48 Hours

48 Hours In Chicago

April 1, 2020

I spent four days in Chicago for work, and despite feeling jet-lagged and zonked for a lot of it, I totally loved the city. On the surface, it’s a lot like a chilled-out New York, with the same Downtown glassy skyscrapers, impressive waterside skylines, buzzy energy, and hip neighbourhoods to hangout in. But when you dig a little deeper, you appreciate its uniqueness — from its world-class art scene, to its Obama ties, native deep dish pizza, and a rich music history, spanning jazz, blues and house. I stayed at The Hoxton (naturally) which serves as the perfect base for a few days exploring. Located in Fulton Market District — a recently developed neighbourhood that’s seen industrial buildings converted into hip eateries, craft breweries and slick hotels — the hotel puts you in easy access of everything, right where you want to be. Here’s how to do 48 hours in Chicago…

see + do

Cloud Gate

Ah! The shiny silver bean I’ve wanted to see for years and years. Anish Kapoor’s Cloud Gate totally lives up to the hype and is just as special IRL. Located Downtown, right near the water, it’s a popular spot so expect a crowd from morning ’til night. That said, make the most of your jet-lag and get up and out before breakfast, because if you’re there before 8am, you’ll get it pretty much to yourself. I ran there from The Hoxton a couple of mornings because I was stuck on London-time, plus wanted that shot.

The Art Institute of Chicago

I didn’t get chance to squeeze in a visit to THE ART INSTITUTE OF CHICAGO and I really bloody wish I did, especially as there was a Hokusai exhibition on at the time I’d have loved to have seen. Not only famous for that Ferris Bueller scene(!), it’s one of the oldest, largest  art galleries in the United States, hosting a world-class international collection. Fans of the more out-there, contemporary genres might want to pay MUSEUM OF CONTEMPORARY ART a visit too, not least of all for its great restaurant, Marisol.

The Green Mill Room

GREEN MILL is the ultimate place to end a night in Chicago. The Uptown jazz club was said to be Al Capone’s favourite hangout —so much so he had his own table that you can still sit at today, complete with a telephone for calling the ladies during the Prohibition era lock-ins. As soon as you’re inside, you’re transported back in time. Dimly lit and slightly mysterious, with a sophisticated informality, and warm, cosy atmosphere, it’s a totally unique and a must-do in Chicago. There’s a $15 cash cover charge, but I’d say its totally worth it for the experience. Order a night cap and settle into enjoy the music.

Kingston Mines

Somewhere between a dive bar and a gig venue, KINGSTON MINES is another iconic Chicago institution that’s been showing people a good time since 1968. Located in ‘Blues Alley’, here is a lot more lively than Green Mill Room, with no seats or cosy booths, but live music ‘til late. Grab a beer or something stiffer and enjoy a boogie Chicago style.

Lost Girl’s Vintage

The coolest vintage store in the city, LOST GIRLS is a must visit — and that’s coming from someone who doesn’t ever shop vintage. Instagram gold, it’s all hot pink inside with eclectic decor details and a great mural, so so tightly curated you’re guaranteed to only find good stuff. Prepare not to leave empty handed!

Second City

I wouldn’t say I’m a big fan of comedy usually, but I absolutely loved our night at SECOND CITY — an improv-based sketch comedy institution, which has live shows every night and is where the likes of Tina Fey and Steve Carell cut their teeth. I laughed out loud to the whole of She The People. Check online for tickets in advance, but I highly recommend it for something a little different to the norm.

Wander around Bucktown and Wicker Park

There’s loads going on in Downtown, but the coolest neighbourhoods to wander around are west of the centre, like Fulton Market District, Bucktown and Wicker Park. Here, you’re gonna find a slightly more chilled out pace, great bars and coffee shops, vintage stores and independent boutiques. Stop for coffee at LA COLOMBE in Wicker Park, or get tacos and margs at popular spot, BIG STAR.

eat + drink

Lou Malnati’s

No-one should leave Chicago without trying a deep-dish pizza. It’s a rule, regardless of how loyal you are to the thin, crispy sourdough types us Londoners are far more familiar with. Ask any local where to try the best deep dish in town and they’ll all say LOU MALNATI’S: a longstanding local chain which has a couple of locations, the best of which is said to be on N Wells St. Don’t go in a rush because pizzas take up to 45 minutes to cook, plus, you’ll probably have to wait for a table. I’m not convinced I’m fully sold on Chicago’s famous deep-dish variety, but it’s definitely worth trying.

Lost Lake

Slightly out of the way in the Logan Square neighbourhood but very much worth the pilgrimage, LOST LAKE tiki bar is the best spot for cocktails, not only for drinks themselves which are full of alcohol and flamboyantly served in quirky cups with umbrellas, colourful streamers, and even dolphins carved from banana skins, but for the vibes and eclectic decor too. Lampshades made from puffer-fish and bamboo furniture surely helped win the title of Time Out’s Best Chicago Bar in 2018.

Girl and the Goat

You can’t come to the States and not do a big, fat American brunch. GIRL AND THE GOAT is the place to get it…if you can get a table. The vast menu spans sweet and savoury, with everything from pancakes to French Toast, shrimp and grits,  lox bagels, and a plethora of sides to go with. Filter coffee is unlimited (and served in bucket-size mugs) and hard shakes are recommended. Nearby, DUCK DUCK GOAT and LITTLE GOAT DINER are just as good for more of the same (the Boka Restaurant Group have a real monopoly over Fulton Market District!)

Sawada Coffee

A damn cool, casual spot in Fulton Market District, SAWADA COFFEE is basically a coffee shop come co-working space, come fun bar and BBQ restaurant. I don’t really know what it is. All bench seats, festoon lighting, and rough-and-ready Hell’s Angels-esque decor, it’s a fun place to take five — the iced lattes are creamy, huge and delicious.


The ground-floor restaurant in The Hoxton hotel offers a welcomed change from huge, heavy American portions with its light and elegant Mediterranean small plates that are perfect for sharing round the table with a bottle of wine. Favourites were the deep fried olives (insane), beets with cucumber and buttermilk, and salt cod with harissa. Easily one of my favourite meals in Chicago.


If you’re a fan of Asian food (I always try to scope out the best wherever I am in the world), get to HAISOUS, a fantastic husband and wife-ran modern Vietnamese restaurant in the very cool Pilsen neighbourhood, to the southwest of the city. We went for a late brunch and ate so much amazing food — it makes a nice change to your usual American brunch options. The fried chicken wings are a must order, and the lotus stem salad is super fresh and tasty. Don’t miss their egg custard coffee. Sounds weird, tastes unbelievable!


If you weren’t sold on Lou Malnati’s, GIORDANO’S is said to the other best deep-dish pizza spot in town, with a more flavoursome tomato sauce and slightly different crust. I’ll let you decide…

Two Lights

A nice dinner option, TWO LIGHTS is an elegant, laid-back spot for seafood. Go wild for their menu of lobster rolls, juicy scallop rolls, oysters, dill fries, and more, all to be washed down with a couple of their signature cocktails. There’s also a great Mexican place next door which you should visit pre- or post- dinner for a great Margarita.

Al’s Beef

Another Chicago staple is (apparently) an Italian beef sandwich. AL’S BEEF if the place to get it, which has a handful of locations scattered across the city.


The Hoxton, Chicago

Biased, yes, but THE HOXTON, CHICAGO serves as an excellent base for a few days in Chicago. Rooms are spacious and über-comfy with cloud-like beds and luxurious walk-in showers. Big windows let in loads of natural light and offer great views of the neighbourhood, and mid-century fans are sure to go wild for the furniture. The large lobby buzzes day and night and is a great spot to kill an hour or two, nursing a coffee or a cocktail. To top it off, there’s a rooftop too, complete with killer views, a plunge pool, and a highly acclaimed Peruvian restaurant, CABRA, that’s headed up by one of Chicago’s top female chefs.

tips worth knowing before you go

Traffic from Chicago O’Hare airport is pretty dire, and you’ll end up spending a long time sitting still if you choose to take a cab. If you haven’t got heaps of luggage, I’d say take the train. It’s the easiest, cheapest option by far, just straight on the L train to the middle of town.

Don’t forget to sort your ESTA before landing in the US or else there’ll be hell to pay when you land — in fact, you’ll probably be sent home. US Customs are some of the strictest around and they aren’t usually up for a laugh. Apply online at least 72 hours before you depart to make for a stress-free trip.

Tipping culture in the States always gets me. Most places let you easily add tips on to bills via card, but it’s worth carrying cash too for tipping for drinks in bars and taxis.

Chicago is city that’s super easy to walk around, with most of the key ‘sights to see’ located in Downtown. To hit up some of the cooler neighbourhoods like Wicker Park and Bucktown, make use of the subway system. It’s cheap ($2.50/ ride or $10/ day) and easy enough to navigate.