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The Chicago Mini City Guide

All the deats from our whistle-stop tour…

This post contains affiliate links (denoted by a ‘*’) & gifted items (denoted by ‘gifted). You can read my full disclaimer here.

*My visit to Chicago was a press trip with Choose Chicago and The Hoxton

My visit to Chicago last month was unsurprisingly class. I say unsurprisingly because everyone who I told about my trip vowed that I would love it, and they were right. It’s a tricky city to describe because it’s so bloody massive that you could spend weeks exploring the suburbs and districts that filter off from the city centre and unless you have that kind of time there then you just have to be cool with the fact that you’re not going to be able to physically visit every single ‘must-visit’ food spot on your list so you’re just going to have to go back at some point. And that’s exactly what I’m going to have to do. So that’s why this is my ‘mini‘ Chicago guide because in the four days that we were there I had just a wee sip and there was so much more to see and do in this place. Need a mental image? Well, if you combine the world-class food scene of New York, with relaxed Toronto vibes then that’s how Chicago felt for me; chilled, creative, casual (and chilly!), I can’t wait to go back one day…

Where To Stay & How To Get Around

Flights from the U.K are pretty frequent and take around 8 hours, which as a nervy flyer I don’t feel is too long and the time difference once you get there is six hours, so once you’ve had a mega sleep on the first night you’ll be feeling fresh in no time at all. We flew via Dublin with Aer Lingus, which meant we did have to take two flights, but it did come with the added bonus of being able to do all the immigration checks at Dublin instead of on the other end, so once you arrive at Chicago you just pick up your bags and you’re done. Nice. I also had two seats to myself on the way there *and* the way back and I’m still not over it.

We stayed at The Hoxton Chicago which I would 100% stay in again. It’s one of their newest hotels, with a stunning lobby and food-offerings that even the locals drop in for. I stayed in a ‘cosy‘ room that had brilliant views over the city and was more than spacious enough for my visit. The bathroom was stunning (and Instagram perfection), and props for the breakfast bag that gets hung on your door each morning. I loved the location too which was slap bang next to some of the best food spots in the city and there were plenty of workout options around too if that’s your bag. I did a Cyclebar class that was two minutes away from the hotel and a Page One Reformer Pilates class that was four minutes around the corner and would recommend both.

Depending on where you’re staying in town a taxi transfer from the airport can take around 45 minutes to an hour (cabs are easy enough to pick up from outside the terminal) and then once you’re there taxis or the subway are your best bet to get around. Of course download the CityMapper app as always which is a godsend when it comes to public transport, but where possible I walked which was a great way to see the city. I’m very sorry to anyone who saw me storming down W Randolph Street piling goldfish crackers into my mouth at rush hour.

Where To Eat

I’ve been a bit scared to write this paragraph as people feel very strongly about food, and rightly so, so feel free to leave me a passive aggressive comment below about how I’ve got it completely wrong. But I feel comfortable in saying that doughnuts and deep dish pizza are the specialties here and I’m all for it. Perhaps the best doughnut I’ve ever eaten was the Chestnut-Glazed Doughnut from Doughnut Vault. Although it’s more well-known for it’s old-fashioned style doughnut (which I did try too!), the gigantic glazed ring was something else (just come early in the morning to avoid disappointment). When it came to deep dish pizza I’d had my expectations lowered by my friends who know of my dislike for melted cheese. Turns out deep dish is pretty heavy on the melted cheese so I was mentally preparing myself for stringy cheese overload, but you know what? It wasn’t too much and I actually quite enjoyed it. I almost toyed with the idea of taking a frozen one home on the plane. We went to Giordano’s which I know is extremely controversial as you either think it’s the best, or the worst and Lou Malnati’s is far superior. Either way you have to give deep dish a go when you’re there, it’s basically the law.

We also ate at Summer House Santa Monica which was great if you fancied some fresh food with California vibes (they have a rosé cart – need I say anymore?), Dusek’s which did a brilliant lunchtime quiche and Longman & Eagle which is just around the corner from the tiki bar, Lost Lake which is a ready-made night-out for you there. Bang Bang Pie was brilliant and now all I want to do is attempt to make pumpkin pie. Then slap bang next to the hotel was Sawada Coffee which came highly recommended and the brand-new Time Out Market which had just opened, which has all the Chicago foodie highlights under one roof.

Other places that came up loads when I asked on Instagram Stories: Au Cheval for one of the best burgers in the city (I missed it in Chicago, but we’re visiting the New York one soon!), although the ones at Billy Goat Tavern are supposed to be good too if a little rougher around the edges, for a fancy meal out loads of you suggested Cherry Circle Room or Bavette’s, Three Dots & A Dash is another popular tiki bar and Publican is another place that’s right by the hotel that’s *the* spot for meat lovers. Also by the hotel are Stephanie Izard’s restaurants which are very, very popular – she won Top Chef over there. Girl & The Goat, Duck Duck Goat and Little Goat Diner all came highly recommended, along with her latest venture Cabra which is actually in The Hoxton – we ate there one night and it was lush.

Where To Explore

I mean it would be rude to go to Chicago and not see the bean, right? It’s official name is ‘Cloud Gate’ and it’s handily located right by the Art Institute of Chicago which another absolute must-see. The bean gets busy during the day so if you want to snap ‘the pic‘ of it looking empty then early morning is your best bet. The museum though was bloody brilliant and has been voted the BEST MUSEUM IN THE WORLD for like five years now. Woah. Have a look to see if any exhibitions are on during your visit as we got to pop into the Andy Warhol one and it was fab. The other must-do is Skydeck Chicago which features a little ledge that you can step out 1,353 feet above ground level on. Erm, no thank you. Heights make my knees knock together, but I’m happy to report that you can take in the views from the middle of the room without your palms sweating. Another must-do is a visit to Second City; a sketch-comedy and improv theatre which some of my favourite comedians started off at. We saw ‘Deck The Hallmark’ and I chortled the whole way through.

Once you’ve seen the sights in the city centre why not take a little drive out to one of the neighbourhoods to have a nose around? We visited Lincoln Square, home to Bavarian-style bakeries and shops. If you head here then you have to pop your head into the Savoury Spice Shop, Gene’s Sausage Shop & Delicatessen, The Book Cellar and Merz Apothecary which was my beauty heaven – I could have spent hours in there. From there Andersonville is a short drive away, which combines it’s Swedish roots with small-town charm and a tonne of independent shops, bars and restaurants. If you want to do some vintage shopping then this is the place (Liv has some great recommendations up her puff sleeve), but I’d recommend stopping for a pastry or two at Lost Larson, before hopping over the road and emptying your wallet at Matha Mae’s on ALL THE STATIONERY. It’s worth only half-packing your suitcase for…


Photos by me, taken on a Olympus Mju II*

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