CHICAGO; A CITY GUIDE.
Chicago is somewhere I’ve been wanting to visit for a really long time– you know that I love exploring a new city and after having seen to New York and San Francisco, Chicago was next on my list. So when I was very kindly invited by Choose Chicago to spend five days in the city, I jumped at the chance to finally see some iconic Chicago favourites and to explore some less well known neighbourhoods too! I had the best time and I’m really looking forward to sharing this city guide with you– there’s a mixture of things to do, places to eat and drink and one really beautiful place to stay & I hope that whether you’re planning on visiting Chicago soon or not, that you enjoy this look into how I spent a few days in the city.
Things To Do
The Art Institute of Chicago
A must when you’re in Chicago– The Art Institute of Chicago– is one of the oldest and largest art museums in the US. It has a permanent collection of nearly 300,000 works of art and lots of yearly special exhibitions– we had a chance to see the Andy Warhol exhibition while we were there which was really interesting. The museum itself is beautiful and on it’s own is worth a visit, you can definitely see why it’s called a Chicago landmark.
The Art Institute of Chicago.
Skydeck
One of Chicago’s most popular tourist attractions and for good reason, the Skydeck at Willis Tower is the best way to get the view of the city & if being at 1,353 feet wasn’t enough you can head out on The Ledge where you get a clear view straight down to ground level. One of my favourites things when visiting a city is to see the views from above so this was top of my Chicago must see list and it definitely didn’t disappoint!
Skydeck.
Lincoln Square Neighbourhood Tour
Chicago has so many diverse and individual neighbourhoods to explore (there’s said to be anywhere between seventy seven and two hundred) so if it’s your first time in the city I highly recommend exploring a different area of the city with a Chicago Greeter. It’s such a unique and one off experience– getting a free tour from a Chicago local who all volunteer to be a part of the program– you get a chance to see things you might never find in a guidebook. We took a tour around Lincoln Square, a German American neighbourhood with some lovely independent shops and a lot of history.
The Second City
Another Chicago icon– The Second City– is the place to visit to catch a live comedy show. If you haven’t heard of the improv & sketch comedy theatre then I’m sure you will have heard of some of the alumni, it’s where people like Steve Carell & Tina Fey started their comedy careers. They do a show every night of the week so plenty of opportunity to see some comedy. Usually comedy can be a bit hit or miss for me but the show we had the chance to see– Deck The Hallmark– was so much fun, I loved it!
The Second City.
Shop
Open Books
I wanted to add at least a couple of shopping recommendations in this guide and of course I had to include a bookshop. Open Books is a community, non profit bookshop stocking thousands of donated used books and they have a couple of stores in the city, in West Loop and Pilsen. I visited the one in West Loop as it was just a few minutes away from The Hoxton and I meant to just have a quick browse but ended up staying for an hour, it’s just one of those places you could stay all day, with a shelves and shelves of books, comfy chairs & reading nooks.
Open Books.
Martha Mae
I heard so many good things about Martha Mae in Andersonville and seen the shop described as a work of art and that’s exactly what it is– a stationary lovers dream full of beautifully laid out art supplies, notebooks, planners and things for the home too– I definitely regret not picking something up from here! Even though we didn’t spend long in Andersonville it was a great area full of independent shops so definitely a place to visit if you’re looking for a gem similar to Martha Mae.
Martha Mae.
Even though I didn’t have a whole lot of time for shopping here are a few other recommendations that I did get the chance to have a quick browse of–
For really good and affordable vintage try Knee Deep in the Pilsen neighbourhood.
In the previously mentioned Lincoln Square neighbourhood– try independent Merz Apothecary for part old fashioned pharmacy, part well stocked beauty store & independent bookstore Book Cellar for the newest releases and a cosy cafe serving wine by the glass.
Eat & Drink
Doughnut Vault
We visited Doughnut Vault first thing on the first morning we were in the city– we’d heard it sells out quick so made it a priority! I went for a coffee & a classic buttermilk and it was for sure the best doughnut I’ve ever eaten, it’s obvious why this place is so popular. The tiny shop on Franklin St is very pretty, too small to sit in but it’s the perfect place to grab your doughnut to go and start your day of exploring!
Doughnut Vault.
Summer House
The perfect spot for some laid back Californian vibes in the Lincoln Park neighbourhood of Chicago– Summer House Santa Monica is inspired by the west coast– think light and bright, beach house decor and Californian inspired menus but still with a little hint of Chicago. We visited for lunch and the decor is truly dreamy and took me straight back to being in Santa Monica. Food wise I can highly recommend the Brussel Sprouts Salad and the Grilled Cheese if you’re looking for a great mixture of a California and a Chicago style lunch!
Summer House.
Bang Bang Pie
It just made sense for us to make time for some pumpkin pie, especially on the day before Thanksgiving so we headed to Bang Bang Pie– a very popular spot in Chicago. They serve custom roasted coffee, sell pies whole or by the slice and if that isn’t classically American enough for you they also serve biscuits and grits. We got a few slices between us– the pumpkin, the apple and the chocolate pecan & although it feels wrong to pick a favourite I think I'd have to go with the apple!
Bang Bang Pie.
Lost Lake
If you’re happy to head out of Downtown for the evening then be sure to make your way to Logan Square– we started the evening with dinner at Longman and Eagle and then onto Lost Lake– a tiki cocktail bar with a touch of 1930’s Hollywood glamour. Not only do they have an amazing selection of tropical cocktails, including non alcoholic options, but the decor & the way they present the drinks really adds everything to the atmosphere! Fully deserving of the title of Time Out Chicago’s Bar of the Year (2018).
Lost Lake.
Dusek’s
A super cool and well renowned, Michelin starred restaurant in the popular Pilsen neighbourhood– Dusek’s is definitely one to add to your list if you’re planning to visit Chicago! It was one of my favourite places we visited– the mix of the more casual & cosy setting and the really good food made for the perfect lunch spot. They have brunch, lunch and dinner menus & are well known for serving a wide selection of beer and cocktails too.
Dusek’s.
Sawada Coffee
You know that I love a coffee shop and I have to say that Sawada Coffee is one of the coolest I’ve come across. Perfectly positioned in the Fulton Market District– the industrial vibes and a great coffee menu definitely make it worth visiting & as a bonus they stock a selection of Doughnut Vault doughnuts. It’s a popular spot so if you want to guarantee a seat (and a doughnut) make sure to visit earlier in the day!
Sawada Coffee.
Giordano’s
No trip to Chicago is complete without trying deep dish pizza– it’s probably the food most associated with the city and out of all of the eateries offering deep dish, one came particularly recommended– Giordano’s. When it comes to pizza I’ll usually order the thinest option on the menu and this kind of Chicago pizza is basically the opposite but after finally trying some, I can see why deep dish is such a classic. Giordano’s has been serving their stuffed pizza as well as salads, pastas and sandwiches since 1974 and they have plenty of restaurants all over the city so make sure to visit one while you’re in Chicago!
Giordano’s.
Just because I don’t think you can ever have enough Eat & Drink recommendations here are a few more–
For contemporary ‘inn style' dining with a focus on farm to table food try Logan Square neighbourhood favourite– Longman & Eagle.
For great coffee, beautiful interiors and quite possibly the best pastries you’ll eat in Chicago, make sure to visit Lost Larson in Andersonville. We tried a few of their fresh baked goods and everything was delicious but if I’m picking favourites mine was the Cinnamon Roll.
If your struggling to decide where to eat, try Time Out Market in the Fulton Market District for the best of the city, including some of Chicago’s best chefs and most popular restaurants all under one roof. My recommendations– Arroz de Grelhos from Abe Conlon, Devils Food from Sugar Cube & Rainbow Chip Fancy Pop from Pretty Cool.
Stay
The Hoxton
Since being introduced to The Hoxton brand a few months back, I’ve really fallen in love with everything they do and The Hoxton in Chicago is no exception. One of the newest hotels of the brand, it’s the perfect place to call home while you’re in the city. The location– the Fulton Market District– is a great spot for exploring more of the city, the restaurant offerings are headed up by Chicago’s finest & the interiors are a mid century dream. I recently shared more details and thoughts on The Hoxton, Chicago in a blog post which you can find here!
My trip to Chicago and my stay at The Hoxton were courtesy of Choose Chicago. As always all content & opinions are my own.