Taking full advantage of having in laws staying, Hutch and I escaped to Chicago for a mini break sans kids. It’s the first time he’s had away from them since we got to the US, I’ve disappeared a couple of times to NYC, but no real time out together in over a year. It was a toss up between Chicago and Montreal. I was keen on Canada, but Hutch had googled Michelin star restaurants and there are plenty in Chicago. Flights were cheap, we used Expedia and paid $380 return for both of us, and we found a lovely studio on Air b’n’b that was a steal! I left it to Hutch to plan the restaurants but vetoed Alinea, three stars it may be, but way too expensive.

We checked in online on Thursday night and the website said there was a possibility that the flight was overbooked and would we be interested in volunteering to take a later flight, compensation would be provided? I figured that we weren’t in a hurry, and that there were probably other people who needed to get to Chicago quicker than we did. When we got to the airport we were bumped, given hundreds of dollars in compo vouchers and access to the United lounge. Happy days! Hutch got to watch a replay of the Bombers game against the Hawks, and we ended up leaving at 930.


Dinner on Friday night was at Sixteen on the 16th floor of the Trump Tower and Hotel. It’s got 2 Michelin stars and is fancy. Lots and lots of waiting staff, a set nine course menu with two themes; Day or Night. The day menu focusses on the springtime, new growth and fresh flavours, the night menu focusses on things that grow without light, and has more of a seafood bent. We chose the Day menu, and it was very entertaining.


My favourite flavoured courses were the first, ‘The Rising Sun’ was cured salmon, kumquat, haricot vert, lemongrass chantilly and osetra caviar, and the last ‘May Flowers’ huckleberry filled goat cheese mousse, with almond financier and mountain mint ice cream.

The most entertaining was ‘Melting Snow’ which involved a mushroom tea being brought to our table, heated with a small gas flame and the liquid was sucked into a top chamber to be flavoured by nasturtium and other greenery. On cooling it flowed back into the bottom chamber and was then poured over a hollow ball of ice, symbolising the melting snow. It was amazing from a drama point of view, but unfortunately because the hot tea was poured over the cold ice, actually meant the meal was tepid and probably my least favourite taste.

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The view from the 16th floor of the Trump Tower feels as though you aren’t very high within the skyscrapers of Chicago, a great view of the Wrigley building (of chewing gum fame) that has now been taken over by Groupon. Here’s before and after sunset.

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The architecture of Chicago is very interesting, it feels like a really old city, the train system is wooden and badly maintained, and the buildings are a mix of old and new. The great Chicago fire back in the 1870s wiped out over 60% of the CBD so there isn’t much left from before that time. There seems to have been lots of building done in the last 20 years and most of them are lovely.

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Saturday we didn’t have a reservation anywhere and after the hammering of the wallet on Friday night, it was probably a good thing. The apartment we were staying in was in Old Town, a few train stops north of the CBD, just near Lincoln Park. We wandered around to the International Museum of Surgical Science and spent an hour or so there, I think I was more keen than Hutch. It had a variety of examples of surgical techniques over the ages, along with some statues of important figures in medical history.

It was freezing on Saturday, about 2 degrees and low visibility. A walk down The Magnificent Mile (also known as North Michigan St) to Eataly for some lunch was about all we could manage. Eataly Chicago is just as good as Eataly NYC, think David Jones Food Hall on steroids, and only focussed on Italian food. We shared a plate of cheese and cured meats and I restrained myself from buying anything.

A short train ride took us to the Art Institute of Chicago. (Just as an aside, the train system is a bit weird, the stations are named for the streets they are on, so there are two Harlem Stations on the Blue line in very different parts of town. There are duplicates on other lines too as well as another Harlem station on the Green line. The city loop runs mostly aboveground on an old system. We quite liked the bus.)

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The Art institute is amazing. If you go, enter from Monroe st, the queues are much shorter and you get straight in to the modern section. We stuck to the art from 1900 onwards and that took us ages. It’s a fantastic collection even with the European section being closed. American Gothic is a great piece, there are lots of Georgia O’Keeffe who I’ve seen in other galleries, but she and her husband Alfred Steiglitz donated quite a bit, so it’s a comprehensive display of their work and collection. A little bit of Warhol, some Pollock, some de Kooning, a lonely Lichtenstein, brilliant. I’d have it in my top galleries in the world.

Saturday night was very low key, dinner in the Old Town and an early night.


On Sunday we woke to a glorious day, well 11 degrees and clear skies, so we were very happy. A mile or so walk through Lincoln Park, past the zoo and up to North Pond, our brunch destination. It’s still very heavy density a few miles north of the business district, the apartment buildings are massive, probably taking advantage of the view of Lake Michigan. We noticed lots of car parking buildings and lots around the city, it seems the public transport isn’t reliable enough for people to commute in by rail or bus. With a population of around 10mil in Chicago and surrounds it’s a big city with some challenges.



After a gorgeous brunch, we caught the bus downtown to join a river and lake cruise. Hutch got fleeced by a shoe shine guy, his lovely brown shoes were polished up nicely, ‘obligation free’ until the end when he was told it was $8 a shoe! I only had a $20 and handed it over way too quickly. After some heated discussion we walked away with $9 change, total rip off.

The river cruise was 90 minutes and the commentator was impressive, she spoke for at least 75 minutes and has a head full of facts and figures. Did you know it’s not called the Sears Tower anymore, it’s the Willis Tower? Naming rights go to the largest tenant. They have also reversed the flow of the Chicago river so the waste water goes down to the Gulf of Mexico. The lock that’s been built to make it all happen has to report to Michigan and Wisconsin every day notifying them of how much water they are taking out of the lake. It seemed quite contentious, a little bit dodgy and a lot of lawyer fees to get approval to change the river. Unfortunately the tap water is fairly gross, very chloriney which seems weird coming from a big lake. The big building in the second photo is Merchandise Mart, so large it used to have its own postcode.

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Off to the Museum of Contemporary Art after that which was much smaller than I expected. It’s supposed to be Chicago’s answer to MOMA but is nowhere near the scale.

Dinner on Sunday night was at Sepia, a one star restaurant than Hutch picked because he liked the website. Again a tasting menu with paired wines, lovely ambiance, dark with big light fittings and brown tones. Fresh flavours with peas featuring, not quite as fancy as Sixteen, but some tasty wine that was very well matched to the food.

Back to the apartment to bed before an early flight back to Boston. A few dramas there, American Airlines won’t let you store more than one boarding pass on your phone so we didn’t have one for Hutch and we arrived as boarding was commencing, a sprint to the gate after pushing to the front of the line at security, and we were allowed on the plane one minute before they drew back the air bridge. Oh and I left my passport in Chicago.

Most cities aren’t at their best at the end of the winter, snow has melted and the springtime isn’t in full bloom. Chicago is an interesting city, one that is great for foodies and with a bit of local knowledge would be a happy place for families too.