A Mini City Guide To Chicago

Our trip to Chicago was booked on a bit of a whim. I knew I wanted some sort of trip to mark my 30th birthday but couldn’t decide between a few dreamy baby-free days away to just lie horizontal without the background chorus of ‘MAMA! MAMA! MAMA!’ or whether I wanted to embark on some kind of #blessed #livingthedream #makingmemories family adventure that would likely involve a long-haul flight, a road trip, and lots of WHAT THE ACTUAL FUCK ARE WE DOING moments to equally match the Instagram bliss moments.

And then The Hoxton announced their cut-price rooms to celebrate the launch of their new Chicago hotel (I think we paid about £300 for four nights) and well, that was set. No toddler! No nappies! No constant chants for me to draw buses on scraps of paper!

So here’s my first impressions and mini city guide to Chicago.


WHEN TO GO – We went in September which was perfect as it was still warm but not suffocatingly hot, and there was plenty of pumpkin flavoured goods to perve on in WholeFoods. Chicago has freezing winters and pretty blazing summers, so spring and autumn are your best bets.


GETTING THERE – Flights take between nine and seven hours from the UK (it’s quicker coming back) and there’s a few different airlines available, including Norwegian Air and Virgin Atlantic. We flew with British Airways and paid around £375 for a return ticket per person, flying from London Heathrow.


WHERE TO STAY – I’ve stayed at The Hoxton Shoreditch before and loved it, so had high hopes for the Chicago branch. It has two restaurants, one downstairs bar, a fitness centre with daily yoga classes, a rooftop pool (which was empty on the days we used it and a great way to break up all the exploring), and is in a really great location in the Fulton Market District which is were all the cool food and drink places are popping up. I would highly, highly recommend. There’s also the Ace Hotel (another cool chain) or the Chicago Athletic Hotel Association which has Shake Shack located in the same building. Dreams really do come true.


AIRPORT TRANSFER – When we landed, my Google Maps kindly told me there was no way to get from the airport to our hotel using public transport, so we joined the taxi rank queue and paid around £40 for a 45-minute journey into the city. We did the same on the return journey, however – the blue line on the train system will take you from the city centre to the airport in 45 minutes for less than $5 per person.


GETTING AROUND – Aside from New York, Chicago is the most pedestrian friendly American city I’ve ever been to – it’s pretty easy to just explore on foot the way you would in London or Paris etc. We invested in three-day travel cards so we could use the train system which was fairly easy to navigate owing to the fact a) most of it is actually above ground and b) the lines are all named by colours: ‘ blue line’, ‘red line’ and so on. It was $25 for unlimited travel for 72 hours ($5 of that is refundable if you remember to give your card back – the equivalent of an Oyster, but we obvs didn’t).


CASH – I had about $80 in cash on me and only dipped into it once when the train ticket machine wouldn’t accept my card, the rest of the time I used my Revolut card as I would any other trip abroad.


PLACES TO VISIT – There’s lots of nice places to wander on foot – Millennium Park, Skyline Walk (down by the Planetarium) and the various mini beaches that lap Lake Michigan. There’s also a zoo, and a few museums (Art Institue Of Chicago, Museum Of Science and Industry and Museum Of Contemporary Art amongst others). It’s also well worth doing a boat tour, the most recommended being the Architecture Foundation River Cruise (which just FYI, serves alcohol).


INSTAGRAM HOTSPOTS – Chicago is actually a haven for bright coloured walls and murals, but you have to hunt them out as they’re not right in the city centre. I was recommended this Instagram account for a map of all the best walls. There’s also plenty of super sexy doughnuts in Chicago which make cute shots, and the skyline (as seen from either a boat on the river tour or from Skyline Walk) is also something special.


DOUGHNUTS – These are done crazy good in Chicago, so pack plenty of elasticated waistbands. The ones to check out are Firecakes, Stan’s Doughnuts and Do-Rite Donuts.


BRUNCH – The best brunch I had the entire trip (and probably my entire life) was from Little Goat Diner. You’d think Kung Pao Chicken on savoury pancakes for breakfast would be wrong, but oh lordy, so right. Other good spots included Beatrix and Cabra (which is in The Hoxton). The Fulton Market District was a hub for glorious brunches, it’s worth just going for a stroll!


LUNCH/DINNER – For quick and cheap lunches and dinners, our faves were Shake Shack, Lou Malnati’s pizza (who deliver, just FYI, and do the most infamous deep dish pizza in Chicago), and the food hall at Politan Row (which is seriously swank for a food hall, has pink bathrooms and does delicious bao buns). For a pricier dinner we loved Bad Hunter for excellent veggie options – the burrata was 27 kinds of incredible – and a super cool vibe.


IF WE WERE TO GO AGAIN – I wouldn’t actually do any of our stay differently, I adored it. I would have maybe done three nights in Chicago and then ventured on somewhere else, I would have loved to have hired a car for a few days and just explored  but I’d have had no idea in which direction to go!


BEST PART – Honestly, the hotel, its location and its rooftop pool really made out trip what it was. The food – especially the doughnuts, the pizza and that brunch – deserve special mentions.


WORST PART – I didn’t actually enjoy the city centre as much as I’d hoped, but adored the Fulton Market District. I guess you could compare it to not loving Oxford Circus and Leicester Square but loving Shoreditch.


OTHER CITY GUIDES – There’s this one from Liv Purvis and this one from Wish Wish Wish.



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