.
Day two pit and peak
Pit of the Day: I got sunburnt due to my Irish and half-ginger heritage. Wear sunscreen!
Peak of the Day: Hearing an abundance of interesting facts about each building along the Chicago River. It’s no wonder the city is so famous.
Day three – Upside down on top of the world
After a quick breakfast and a walk across the road into the iconic Willis Tower, we started the day with a tour of the lower-level interactive experience – and then a 40-second lift to the 103rd floor atop of the breath-taking, thrilling Skydeck observatory. It was a ‘wow’ moment.
103 floors up atop the willis tower in chicago #skydeck pic.twitter.com/w71enLnNaZ
— sam mckeown (@SamMcKReporter) May 23, 2022
With clear skies out of the wide windows and with the soundtrack of the bustling city below - we were so lucky, and we knew it.
There are five glass floor balconies extending 4.3 feet outwards; made up of three layers of half-inch thick glass laminated into one seamless unit. So, me being me, I decided to do a headstand.
After my theatrics, I quizzed the cleaner. He said he had been working in the tower for 18 years; he has always felt safe when cleaning the platforms; and said he asks to work every July 4 (Independence Day) because ‘when night falls the view is spectacular’.
Now, I’ve been up to the top of the Empire State Building, but the Skydeck beats it hands down. There was no rush, you weren’t squeezing past people - and the 360-panoramic view of the city as well as the stunning Lake Michigan should not be missed.
Late morning, it was our group’s first trip outside of the city centre to Wicker Park, Bucktown.
It’s one of Chicago’s eclectic and hippest neighbourhoods. North Milwaukee Avenue runs right through the area, which is scattered with trendy shops, and a variety of 80s and 90s throwbacks. It was like being in a Taika Waititi film. I would compare it to Camden in London, or the Northern Quarter in Manchester. And it’s a 15-minute train ride back into the city centre via the Blue Line.
After getting our steps in, it was time for some lunch at Bang Bang Pie and Biscuits, in North California Avenue. From cakes, pies and sweet or savoury biscuits (it’s an American thing, I’d never heard of it either), there’s more than enough options for meat eaters, and vegans.
After an elevated tour of Bucktown and into the city centre via the Blue Line, it was time for rest in preparation for what would be my favourite restaurant of the trip.
Located to the heart of River North is the metropolitan Tortoise Supper Club, serving steaks, chops, and fresh seafood. The family-owned venue always has live jazz acts. This is coupled with the dark mahogany and ambient lighting mixed with the sound of soft, live jazz. All that with a large glass of red wine – well, it was bliss. Note: The attire is smart casual.
Day three pit and peak
Pit of the day: Admittedly, I was telling myself I was too tired before heading up to the Skydeck, and my tiredness turned to elation after I’d been up there for 10 seconds upon realising where I was. I think we’re all guilty of getting into our heads sometimes. It’s something we all need to work on. Be more in the moment.
Peak of the day: Oh my days, the food at Bang Bang Pie and Biscuits was other worldly.
Day four – A busy, busy bee desperately needing a wee
Now, I would say this was one of the busiest days of my life.
Do you like museums? I love a museum. We’re all culture vultures at heart – but I think we’re all so wrapped up with that black-screened rectangle we hold in our hands for most of the day.
First stop was the Museum of Contemporary Art. Oddly enough, the museum housed a variety of expressive installations tackling modern-day issues such as homophobia, racism and technology addiction. And at its centre was an exhibition from internationally renowned Chicagoan Nick Cave.
After an art binge, we set off to Andersonville – voted the second coolest neighbourhood in the world (second only to Nørrebro, Copenhagen).
A neighbourhood on the city’s north side, Andersonville is known for its Swedish roots, historic architecture, and bustling urban main street, Clark Street.
It's also home to one of Chicago’s largest LGBTQ+ populations. Andersonville is a community full of pride and a commitment to equality. Notable stores include The Brown Elephant and Foursided. Also, grab something to eat in Michelin-rated and eco-friendly Gadabout, then grab a beer at Simon’s Tavern – one of the oldest taverns in Chicago.
After a quick mooch around the neighbourhood, it was an uber ride back to the hotel to freshen up, before heading out for cocktails at Tanta’s Rooftop, in West Grand Avenue.
Tanta shares the flavours and culture of south America, serving authentic Peruvian dishes and beverages in a casual downtown setting.
The second-to-last destination of the day was dinner at Galit, a Middle Eastern Restaurant in Lincoln Park (yes, we too wondered whether Linkin Park had ever been to Lincoln Park).
The menu focuses on dishes of the Middle East and Israel’s immigrant cuisines. We were stuffed – you get your money’s worth.
It was finally time for what would be the best event of the trip. Less than a block away from Galit (or 300 metres for those in the UK) is Kingston Mines Blues Club.
toronzo cannon playing just after midnight at kingston mines on may 15 2022 #chicago pic.twitter.com/LcPGVZQGUN
— sam mckeown (@SamMcKReporter) May 23, 2022
Founded in 1968, Kingston Mines is the largest and oldest continuously operating blues club in Chicago. It provides an authentic atmosphere with stages either side of the main bar. The later the night draws, the more the crowds pour in. Truly, a must-go destination – that is if you can get in of course. I’d advise booking and getting your name on the list.
Day four pit and peak
Pit of the day: Due to the constant hydrating and busyness of that day, on our ride to Andersonville we had to pull over so I could have a wee in a bush. Honestly, I was bursting. Shout out to Bella and Heat magazine’s Kay Ribeiro for attempting to calm me during what was one of most agonising moments of my life.
Peak of the day: It’s got to be Kingston Mines. It’s a venue that transports you to a place where you forget everything going on with the outside world. It was outstanding, and the place to be for music lovers.
Day five – bravo, Chicago, bravo
The morning consisted of checking-out. We’ve all been there; we all hate it - let’s move on.
For lunch it was deep-dish pizza dining at Giordano’s, in North Rush Street. You can’t go to Chicago without having a deep-dish. Each pizza is slow baked to flaky perfection and filled with flavoursome ingredients. It’s the real deal, unlike those mini-Chicago town knockoffs you can grab in Aldi and Lidl, respectfully.
Before I knew it, we were hoping onto our United Airlines flight home to Heathrow. I should note United was probably the best airline I’ve ever flown with. They gave me two lots of pancakes with raspberry sauce for breakfast - massive win. I even had time to watch the Dune remake and House of Gucci.
My two cents
A few other destinations to hit up in Chicago is the American Writers Museum and The Art Institute of Chicago – the latter houses original pieces from a host of artists including Vincent Van Gogh, Pablo Picasso and Salvador Dali.
Infamously, the city was the stomping ground of prohibition-era mobster Al Capone - and there’s plenty of sightseeing in that regard.
Also, for any baseball fans, Chicago is home to the Cubs, that play at Wrigley Field, and the White Sox, that play at Guaranteed Rate Field – better known as the Cell (formerly Cellular Field).
The city centre is manageable by foot, but if you’re going into the outer areas, I'd recommend the train. It’s a measly three dollars per journey, and if you’re like me and love people-watching, it’s the perfect thing to do.
As I’ve previously said, I’d been to the States before. New York in 2005 and Florida in 2004. For me, Chicago trumps New York City. I would choose the Illinois capital every time. I remember my experience of the Big Apple was one where I felt like cattle, while the Windy City offered a more liberal, calmer experience.
For more information on the above, visit: www.choosechicago.com
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