North America Travel · November 7, 2018

Chicago City Guide

Now, I knew this guide would take me a little while to put together. Although we were only in Chicago for about four whole days, it felt like we covered significant ground across the city and really got to experience the city from a local, and tourist point of view. It’s safe to say I absolutely fell in love with the city from the word go, and although we only dabbled in a handful of the cities colourful neighbourhoods- I know I’ll be coming back again- and not just for more deep-dish pizza! I’ve tried to include as much as possible for a really in depth insight to the city- but a huge thank you goes out to Choose Chicago for helping put an itinerary together and truly show us the best of what the city has to offer.


Chicago Athletic Association:

Of all the hotels I’ve had the luxury of staying in, Chicago Athletic Association has to be one of the most beautiful, homely and cool places I’ve ever set foot in. Housed in what used to be an exclusive sportsmen’s club, the hotel is absolutely drenched in history, from the original swimming pool tiles, motifs around the building and memorabilia lining the walls. It’s a property that has totally leaned into its history without feeling dated- and given it a new life with a contemporary edge (you can tell it’s designers were also behind the beautiful Ace Hotel in New York). Situated on Michegan Avenue, it’s in the heart of the city, boasts incredible views with it’s rooftop bar and restaurant, Cindy’s (which also comes highly recommended), it’s incredible Cherry Circle Room (which is out of this world) and also has the coolest Shake Shack (yes, really) I’ve ever seen that does in-room delivery. A total dream spot to rest your head (and even catch glimpses of The Bean too)!



The first bit of proper sightseeing we did was experience the city from the 103rd floor of the Willis Tower, at the SkyDeck- not bad for a first glimpse at the city. Boasting 360 views and giving you the option to literally stand over the city- it was a surreal and incredible way to start the morning- and a beautiful way of seeing the city from a true birds eye view.

Exploring the Neighbourhoods:

Although you’re pretty spoilt for choice with an incredible 77 neighbourhoods in the city, on our second day in Chicago we headed to the lower west side, and beautiful Pilsen. Starting at the National Museum of Mexican art, exploring here was one of my favourite things on this trip, and seeing the incredible street art and school mosaics really painted a picture (no pun intended) about what life in Chicago’s city suburbs are really about. On top of that, I also loved the Chicago Greeter initiative; ‘a free service provided by the Chicago Office of Tourism that matches visitors with enthusiastic, city-knowledgeable residents’- how brill is that?! Never feel lost in the city again, and get a tour from a local expert too, for free!

Shoreline Architecture Tour:

Although I’m not normally one for tours, this came recommended from locals and friends alike (honestly, so many residents said they’d done this themselves) and seeing the city from the three-branches of the Chicago River was a refreshing way of experiencing a new city. Learning about landmarks, hidden architectural treats and getting in some general knowledge was so rewarding, and although it’s pretty chilly on the river in winter- was worth it for the pub quiz points alone.

Buddy Guy’s Legends :

If you fancy a truly authentic evening experience in the city, may I point you in the direction of Buddy Guy’s Legends; the worlds premiere blues club and a fantastic place to grab a drink and catch some live music when the sun goes down.

P.S Also check out Thalia Hall and see if they’re hosting any gigs or events when you visit! It’s worth it for the open mic piano nights and cocktails alone!



Naturally the first thing Carrie and I did when we hopped off the plane was start thinking about where we were going to eat next. Although we were tired and slightly jet lagged, the calling of deep-dish pizza had us dressed and ready and before we knew it we had a table for two in iconic Giordano’s, and a pizza for two comin’ right up. Despite having no idea what to expect, we are officially both deep-dish converts, and I could certainly get used to a whole ball of mozzarella in an individual slice of pizza. Just make sure you don’t have any meals lined up for a while afterwards!

Doughnut Vault:

One place we’d had recommended time and time again was Doughnut Vault. Never one to say no to a holed good (give me cheerios and bagels any time of day), I was v. excited to try these iconic Chicago doughnuts. Picking the Buttermilk old fashioned, we were blown away by these delicious treats- but be sure to get there early- once they’re gone they’re gone, or alternatively…

C.C Ferns Coffee:

…head to C.C. Ferns coffee across town! Not only do they stock Doughnut Vault (great if you’re not one for queues) but it’s by far one of the coolest coffee spots I’ve come across. Packed with squidgy sofas and vintage furniture (more here), it’s the perfect place for some R&R.


I’ll be honest; Portillo’s had me at hot dogs. Something, although available in the U.K, we just don’t do as well as pretty much anywhere else in the world. Although typically a traditional fast food joint, these hotdogs are pretty damn special and it’s the kind of speedy lunch I can definitely get behind.

Big Star:

Gah! Can you believe before this trip I’d never properly tried tacos?! I know! All the ‘after this we’re getting tacos!’ merch that has been wasted on me for years! But, I admit I was missing out- and although I was convinced I’d never truly like them Big Star have a bloody good offering (their guac is deeelicious) and I highly recommend swinging by for tacos, nachos and beer (if you’re that way inclined)!

Summer House Santa Monica:

Although we only briefly stopped by here for a cookie break (and naturally to admire the interiors), I had this place down as a popular brunch spot, and judging by the number of empty tables (none) it’s pretty popular around here- I can also attest to their salted chocolate chip cookies, which I’m still dreaming about now.

Chicago Food Planet Tour:

From signature city dishes, West Loop favourites and must-eats whilst in the city- we took on the Chicago Food Planet Tour of Chinatown, and indulged in everything from dim sum to Szechuan- with everything from the best chicken I’ve arguably had to bubble tea (and everything in-between).

and if you’ve got room, head to…

Bombo Bar for exceptional gelato and hole-less Italian doughnuts with all the fillings, Dove’s Luncheonette (and not just for interiors, promise), BLVD for a very fancy decadent American style meal- ooer! S.K.Y for an exciting global inspired menu and finally Fulton Market for dinner drinks and art- swanky!


Knee Deep Vintage:

One thing that impressed me endlessly about Chicago was it’s incredible selection of vintage shopping. I feel like the U.S just has the most exceptionally diverse selection, and Knee Deep was one of my favourite shops we came across. With rows of carefully selected, well cared for pieces- it took a lot to not have a total field day in here and leave with more flammable blouses than sense- but I couldn’t resist a couple of finds!

Also to note: Una Mae’s for incredible designer vintage, shoes and homewares


One our third day in Chicago we did a shopping tour with the wonderful ChiTown Fashionista– a lady who certainly knows a thing or two about the cities hidden gems! Our first stop was P.45 in Wicker Park, a gorgeous womenswear boutique with every brand from Rachel Comey to Ganni in store- with some gorgeous pieces I’d never even seen before too…

Reckless Records:

Another shop I got very excited to check out was Reckless Records in Wicker Park. With rows of collector’s records (and new in artists too)- there’s something I always love about hitting up a record store in a new city (despite how pretentious that might sound) and this place is well worth a visit.

Moon Voyage:

One of the most gorgeous little shops in Wicker Park, Moon Voyage is a dreamy boutique stocking everything from independent jewellery designers, clothing and gifts- all with the most magical interiors.

Penelope’s & Gemini:

I absolutely loved coming across Penelope’s on our little explore around Division Street, and spotting it’s new sister branch next door (called Gemini) really made for a perfect pair. With Gemini stocking more contemporary brands including Paloma Wool and some gorgeous picks from A.P.C, Penelope’s boasts everything from childrenswear, menswear and stationery- making for a real retail power duo.


Could I really do a city guide without including a brilliant stationery shop? Could I? Really? Greer was probably one of my favourite little shops in Chicago, and although small- it packed a mighty punch. With rows of cards, paper, pens and notebooks- I discovered a handful of gorgeous brands hidden amongst these shelves, and even if you’re coming for a little desk inspiration you’ll definitely find it here.

Space 519:

Oh my god this place! Space 519 is in fact heaven on earth. All I knew before visiting was that it was ‘probably a cute concept store of sorts’- but really, without sounding cheesy- it’s so much more. With their gorgeous restaurant, Lunchroom (the interiors alone are worth a stop by)- a stationery and gifts section as well as beauty and womenswear- it’s a little pocket of heaven in a busy city, and certainly somewhere for a real treat yo’self moment.



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