• Revellers

Windy City Wonder: 48 Hours in Chicago


chicago bean cloud gate in the snow

Like the lunatic that I am, I decided to jump on a long-haul flight in early January and head to one of the most notoriously inhospitable US cities in winter. Cries of "In January?!" and "Good luck" echoed around me. But I had good cause.

An American Opening Night.

Back in Autumn last year my brother, theatre director extraordinaire Simon Evans, got the great news that a show of his had transferred to Chicago's Goodman Theatre. This marked the first of his work to move across the pond and I was not going to miss the opportunity to support him.* Having never visited the Windy city, I was determined to cover as much of it as possible in the brief weekend that I had there, and I think I had damn well. So, you're most welcome - here is my guide to 48 perfect hours in Chicago.

*Experience a press night in Chicagee.


I landed late afternoon, and after a somewhat laborious customs queue (thanks closed government) I made it out of the airport.

❄️Getting from the Airport❄️

The cheapest way to get from O'Hare airport to downtown Chicago is on the good old "L train" (short for elevated train because it soars above the city for the most part) and I'm a lover of immersing myself in local habits whilst in a foreign city, so public transport felt like a good start. It was super easy, and got me within a few blocks of my hotel for $5. And boy did I fall hard in that first short walk.

Chicago at night neon sign




Somebody said, "it's like a quieter and cleaner New York" and I get that. There was something oddly peaceful about it despite the towering sky-scrapers, and the first moment that I walked out into the surprising openness of the river bank, I was floored. It is totally stunning and unexpected to suddenly encounter so much sky in the middle of such a bustling city.

chicago river at night skyscrapers

❄️Dinner in Chicago - Pizzaria Uno❄️

pizzeria uno chicago neon sign

Having reunited with my brother, we headed straight out for dinner: deep dish pizza, right off the bat. Luckily for us, our hotel was just a few minutes away from Pizzaria Uno, apparently the original creators of the Chicago Deep Dish pizza. And it did not disappoint. I can't recommend this highly enough if you're looking for some classic carby goodness. I do wish they wouldn't include the calorie count on the menu though - it's like ordering a Big Mac meal: I know I've made a deal with the devil, I don't need to read the fine print. There was literally one pizza that was topped with fried chicken, 4 different kinds of cheese and had a calorie count of 600-950 per slice, mine and my brother's main question being "where does that range come from!?" But the food was totally delicious, the place was buzzing and the bill was kind!

pizzeria uno deep dish pizza chicago
Pizzeria Uno DeepDish


❄️Big Bus Chicago❄️

big bus chicago snowy day january snow

A few of the crew on Simon's show had already ticked off the Big Bus tour earlier in the week and sold the idea to us. I was previously a bit sceptical of Big Bus; whenever I see them chugging around London they feel like the most uncharacterful, basic-bitch way of seeing an iconic city. But actually, this was terrific. It did an excellent job of giving us an overall glimpse of the whole downtown district. We saw the Sears Tower, the oldest standing buildings from before the great Chicagoan fire of 1871. and we attempted (but failed) to see the skyline through the ever thickening snow and cloud. (Chicago in January, amiright?!) The Big Bus tour will set you back $45 a person, but the full tour lasts about 2 hours and your ticket enables you to hop on and hop off all day. We chose to do the whole thing in one chunk, but there's plenty of opportunity to break it up in whatever way suits you.

❄️The Bean❄️

chicago bean cloud gate snow and smiling lady

What did people do in Chicago before The Bean?? Now the most iconic tourist hot-spot of this lakeside city, its instagram potential only quadrupled thanks to the snow storm we found ourselves in. Cloud Gate (its official name, dontcha know) sits right in the corner of Millennium Park, which I have no doubt we would have spent more in had the season been more hospitable. As it was, we were dealing with horizontal snow and temperatures of -5C, and we actually had to duck into the Cultural Centre over the road a couple of times just to thaw our hands (memo to reader: the Cultural Centre was not worth visiting for any other reason; it was a strange, beautiful building but that seemed to have no idea what its purpose was).

❄️The Chicago Art Institute❄️

a sunday on la grande jatte in chicago art institute while a man and children look on

Forgive me for being such a heathen, but I'm not massively into art. *Cue Freddie walking over to my desk and giving me a firm slap across the face.* Of all the cultural delicacies on offer in this world, it's the one I am most uneducated on and that gives me the least pleasure. That being said, the Art Institute was raved about to me by so many people that I'd have been an idiot not to go! And it certainly lived up to the hype: an enormous, beautifully structured collection of

buildings with plenty of my fave: Monet. I remember seeing a relatively unknown Monet in the Guggenheim last year and it totally silenced. The colours were almost other-worldly (or rather they were absolutely this-worldly, but this-worldly-at-its-earthly-best) and I've been a passionate fan ever since. There was plenty of Monet in the Chicago Art Institute. There was also Georges Seurat’s A Sunday on La Grande Jatte, and there was the also "the Miniature Rooms", which is a must-see if you go there. I'll say no more about them, just go...

snowy view from chicago art institute industrial beam

❄️Dinner in Chicago - Demera❄️

demera ethiopian food and man

This was a recommendation from a friend of my brother's. He and his wife claimed it was one of the best meals of their life so, even though Ethiopian cuisine is not what you'd naturally expect to chow down on in Chicago, it was worth a visit! I have to say my favourite thing about the whole experience was the lack of cutlery. We had a delicious platter of vegetarian food in which we could sample all the best dishes on the menu, and every single one was to be scooped up in Ethiopian bread or picked up with your fingers. We had a really jolly meal and stocked up on some much-needed fibre at the same time!

❄️Green Mill Jazz❄️

green mill jazz bar chicago band playing

Right across the road from Demera (it's almost as if we planned it) was Green Mill Jazz Lounge, a live music bar with a fabulous history. Apparently this was Al Capone's favourite joint in town and it even has a set of underground tunnels he used as a hasty escape route when the cops burst in. Apparently there was also a strict rule in place that whenever Capone arrived, the bandleader had to stop whatever they were playing and dive right into Rhapsody in Blue...! There was no Rhapsody in Blue played the night we were there, but there sure as hell was some fantastic music. It cost $15 entrance fee and much to my brother and my relief (eager for a dry night), there was no pressure to order drinks when you were in there. That being said, the cocktail looked insanely tasty and I'm a little ashamed we didn't have one. This is an absolute tip-top recommendation. Jet-lag was defeating me on this particular night, but next time I return to Chicago I'll be planning a big night here.

green mill cockatil lounge jazz bar chicago outside


❄️The Beach❄️

Yesterday's snow storm had totally cleared and left a crisp bright morning, perfect for a little amble along the beach! I've never seen a beach covered in snow, but there's a first time for everything. It was incredibly peaceful on Oak Street Beach (we were the only ones crazy enough to be there) and offered some gorgeous views along the lake and back at the towering skyline.

chicago beach in the snow john hancock centre

❄️875 North Michigan Ave (John Hancock Building)❄️

view from signature lounge in john hancock centre north 875 michigan avenue

And talking of towering skyline...! There's a great debate in Chicago concerning which skyscraper is the best to haul yourself up. In New York it's a no brainer (Top of the Rock every time. If you queue for the Empire State you're a fool), but in Chicagee the race is a little closer. Do you pick the Ledge feature of the Sears' Tower Sky Deck, or the Tilt experience at the John Hancock Building? Well, we did neither! Little money-saving tip coming up: If you'd rather put your dollars into a morning coffee or a sundowner, skip the ticketed observation areas altogether and head to the John Hancock Building's Signature Lounge. 96 floors up (that's one higher than the official viewing deck) there's a restaurant and bar that opens at 10am (11am on Sundays). Cocktails are $17-18 and a cup of tea will set you back $6 (without tax and tip), but you can just sit back and relax and properly soak up the view. Simon and I spent about an hour sat up here, sipping hot drinks, reading our books, intermittently getting up to take another picture or check out the view from the other side of the lounge. It was a really lovely way to see the skyline.

❄️Brunch in Chicago - Dove's❄️

girl with brunch at dove's chicago smiling

This is a bold claim but I think I had one of the best platefuls of food ever here. For weekend brunch there was a 30 minute wait when we arrived, but no sweat: Dove's is just round the corner from Myopic Books, an irresistible second-hand book store that you could lose a good few hours in. Once our table was ready, we nestled in between other brunchers on the long banquet table we were all sharing and perused the menu. I was torn between a number of the saliva-inducing Tex-Mex dishes, but my eye kept being drawn back to the Tofu Toast. I'm not usually a tofu fan but everything else about it sounded great and after hearing the waitress recommend it as her favourite, I made my decision. Reading the menu description, looking at a picture, none of this will do the dish justice. There were apples, there was butternut squash, there was toast, but also there simply must have been fairy dust and unicorn tears because the plateful was out. of. this. motherclucking. world.

tofu toast dove's chicago butternut squash and greens

❄️The 606❄️

north chicago road

It's not quite the Highline, but it's very pleasant. In warmer weather or with more time, I could happily have wiled away a couple of hours sauntering along this elevated walkway. As it was, Simon and I just walked from the Churchill Field ramp to the Western station ramp, but it was delightul. Definitely worth a wander if you're in that part of town.

the 606 in chicago in the snow

❄️Theatre at the Goodman❄️

goodman theatre neon lights chicago

And finally we come to the trip's heart, the filling of the doughnut, the meat to the pie: My brother's press night. Simon had directed the incomparable Brendan Coyle in Conor McPherson's St Nicholas for the Donmar Warehouse in London; it had since gone to Dublin and was now in the windy city, before transferring to NYC in the summer. It is an utterly unique and deeply moving one-man story about an alcoholic theatre critic who gets kidnapped by vampires. Yeah. Fabulous. Brendan captures your attention and holds you relentlessly from his opening "When I was a boy..." to his final heartfelt plea and I could not love this production more. The opening night was a triumph. My brother was happy, the creative team were happy, the Goodman Theatre staff were happy, it was a happy occasion. We all headed to Tortoise after for champagne and canapés (and prawns and burger for Brendan and Simon who decided together that canapés were not sufficient) and then stumbled home to our beds.

cast and crew of donmar warehouse st nicholas in chicago goodman theatre

❄️We stayed:

My brother and I were staying at Homewood Suites by Hilton in their Downtown location. The room was spacious and homely, although I won't recommend the sofa bed in a hurry. It was perfect for a short city break though. Incredibly central, allowing us to walk to and from nearly every major tourist hot-spot, and the free hot breakfast was a bonus.

❄️Getting round:

The L train is super easy to use and cheap ($2.50/$3.00 per trip) but uber was also great.

❄️Other recommendations that I didn't have time for:

Steppenwolf and Looking Glass Theatre

Second City improv

Sears Tower (Willis Tower)

Architectural boat tour (Out of season in January) Gangster bus tours

under the l train chicago

girl stands beside caution falling ice sign looking up worried

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