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Chicago City Guide

Author: Alice Chorley

I’ve always been in awe of America. As a child growing up in the Cotswolds, America seemed so far away. The glamour of LA, the craziness of New York, the cowboy-cool of the deep South. Fast forward a decade or two, and I’m now lucky enough to have been to America a few times chiefly because my husband’s best friend lives in New York. When he got married in St Louis a few months ago, we decided we would make a holiday of it – including a stopover on the way home.

Our research boiled down to a choice between Philadelphia or Chicago. Having spoken to a few people, we decided that Chicago sounded perfect. And it was.

So here are my tips, I can’t really do anything by halves so strap in for a long read…

Chicago: Where I Stayed

Now, I only stayed for a couple of nights so I really only have one specific recommendation but let me tell you, it was pretty amazing. We found The Robey on booking.com and managed to get a really reasonable deal. It was clean, comfortable and had oodles of style – quite handsome with dark green panelling, industrial metal touches – and the staff were also lovely and friendly. The hotel is in Wicker Park, which a particularly stylish friend had recommended, and I would totally double down on that recommendation as it’s a vibrant, fully caffeinated and unashamedly boozey up-and-coming neighbourhood that was still close enough to the main city to do all the touristy stuff.

Chicago: Things I Did

Architectural Boat Tour

I’m not exaggerating when I say that everyone, literally everyone, mentioned the architectural boat tour when we said we were going to Chicago and they were definitely right to do so. We were so lucky with the weather so the sun was shining and we sat on the roof deck (there is actually zero shade so do bear this in mind if it’s boiling) sipping an ice cold beer whilst listening to stories of the history of Chicago, as a cast of beautiful shiny buildings sailed by on either side.
The river weaves it’s way through the city and it seems the city has been defined, or even grown out of it.

The Riverwalk

If you’re more of a walking tourist then a sitting-on-your-bum tourist, the riverwalk is perfect. Part of the condition for developers creating new buildings along the river in Chicago is that the architects allow space for people to continue to walk along the river beneath it, making for an ever expanding river walk right through the city. The evolution of the city really has been defined by this thoughtful requirement so it’s a really interesting way of seeing how Chicago has been built up over time. I was blown away by how clean the city is so it is a really relaxing way to spend time walking along the river and stop by the various bars and cafes for food. It’s hard to imagine the river used to flow the opposite direction and was full of waste in previous years (as our architectural boat tour informed us!).

Lincoln Park

We headed to Lincoln Park quite quickly after landing and it was a great spot to stretch your legs. Lincoln Park sits on the edge of the city so is met by Lake Michigan and I loved walked through a leafy park to then see a busy but really clean beach. We didn’t go there but apparently the zoo, which is in the park, is worth visiting too.

The Chicago Bean

The Chicago Bean is actually called Cloud Gate and is a sculpture by Amish Kapoor, located in a pretty central area of Chicago. Again, everyone had mentioned it! You know that feeling when you say certain words so many times that they start to not mean anything? Yes, that. Chicago bean. The bean. Bean bean bean. OK we’ll go and take a look…
…I have to admit, it was impressive and good fun to view said bean. This giant statue is stainless steel but inspired by liquid mercury and the way it sits means that the city is constantly mirrored but contorted in its reflection. It was pretty special to see Mother Nature at it’s best – fluffy clouds, perfect blue sky – alongside the city skyline in a sort of warped perfection.
Incidentally, when I told my best friend (who I was in Chicago with) that I was writing this post he said that I had to call it ‘Chicago: Bean there, done that’. I’m not going to do that, but I’ve at least made that joke so we can move on…

Royal Palms Shuffleboard Club in Wicker Park

This is quite a specific suggestion but I loved it, so felt like it was worth mentioning. I have been obsessed with tabletop shuffleboard since playing it in New York a few years ago but this is the original floor version. Shuffleboard requires, to be honest, very limited sporting talent (hence why I like it) and is very similar to curling in that you attempt to knock your opponent’s disc (‘biscuit’) off a long, polished court.
The Royal Palms is something pretty special. Vintage-Florida inspired decor means that this place is not only super fun but is also made my dream of living in a Wes Anderson film come true. If the weather is nice, head upstairs to the festoon-lit rooftop and make sure you don’t miss a selfie with the flamingoes in the bathrooms. We chanced upon a local small brewery launch event on the roof, and having challenged the brewers to a game, we came away with free T shirts (sad to report they were commiseration prizes after they beat us by quite a long way).

Other things to do that were recommended to us but we missed out on…
Zanie’s – A well-known standup comedy joint where many of the comedians from SNL started out.
Art Institute of Chicago – An impressive institute housing some iconic artists including Monet, Andy Warhol and Edward Hopper.
Museum of Contemporary Art – Located near ‘The Magnificent Mile’ this museum features local and international artists supporting the diverse and interesting world of modern art.

Chicago: Where to Eat and Drink

Two rooftop bars to mention: “Cindy’s” and “The Up Room” at The Robey Hotel.
Despite living in London, visiting a rooftop bar still really excites me. I find it so romantic…the sprawling, chaotic city beneath you, the golden sun split between high rise buildings, a gentle warm breeze. Oh, be still my beating heart.
Luckily, there are lots of rooftop bars in Chicago, I would recommend Cindy’s (very close to the famous Bean so worth killing both birds with one bean) and also The Robey hotel has a gorgeous rooftop bar that was open to the public. One level even had an outdoor swimming pool (cue three awkward Brits getting very flustered after arriving and seemingly being thrown into what seemed to be a Miami Vice film… A few of them thought one of us was Prince Harry…) We took a dip in the pool just before checking out at 10am on a Monday, as such we had it to ourselves and it was magical.

Violet Hour

Signposted by just a single lightbulb hanging on a very unassuming street, this cocktail bar was one of the first speakeasies and set-up the framework for many others in the US to follow. We were totally blown away by the cocktails, which were really reasonably priced and very…punchy. Head here for a fancy pre-dinner cocktail before heading to…

Big Star

…for the best tacos and margaritas in town. Whilst the Violet Hour is beautiful and elegant, Big Star is it’s fun little sister. The atmosphere is really buzzy and the tacos were perfect for my hot-sauce-obsessed companions.

Deep Dish Pizza

You can’t talk about Chicago without mentioning the Deep Dish pizza. If you haven’t had it before, please, please try it. A proper deep dish is not like the frozen ones from the supermarket, it has a thick but somehow light crust with a cheese-webbed tomato-rich filling that almost makes it seem like a pie. Passing slices across the table results in a mozzarella cat’s cradle. It was so good it made me want to move my flight, just so I could fit in another dinner. Gino’s East is a staple for Chicago Deep Dish pizza and also has it’s own brewing company at the N LaSalle St. location.

After visiting Chicago, America is still an awe-inspiring place to me and if I haven’t made it obvious enough, I loved Chicago. To me it had the ‘good bits’ of my favourite cities – interesting food, great bars, amazing style but also a real identity…Chicago is cool, like really cool, but it doesn’t feel the need to show off about it too much. Where New York throws brunch at your face whilst honking its horn and running you over*, Chicago cradles you in its meandering river, calmly offering you another drink and asking how your day’s bean. BEEN, I mean been.

So – go. And eat a slice of pizza for me.

*Rough as that sounds, I do also love New York…

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15 thoughts on “Chicago City Guide

  1. I love Chicago! Has very special memories as this is where we got my engagement ring from an incredible antique jewellery shop – https://beverleyr.com – would highly recommend a visit to admire their lovely pieces!

    We also visited several of the Frank Lloyd Wright houses which were amazing.

    1. Oh that’s so special, Liz! What a lovely memory.
      I have to admit, I don’t know much about Frank Lloyd Wright, but having just read up on him, I wish we’d visited those houses too! x

  2. So glad you mentioned the deep dish pizza! Amazing! I’ve only been once, aged 11 as part of a month long trip in America with my parents and four siblings! Would love to get back at some point! A trip to Wrigley Field to see the Chicago Cubs play worth a mention too! “Bud light, Bud Light” – So American!

    1. I’m genuinely still thinking about that pizza.
      So jealous that you had a big US trip so young, I bet it was a lot of fun! Where else did you visit? x

      1. I’m Irish so we have a lot of American cousins and my Dad has been amazing at keeping up the link. The reason we were able to go was because we mostly stayed with family. We spent a week in Chicago, also visiting Wisconsin, then took an overnight train from Chicago to San Fran, which took three nights. My Dad had made the same journey aged 18 by bus and was keen to recreate. We saw amazing sights from the train. We visited San Fran, Sonoma, Yosemite, Lake Tahoe, Los Angelas, Santa Monica. Very lucky indeed

        1. Oh wow I am SO jealous! Amazing to have such a great link to somewhere. San Fran and LA are on my list. Hope you get to continue the trips!

  3. I love Chicago – I went there earlier this year for work – so limited sight-seeing BUT the one thing that everyone said i had to do was the architectural boat tour – and yes it was the perfect thing to do the day i landed – i wasn’t so blessed with the weather – but it was an incredible experience. I finished that trip totally blown away by Chicago which had never been close to the short list before – and i would love to go back and explore properly!!

  4. It sounds like you had a fab time. I love visiting the US and how different each place is – I’ve been to New York, Washington, Seattle and San Francisco (including Yosemite) – and love it when you find a laid back area. I think I may have to add Chicago to my wish list.

    I’d love to hear about St Louis too.

    1. Ooh would love to go to San Fran, Claire. How was it?
      St Louis was really interesting. Since we were there for a wedding, we didn’t get to fit in a huge amount of sightseeing but the people were incredibly friendly and welcoming, that was the main thing that stood out for me. They LOVE Brits! Also, the BBQ…Oh the BBQ! Food is definitely a running theme in my travel…

      1. San Fran was fun! We only had a few days there on the way to Canada, but it was enough to get a feel. We found some quiet areas to stroll around as well as taking in the shopping 😊 and having amazing Mexican food and margaritas – wish I could remember the restaurant name. I highly recommend taking the tram – it was almost like being on a rollercoaster at times. Exploring the piers and eating clam chowder while pelicans flew past felt quite surreal. Loved Alcatraz. The day trip to Yosemite was breathtaking – we wish we had stayed there overnight. It was a four hour drive through California with some amazing sights and an excellent guide.

  5. Another Chicago lover here! Having been once as a couple then again with a 10 month old (we were attending a wedding not too far away – in US terms at least!!) I would say there’s plenty to do both with and without kids. If you do go with kids I highly recommend staying around Lincoln park as it has a friendly feel to it and lots of nice cafes, shops and green places to stroll around (and close to the zoo as noted!) but not too far from the action of the city. Great recommendations!x

    1. Ooh nice to have some family friendly recommendations, thank you Amanda! My plans do generally focus around food and drink 🙂 x

  6. Totally unrelated but I’m really missing the daily posts and find I’m checking in less and less with you guys where as before it was one of the first things I used to do when I woke up. I remember a post about some changes for the summer but just wondering when things will be back to normal!

    1. Hi Bec, sorry to hear you’re missing the more frequent posts. We would love to produce daily content however it’s just not feasible as we’re such a small team. When someone goes off on maternity leave or for other reasons we don’t have the capacity for someone else to just step in to cover. Hope this explains things.

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