Postcards | Chicago

This early #MattTheTrips adventure was way back in 2014 and I haven’t been back since BUT I keep an eye on Eater & Thrillist, and I have some spies in the field. Hopefully I’ll make it back before too long to top it up. Our week in Chicago came after seven days in New York and a few more in Toronto, so food fatigue did start to creep in towards the end, but we put in a good shift, not least our hosts Emma, James & Miranda who made it to around thirty places themselves whilst holding down jobs, and Tim who ridiculously flew to the UK and back for a wedding for twenty hours midweek. Insane.

You may have missed Hot Doug’s, but there’s plenty of fun to be had elsewhere.  Deep Dish Pizza isn’t essential, but I know you are going to eat some anyway – Lou Malnati’sGiordano’s and Pizano’s have you covered.  The brunch scene isn’t half bad – Longman & EagleAvec & Trenchermen come highly recommended, and the meaty Publican is excellent – ask to sit in one of their cosy pens to feel like even more of a piggy. Pick up some treats at Glazed & Infused afterwards to seal the deal.

Down the road from Publican you can find two of Chicago’s most talked about hotspotsGrant Achatz & Nick Kokonas’ exclusive high-concept Next Restaurant (also see Alinea), and their acclaimed cocktail bar The Aviary (with award-winning Charles Joly heavily involved).  If you ask nicely, they might let you in to The Office, an underground speakeasy kept under lock and key. We managed to pay it a visit and had a great time, though the bartenders don’t quite pull off the forced whimsy.  The menu is a series of sentences that are intended to inspire discussion and aid them in making a personal drink for each customer.  It’s a unique experience at any rate!


You are spoilt for choice around the West Randolph area with the likes of Little Goat, Girl & The Goat, Lone Wolf and Au Cheval, but if you love meat and fairy lights like me then you must go to Green Street Smoked Meats (pictured below).  Think New York’s Fette Sau on a grand scale crossed with Street Feast’s Dalston Yard.  Plus there’s High Five Ramen hidden in the basement, and a Doughnut Vault van parked up outside (at least when I was there!).  Speaking of doughnuts, be sure to drop in to Firecakes for a box – delicious. Wash down with Bowtruss or Intelligentsia coffee. Oh and if you want more fairy lights and meat, Parson’s Chicken & Fish was another highlight (extra points for Negroni slushies) and Big Star is a colourful taco station.

Get an Uber over to Pilsen so that you can tick off knowingly cool Dusek’s Board & Beer and Punch House ($8 cocktails on tap), before dropping in to nutty Simone’s (possibly run by a cult?) and dive bar Skylark.  Once you’ve come that far, you might as well head to Bridgeport for Maria’s Packaged Goods & Community Bar – a lively bar attached to the eponymous Maria’s liquor store with in-house brewed beers, cocktails & more.

What else? Oh yes, BEER.  Half Acre was our favourite taproom, with Revolution & Piece close behind, though popular Local Option eluded us.  Our favourite beer bars were the travel-centric Map Room, motorcycle-themed Twisted Spoke, gamer’s paradise Emporium (the enormous one near Logan’s Square specifically), and the Fountainhead rooftop garden.  We sadly missed out on Hop LeafBeermiscuous and Headquarters Beercade – next time! Beer geeks should also make time for a jaunt over the border to Indiana for the Three Floyds brewpub. Plenty more has opened since our trip too, so check out Eater & Thrillist Chicago for the latest tips.

My favourite cocktail bar was neighbourhood hangout Billy Sunday on account of the welcoming vibe, funky menu and knockout drinks.  Elsewhere, Three Dots & A Dash is Tiki done well; The Violet Hour is a speakeasy with top libations but questionable décor; and Scofflaw is all about the gin.  I’ve already mentioned a couple of dive bars, but be sure to pop in to Happy Village for table tennis and a pond (!), and to the ultra thin Matchbox.  If Chicago has another insane Winter, these are the places you need to know about.

Any last words? Honey Butter Fried Chicken. Table, Donkey & Stick. Par King Skill Golf.

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