Things to do in Chicago

I had heard Chicago was a city for foodies and art lovers, but I did not expect to also find amazing architecture, charming neighbourhoods and interesting history here. It was brilliant spending four days in the ‘Windy City’ last week, exploring with the Choose Chicago tourist board and discovering the diverse and varied range of activities on offer. Wrapped up warm we ventured out on a river boat tour, ate our way round Chinatown and visited a classic blues bar for legendary late night music. Here are a few of my must-do favourites from the trip… though there is plenty more I’d like to go back for!


To Stay

Chicago Athletic Association – This centrally located, historic hotel had years of restoration before its reopening in 2015. There are 241 luxury bedrooms along with a host of great facilities. Don’t miss Milk Room, a hidden eight-seat microbar with a carefully crafted cocktail menu made with only the rarest vintage spirits.


To Eat

Lost Larson – Andersonville, a neighbourhood on Chicago’s north side, is known for its Swedish roots. Lost Larson draws on this heritage, a charming Swedish bakery and cafe with the best Cardamon buns in town.

Big Star – This lively Wicker Park hangout is the place to go in Chicago if you have a Mexican food craving. With tasty tacos and great margaritas, you will never fail to have a good time at Big Star.

Little Goat Diner – The ‘Goat’ eateries are top of every foodies ‘to try’ list. There are three venues to choose from, all in the Fulton Market district. Each has a slightly different menu but all have the same mission; to present bold vibrant flavours. I tried Little Goat Diner, a favourite for brunch and loved the quirky dish ‘Little Piggy went to China’ (sesame cheddar biscuit with sunny side eggs, sichuan pork sausage and chilli garlic chive sauce).

Doughnut Vault – If the quaint exterior doesn’t convince you in to Doughnut Vault the scent of sugary goodness will. The tiny bakery has limited stock of their freshly made donuts each day, and they close up when they’ve all sold out. Try the Buttermilk Old Fashioned.

Lao Sze Chuan – This beloved Chinese restaurant serves up irresistible Szechuan cuisine. Found in the centre of new Chinatown, the service is attentive and the prices reasonable. Order the Dry Chilli Chicken and the Garlic Eggplant.

Longman and Eagle – A brunch institution, Longman and Eagle is a hipster spot in Logan Square. The kitchen is known for its farm to table fare… opt for the waffles and fried chicken.

Stan’s Donuts – Stan’s Donuts has long been a favourite for donuts in its LA and California branches. The 50 year old donut company now have several branches in Chicago offering an endless range of donuts, in every flavour imaginable. There are vegan and gluten-free options too.

Dove’s Luncheonette – This easy-going Wicker Park diner is a great weekend brunch option. The interiors are classic and nostalgic and the menu is filled with American comfort food. Sit at the bar and soak up the atmosphere.

Lou Malnati’s – Chicago is known for its Deep Dish Pizza. There is lively debate about the ‘best’ establishment, but Lou Malnati’s features on every must try list. The high-edged pastry leaves plenty of space for layers of cheese, tomato sauce and toppings of choice. Filling, gooey and dangerously delicious.

Bang Bang Pie – For the ultimate afternoon treat head to Bang Bang Pie, where the wholesome pies and savoury dishes satisfy every appetite. The interiors are rustic chic and the service is among the friendliest in Chicago. Try a slice of the Key-Lime Pie or the Autumnal pumpkin pie.


To Drink

Sawada – This is the first U.S. coffee shop from world renowned barista and latte art expert Hiroshi Sawada. The coffee is delicious and poured to perfection. Stop by the Fulton Market cafe for a donut and drink… Sawada are known for their matcha drinks, mixed with chocolate and coffee.

CC Ferns – A quaint coffee house in Humboldt Park. The vintage interiors make CC Ferns perfect for a cosy afternoon drink, and the venue is always filled with hipster locals. The cafe offers Doughnut Vault donuts and housemade croissants to accompany your coffee.

Intelligentsia Coffee – There are lots of branches of this failsafe speciality coffee brand in Chicago. The coffee is smooth and delicious, and it’s one of the only independent cafe options in Downtown Chicago… the perfect caffeine-kick to go while you go sightseeing.

Cindy’s Rooftop – The rooftop bar at the top of the Chicago Athletic Association, Cindy’s has a menu of great cocktails and the best panoramic views.

Four Letter Word – Heisner, Ria Neri, and Eylem Ozkaya opened their first coffee shop & roastery in Istanbul serving Turkish-style coffee and single-origin coffees from Central & South America. They have recently opened a second cafe in Logan Square in Chicago and serve some of the best coffee in town. (Opposite the brilliant neighbourhood restaurant, Cellar Door Provisions).

Lost Lake – A tropical tiki bar in Logan Square, Lost Lake is recognised as one of the best cocktail bars in Chicago. The menu pays homage to 80 years of exotic cocktail history, order a bourbon based ‘Hazy Lazy, Like, Kinda Crazy’.


To Do

The Art Institute of Chicago – The Art Institute of Chicago, located in Grant Park, was founded in 1879 and is regarded as one of the finest art collections in the world. Wander round the many galleries exhibiting old masters and modern works while looking out for paintings by important artists such as Georges Seurat, Edward Hopper and Grant Wood.

Shoreline Sightseeing Architecture River Tour – Chicago is known for its architecture around the world. This 75-minute boat tour is a great way to see 40 city landmarks, while listening to the expert guide explain the engineering and history behind some of the most prominent skyscrapers.

Buddy Guy’s Legends – This classic blues bar is famous in Chicago for its brilliant band line-up. Head to Buddy’s for the best blues music in town and New Orleans inspired grub.

Skydeck – Head up to the 103rd floor of the Skydeck to see incredible views of the whole city, 1,353 feet below. The building is the highest in the Western Hemisphere, if you are brave enough stand in the overhanging glass boxes for an even more immersive experience.

Chinatown tour – The Chicago Food Planet tours are fun and informative. We enjoyed a 3-hour tour of old and new Chinatown, with 5 tasting stops while also learning about the history of the area. For a more general neighbourhood tour I highly recommend ‘Chicago Greeter’, free tours run by enthusiastic volunteers.


To Shop

Martha May Art Supplies & Beautiful Things – This little pink shop is found in the charming neighbourhood of Andersonville in the north of the Chicago. Named after owner Jean Cate’s pet dog Martha, this shop is carefully curated with lovely stationery, specialist art supplies and beautiful objects.

Bari Zaki – Bari Zaki is a wondrous emporium of wonderful stationery and creatively bound books. The shop also hosts bookbinding workshops for those keen to learn the skill.

Norcross & Scott – This lovely furniture and design store is found in Andersonville. The selective collection includes accessories from Tom Dixon, Bend Goods and Norcross & Scott’s own range.

Koval – Established in 2008, Koval is Chicago’s first distillery since the mid-1800s. All the Koval organic craft spirits are made from scratch, and the company is particularly well known for their whiskeys, though they also make vodka, gin and liqueurs. The simple packaging is very stylish, making a bottle of Koval a great gift to take home.

I visited Chicago as a guest of Choose Chicago, more information on the destination here.

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