Wandering the Windy City – Chicago in 4 days

Chicago, IL

I’ve been Jonesing to get back to Chicago since 2013 – when we were there last. It feels like a lifetime ago.

Finally, we’ve managed to organise ourselves enough to get back to the Windy City and I’m seriously excited. Last time we were here, Christina was at a conference, leaving me to my own devices. 

This time, we’re together the whole time, which means I can finally show her some of the things I saw plus explore the city a bit more thoroughly. 

We only have four days in this incredible city, but I think we manage to fit in a pretty good amount. I think we’d be able to do more if we weren’t so weighed down by our own gluttony – a gluttony (almost) sated by the incredible barbecue things happening in Kansas City, our previous port of call.

But here we go: Chi Town as seen by Mr & Mrs Romance!

Cheers – Jim & Christina xx

Chicago, IL

From Kansas City, we’ve climbed aboard a Southwest Airlines plane and learned there’s a whole new way of boarding a flight! If you haven’t heard of this before, look it up – Southwest do it differently!

They also give you not one but two free checked bags – a thing unheard of in the USA. And not only that but their in-flight service is excellent too.

Anyway, as we come in to land at Chicago’s Midway Airport (way nicer and closer to the city than O’Hare by the way), I get that tingle of excitement I always feel when I’m excited about a destination… or it could be the margaritas we’ve just had.

Yes, we did!

Kimpton Hotel The Gray, Chicago, IL

Our first stop – obviously – is to our hotel. We’re staying in the beautiful Kimpton Gray Hotel right in the city. 

We unpack and examine our room, which is – like the rest of the hotel – fun, yet sophisticated, young, yet in keeping with the classic aesthetic of the building. It’s a difficult balance, but they’ve nailed it here. 

We head downstairs to dinner at the hotel’s restaurant Steadfast, where I feel duty-bound to try their wagyu, which is exceptional. Christina’s salmon looks superb too (she doesn’t let me try any!) and our friend Ann’s pork shank is enormous. 

For such a food-centric city, Steadfast holds its own and clearly operates independently of the hotel.

Kimpton Hotel The Gray, Chicago, IL

The Gray truly is a stunning building. It was in fact the first skyscraper to go up after the 1871 fire. Like I said, the aesthetic to this place is wonderful; grand, luxurious and stylish. 

We’ll have a full review of this coming, don’t worry. In the meantime, if you’re heading to Chicago, we’d recommend this hotel for certain.

The Bean/Cloud Gate, Chicago, IL

This morning, we’re out and about checking out the sights. Of course we had to come here to see The Bean – or as I’m sure its creator artist Sir Anish Kapoor would prefer ‘Cloud Gate’.

It’s such an unusual, iconic sculpture. In fact, it’s more of a monument.

Art Institute of Chicago, Chicago, IL

While we’re feeling arty, we head to the Art Institute of Chicago next. This is a truly enormous facility and could easily take up a whole day if you wanted. 

Sadly, we don’t have the luxury of a whole day to spare, but we do our best!

Georges Seurat, Art Institute of Chicago, Chicago, IL

Far from just being a gallery, the Art Institute of Chicago is a museum, an education facility and a keep of treasures. 

There are pieces from all over the world from all times here. Ancient Greek and Roman artefacts, even Etruscan. And the Asian collection is kind of mind-blowing. They have things here from the 12th Century BCE. 

Probably my favourite part of the Art Institute though is the impressionism section. They have an enormous Monet collection and even have this classic – A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. Amazing.

Chicago Cultural Center, Chicago, IL

For one last drop of culture, we find our way to the Chicago Cultural Center. This building really needs to be seen first-hand. For starters, everything you see in this photo that’s coloured is made of glass mosaic. It’s insanely beautiful.

Chicago Cultural Center, Chicago, IL

Chicago Cultural Center, Chicago, IL

There are some fascinating installations throughout the centre, but it’s really the building itself that’s captivated us. At times the staircases are like something from an Escher drawing.

Bar Biscay, Chicago, IL

This evening, we’re at Bar Biscay, a belter of a restaurant that seems to punch way above its weight from what we’ve seen. 

We’re here as part of a group to explore the wonders of rare natural French wines brought to us by Pierre Gastaldello from Bobo Wines. It’s interesting to hear him talk about the challenges and respective rewards from buying, drinking and enjoying wine that’s made by small producers who don’t add anything but the grapes to their wines. 

The wines are paired intelligently with superb food by Bar Biscay’s own head chef Johnny Anderes, who’s created an impressive degustation menu to champion each varietal.

Bar Biscay and Lagniappe collab, Chicago, IL

One of the wines we try tonight is this wonderful Cabernet Franc by Nicholas Reau. He designed the label to mimic a parking ticket he saw in his hometown in France – it’s a notice your car’s about to be towed but translates nicely to demand you take the wine.

Beautifully made, this wine goes exquisitely with the slow-cooked leg of lamb and olive tapenade Chef Johnny has made.

Bar Biscay, Chicago, IL

After dinner, owners Scott and Sari sit with us at their excellent bar and chat over a couple of drinks. 

Scott’s full of great yarns including a story of how he met Benicio Del Toro in Puerto Rico, hid him from crazed fans, took him to a bar next door.

Over a couple of beers, Scott explained what a fan he was of Hunter S Thompson – it was around the time of The Rum Diary – and Del Toro offered to call Thomson for Scott to chat to. It would have been about 3am.

Scott said no and laments saying so to this day, but I think his whole story is a pretty Hunter S Thomson tale anyway. No regrets, buddy.

The Kimpton Hotel Monaco, Chicago, IL

This morning, we’ve moved hotels! Still in the warm caress of Kimpton, we’re now in The Monaco, right on the river. And this time, we’re in a suite. Not just a suite, but a penthouse suite. 

Not bad, ay?

Of course, there will be a full review coming up of this marvellous hotel too, but I don’t think it needs to be pointed out how amazing this place is. The view is incredible, the room is vast and spectacular, and the hotel itself is full of the lovely details that make Kimpton hotels such an easy choice when you’re travelling.

Chicago bridges lifting, Chicago, IL

As we gaze out the window at our view, Christina notices the bridges along the Chicago River are lifting. 

We don’t know how common an occurrence this is, but all the bridges along the river are going up to let a fleet of sailing yachts through. The congestion it must be causing through the city makes us glad we’re up here looking down, but being able to watch it all happen is quite extraordinary.

Kimpton Hotel Monaco, Chicago, IL

It’s the little touches that really take a hotel from being just a comfortable place to sleep to somewhere you’re sad to be checking out of at the end of your stay. The Kimpton Monaco Chicago is certainly one of those. 

The attention to detail – just in our room – is amazing. Art on the walls, interesting furnishings, pretty decorations and USB ports everywhere… I really don’t want to leave this room. 

Chicago, IL

Chicago, IL

Chicago, IL

Finally we take to the streets to see more of the town. It’s getting chilly here in Chicago, but every now and again the sun will pop out and warm us up.

Walking down by the river and across the bridges around the Magnificent Mile, I could very easily get used to this city.

Shydeck Willis Tower, Chicago, IL

We’ve made our way to the Willis Tower – what was once the tallest building the world. Views from up here are, as you’d expect, extraordinary.

It’s well worth coming here to see out over the city, the lake and – in fact – across three states. It’s $45pp to come up here, but we have Chicago City Passes, which are around $100 each. Kind of almost pays for itself already.

The ticket up here includes a second visit in the evening to see the city lights, but also a host of other attractions that, if you’re in town for a while, will really save you money.

Access to the Shedd Aquarium, the Field Museum, Adler Planetarium, the Art Institute of Chicago, which we’ve also used, the beautiful Museum of Science and Industry, which is in one of the last remaining buildings from the Chicago World’s Fair that saw the advent of the Ferris Wheel, and the 360 Chicago Observation Deck in the Hancock Tower. 

Shydeck Willis Tower, Chicago, IL

The Willis Tower’s Skydeck and Ledge is a little unnerving, but an amazing experience. You’re literally hanging out over the edge of this 442m skyscraper with nothing stopping you from dropping than a sheet of glass. Look how happy Christina is.

Shydeck Willis Tower, Chicago, IL

After all my barbecue escapades, I’m not feeling as confident as Christina, but I’m the only one on the glass here and I’ve just seen a whole family jump up and down on the glass. I should be fine!

Chicago, IL

We walk the streets of Chicago until our feet are sore and we know it’s time for bed. It’s such a great city – even Madonna thinks so!

We don’t have tickets to the Chicago Theatre, so instead I take Christina to one of my other favourite music spots: the Redhead Piano Bar. It’s a classic where a guy plays the piano and everyone sings along. It’s like being at the the drunk un-aired end of an episode of Cheers. It’s amazing. 

Navy Pier Ferris Wheel, Chicago, IL

It’s only right that we take a quick walk to Navy Pier. It’s an icon of Chicago and the Ferris Wheel (not the original from the World’s Fair – that one got sent away south and fell apart at the turn of the 20th Century) turns slowly creating an amazing backdrop to the city.

Now, hang on, I hear you say. What about all the food and drink you guys usually love talking about? So far, you’ve only talked with any detail about one place.

Well, brace yourself. Here we go…

Lou Malnuti's Deepdish Pizza, Chicago, IL

At a certain point, we had to do it. Last time we were in Chicago, we tried Giordano’s for a deep dish pizza. This time, we’re at Lou Malnati’s and I think we have a winner. 

There are a number of places around the city doing this style of pizza – with a crusty base, a thick layer of cheese topped with chunky tomato sauce and Italian sausage, but sadly we don’t have time to see more. 

It seems also that Giordano’s does a filled pizza, with an extra layer of pizza dough base between the cheese and the tomato, which some think of as cheating.

Whatever. Lou’s is a good pizza.

Portilllo's hotdogs, Chicago, IL

We also try another Chicago cuisine at another institution: The Chicago hotdog at Portillo’s. These dogs are full of stuff you wouldn’t get in other cities. The giant pickle you see is one!

Would I recommend a Portillo’s dog? Absolutely!

While we’re at the whole food institution thing, Christina and I also hit the Billy Goat Tavern for a cheeseburger… or should I say ‘cheezborger’.

It’s a place that was lampooned and sent to fame in a Saturday Night Live skit when the likes of Dan Aykroyd and Bill Murray were still there. Check out the skit here.

The cheeseburgers are definitely worth seeking this place out. Absolutely delicious. I think we’ll be talking more about both Portillo’s and the Billy Goat again soon too!

Revolution Brewing Co, Logan Square, Chicago, IL

This afternoon, we’ve taken the train out to the villages north of the city. Here at Logan Square, which used to be a real dump from what a local was saying, the bars, restaurants, breweries and distilleries are popping up everywhere. 

Indeed, our time at the impressive Revolution Brewing on North Milwaukee Avenue is the best. We sit at the bar and Steven, who’s pouring brews, is a deadset legend. 

We try so many of the brewery’s beers including the flabbergasting Cafe Deth – a black porter blended with a local coffee roaster’s beans to make a thick, unctuous brew that’s both caffeinated and 14.8% – an interesting blend and way better than any espresso martini you’ll find.

Chicago Distillery, Chicago, IL

Our next stop, just a little up the road, is the equally impressive Chicago Distilling Company. We get chatting to Aaron behind the jump and learn a bit about the distillery. 

They make plenty of white spirits – in particular a lovely gin. But they’ve also started selling their aged whiskey too now, which is exciting. Aaron gives us a taste of the single malt they’re doing – wow! Amazing.

They also make a superb rye called the Blind Tiger, which I had to buy a bottle of – especially at the price of $54. Magic.

We pop into a very cool, cosy bar on the way along called Scofflaw. Highly recommended – they also stock Chicago Distilling’s Flinn’s Gin. Of which we have a (huge) martini each. Hic!

Scofflaw speakeasy, Chicago, IL

After a bit of a walk, we stop in at Best Intentions – a cool little hipster divebar with good drinks and original arcade games out the back and a very cool looking beer garden. If only it were warmer.

We pull up at the bar after a couple of rounds of Buck Hunter and Calvin the owner talks to us about why he has Angostura Bitters on tap. After a shot, I see why. It’s actually amazing! He goes through five gallons a month!  

Cafe Marie-Jeanne, Chicago, IL

Next, it’s time to walk off some of the booze. We hike right across Humbolt Park to a crossroads with food and drink on all four corners. First we hit Cafe Marie-Jeanne for a beer, a plate of steak tartare (my weakness) and a meat and cheese plate. 

The tartare is good – a little chunky – but well seasoned, but the cheese is amazing.

The cheese is a delice and ‘Good Thunder’ – a creamy brie style and a lovely stinky washed rind. There’s plenty of sliced coppa on the plate but for the price I’m not so sure the cheese is worth it. Or maybe it is. I don’t know.

Burger at Rootstock, Chicago, IL

Finally, we head across the ‘kitty corner’ diagonally to Rootstock. It looks kind of filthy on the outside in a way that would probably stop germaphobes at the door, but inside is clean, warm and comfortable. 

We pull up at our favourite spot: at the bar.

Until this point, everywhere we’ve been the whole time we’ve been in Chicago, people have been so friendly. Sadly, our run ends here with a real asshole behind the bar.

We were ‘graced’ with the presence of co-owner Johnny Hap, who seems to think he has the personality to carry off being confrontational with customers and doesn’t realise he’s coming across as simply rude. Or maybe he does and doesn’t give a toss. 

It’s a real shame because the people we meet on our side of the bar are amazing; friendly, fun, great company. Even more of a shame is that the wine list is excellent here (I try and strike up conversation with Johnny about a particular wine on the list and why it’s there. He explained it was what the supplier gave him) and the food is annoyingly good.

This burger should probably win an award somewhere. I’m serious.

Meat-focused, perfectly seasoned, charred outside and cooked to order. It’s really worth the journey. Just roll those dice on who’s working the bar when you’re there!

Skydeck Willis Tower and us, Chicago, IL

It’s been an amazing time here in Chicago and if anything, it’s just made me want to come back again sooner.

We hope you’ve enjoyed this Edition.

Cheers – Jim & Christina xx

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