“Do you think about me now and then? ’Cause I’m coming home again.”
There are certain songs that just belong to a place. For me, Kanye West’s Homecoming will forever be Chicago. And yes, I’m fully aware Kanye is a little more controversial these days than he was when the song came out, but you cannot deny the man had some hits.
The whole song is essentially a love letter to Chicago, disguised as one to a girl called Windy. He talks about leaving her to follow his dreams, but she’s always there in the background, pulling him home. Having grown up in the Chicagoland area before leaving for New York and eventually London to pursue a career in fashion, I get it. Chicago has always been the place I come home to. I even lived there on and off during my Gossip Girl years. We only filmed for eight months of the year, which meant four glorious months of hiatus to enjoy summertime Chi.
Now, every summer I bring my children back for their own little dose of Midwestern life, splitting our time between my parents’ house, about twenty minutes outside the city, and their place on the lake in Michigan. It’s completely different to their London existence, and I love watching them compare the two. According to them, they’re also “famous in Chicago.”
Their reasoning is that loads of people here know who they are, while they have absolutely no idea who any of these people are. Which is actually quite hilarious. Although, annoyingly, they do have some evidence to back up their claims. For the past few years, I’ve presented a Back to School fashion segment on Daytime Chicago, and they’ve appeared as models. One of my daughter Wavy’s classmates recently came up to me and said he’d heard Wavy was famous in Chicago and had “been on TV a couple of times.” I mean… he wasn’t wrong.
This year, said TV appearance presented a slight logistical issue. Call time was painfully early, hair and make-up aren’t provided at the studio and I needed enough space to get camera-ready without waking two children while also accommodating what felt like half the childrenswear departments of Chicago.
Enter the Four Seasons Chicago. We stayed for two nights, which somehow turned into two completely different holidays. The first night, my husband James joined me sans kids, meaning for approximately 24 hours we could make plans that didn’t revolve around getting anyone into bed at a reasonable time.
We started with lunch at NAIA, a new Mediterranean restaurant on the river with circular waterfront booths and a dock-and-dine set-up where you can arrive by boat (very Chicago summer). We started with spicy margaritas and their tableside hummus, which is made right in front of you and did not disappoint. Then a spritz cart rolled past. Obviously, we needed a second cocktail. The food is overseen by Top Chef Greece winner Athinagoras Kostakos, and we essentially ordered a smorgasbord: spicy feta, saganaki, Lebanese vegetable salad and crispy potato fritters with French onion dip. The potato fritters. OMG.
From there, we walked along the Chicago Riverwalk, which is probably one of my favourite additions to the city. It stretches for more than a mile along the river and is full of cafés, bars, public art and places to sit by the water. There are plenty of places to choose from, but I somehow always end up back at City Winery for its wines on tap and gorgeous garden set-up. Island Party Hut is fun if you’re in the mood for something a little tiki, Tiny Tapp often has live music, and The Northman Beer & Cider Garden has a casual European beer-garden feel that makes my British husband feel right at home.
Eventually, we made our way back to the hotel to check in. One thing I immediately loved about Four Seasons Chicago was the flow of the main floor. The lobby sort of rolls into the coffee bar, which rolls into the lounge, which rolls into the bar and then the restaurant. There’s an old-world glamour to it without it feeling stuffy. A little Roaring Twenties opulence mixed with something much more modern. Naturally, we headed straight to the bar.
After chatting with the bartender, we learned that the signature cocktails had been developed with Mexican mixologist Olimpia Calderón Ibarra, who comes from Mexico City’s Handshake Speakeasy, named the World’s Best Bar in 2024. I opted for the Ratatouille Margarita: tequila with tomato and yellow bell pepper cordial and habanero tincture. I appreciate that I may have lost some of you at “tomato,” but trust me on this one. It was unlike any margarita I’ve had before, in a very good way.
From there, we moved to our table at Adorn. I had already read that there were house pretzels with pimento cheese on the menu, so frankly, I was sold before we sat down.
A quick pimento cheese PSA for anyone outside America: why have we not successfully exported this yet? In the UK, Homewrecker is one of the only brands I’ve found making anything remotely similar and it can be nearly impossible to find. So when I see pimento cheese on a menu, I order it. Back to the pretzels. Excellent.
We also ordered the housemade hummus, which James declared was “the best hummus he’s ever had.” A bold statement considering we’d eaten hummus at lunch approximately eight hours earlier where he exclaimed a nearly identical statement, but there we are.
Our sommelier, Anna, then talked us through the wine list based on what we were ordering. I loved this because she didn’t just point us towards the obvious choices; she got us trying things we probably wouldn’t have ordered ourselves. We were heading to Napa Valley a few weeks later, so I also felt like I was getting a mini wine lesson ahead of the trip. James had the filet with truffle pomme purée, I had the rigatoni al pomodoro and we split the Caesar salad. The following morning, we decided to really milk the final hours of being child-free and booked ourselves into the spa.
We spent some time in the sauna and steam room before our treatments, and I had the signature facial using some of my favourite skincare brands, including Irene Forte and Omorovicza. I emerged suitably glowy and hydrated for television the following morning, which was lucky because sleep was about to become slightly less plentiful. James left to play golf while I ran around the city doing last-minute errands for the fashion show.
This was also when the hotel’s location on Chicago’s Magnificent Mile became extremely useful. If you’ve ever had to find one very specific accessory hours before live television, you’ll understand that being surrounded by shops is basically a wellness amenity. Then my mum arrived with the kids. And our sophisticated little adults-only Chicago stay was officially over.
One reason I’m such a fan of Four Seasons hotels is that they manage to be genuinely child-friendly without suddenly making the experience feel any less luxurious for the adults.
My children, incidentally, have become very accustomed to child-sized hotel bathrobes and slippers and now seem personally offended when a hotel doesn’t provide them. Four Seasons also does all the little things brilliantly: treats waiting for them, cuddly toys to take home and those small touches that make children feel like the hotel is excited to see them, rather than merely tolerating the fact that their parents brought them along.
Within approximately seven minutes, mine wanted to see the pool. And this particular pool comes with a brilliant bit of Chicago trivia. The pool scene in Home Alone 2, where Kevin asks if he can practice his cannonballs, was filmed here. Gosh, I love that movie.
So naturally the children basically recreated the scene while my mum and I sat in the hot tub. Everyone contributed according to their skill set. Little did they know I had another surprise waiting upstairs.
I had arranged for an old-fashioned ice cream cart to come to the suite so they could make their own sundaes. When the trolley rolled through the door covered in ice cream and what appeared to be every topping known to an eight-year-old, their faces were priceless. There are the luxury hotel moments adults remember… a brilliant cocktail, a facial, an amazing view and then there are the things your children will probably still be talking about two summers later. This was definitely the latter.
Dinner that night was another Chicago essential: Lou Malnati’s deep-dish pizza. It’s my all-time favorite and, when you’re feeding children and grandparents while simultaneously preparing an entire fashion segment for the next morning, ordering pizza to the room isn’t giving up. It’s being sensible. We put the kids to bed, steamed all the fashion show outfits and attempted an early night. Attempted being the operative word.
The hotel starts on the 30th floor of 900 North Michigan Avenue, so the views are pretty spectacular. We were lucky enough to be staying in a corner terrace suite overlooking Lake Michigan and the city.
At some point in the early hours, I woke up and couldn’t get back to sleep. My brain had started doing that incredibly helpful thing where it runs through everything that could possibly go wrong the following morning. So I watched the sun come up over Chicago and, inevitably, started thinking about Homecoming again.
There’s a part of the song about leaving Chicago to follow your dream, and about representing the city and wanting to make it proud. That hits a little differently when you’re standing thirty-something floors above the place you grew up, surrounded by racks of clothes for a fashion segment you’re about to present, while your London-born children are asleep in the next room.
My career took me away from Chicago. First New York, then London which is where I now call home. But I suppose leaving somewhere doesn’t necessarily make it any less yours.
Eventually, the rest of the suite started to wake up. Because I knew my sunrise moment would quickly be replaced by the specific chaos that comes with live television, I had ordered breakfast to the room.
There is something wonderfully indulgent about waking up in a hotel and having breakfast arrive at your door. No getting dressed first. No trying to convince a child that a well-rounded breakfast doesn’t mean a pain au chocolate. Just open the door and in rolls pancakes, eggs, coffee, juice and most importantly the French toast.
The French toast. I don’t know what they do to it and frankly I don’t need to. I just know it lives rent free in my mind to this day.
Actually, this is what I mean when I talk about luxury being the things you don’t have to think about. On a morning when my brain was already occupied with models, outfits, call times and whether I had remembered absolutely everything, breakfast simply appeared. Everyone was happy. Everyone was fed. I had coffee. Luxury.
Of course I appreciate the beautiful suite, the spa and a very good margarita. I’m not going to pretend otherwise. But these days, luxury is often less about what gets added and more about what gets taken off my plate. For those 48 hours, I didn’t have to think about everything else.
There was enough room for hair and make-up to arrive while the kids slept. Someone could wheel an ice cream trolley upstairs and make their entire afternoon. My mum and I could sit in the hot tub while they practised cannonballs. James and I managed a proper dinner and a morning at the spa. And somewhere amongst live TV, racks of clothes, two children and emergency jean surgery, I actually got to enjoy being home.
Sometimes the most luxurious thing a hotel can give you isn’t another thing at all. It’s the feeling that somebody else has got it.
After the usual whirlwind of live TV, clothes, children, cues, outfit changes and trying to remember what I’m actually supposed to be saying while also making sure everyone’s trousers remain firmly where they’re meant to, I was genuinely sad to leave our little home in the city.
In 48 hours we’d somehow managed date night, cocktails, a spa morning, family time, cannonballs, deep-dish pizza, an ice cream trolley, a sunrise and a live fashion show. A little glamorous, a little chaotic and slightly exhausting. So, basically, my life.
And maybe that’s why Homecoming still gets me. Kanye may have been singing about a girl called Windy, but we all know who he really meant. Chicago, I do think about you now and then.Because I’m always coming home again.
