Lake Shore DriveThis is a big stretch on the water, it will lead you from Adler Planetarium to Buckingham Fountain (a should see.. that’s where Lollapalooza always is, also most likely where the food festival will be going down when you’re in town).

John Hancock Center.  Have a drink in the Signature Room. I arrived at 11am and ordered a glass of prosecco because, well, why the hell not.

Art Institute of Chicago.  It’s free, and right down on Michigan Avenue, close to The Bean and Buckingham Fountain.  A couple of famous pieces of art you must see are, American Gothic – you may know it, it’s the one with the farming couple with the pitch fork – and A Sunday Afternoon on the Island of La Grande Jatte.

The Bean (also known as Cloud Gate), is the large metal thing that everyone takes a photo of their reflection in. Go on, do the same.

Willis Tower (a.k.a. Sears Tower).  There are two glass boxes called the Sky Deck, that jut out of the building that you can stop out onto and look all the way down. It’s terrifying but worth it.  that you stand on that jut out of the building, it is pretty insane. 

Millennium Mile or Magnificent Mile is where the shopping is.

If you have time, go see a Cubs game (or White Sox). 

Make sure you do the architecture river cruise.  It’s a beautiful way to see the city and learn some history, whilst also getting a chance to show off your Good Wife skills. 

Go to Wicker Park for great boutiques and delicious tacos and whiskey at Big Star.


The Publican, West Loop. Amazing oysters, BBQ pork and wine.

Little Goat, West loop – High end diner with an amazing mixed menu.

Girl & The Goat, West Loop. The hot spot with quirky menu.

BellyQ, West Loop. Killer Korean BBQ

Doughnut Vault, West Loop. Doughnuts from a caravan. What’s not to love.

Big Star, Wicker Park. Delicious tacos and whiskey.

Quaortino. Delicious Italian tapas.

Garret’s Popcorn. They have one of Magnificent Mile. Get the fix – it’s dangerously addictive.

Neither tried nor tested, but researched & recommended…

Green Street Smoked Meats, West Loop. Killer BBQ and smoked meats in an awesome outdoor setting.

Fig & Olive, Gold Coast. Seasonal menu with plenty of figs and olives.

Freds @ Barneys, Gold Coast. The roof at Barneys with great views.

Avec. Shared plates, minimalist setting and communal tables.

Gilt. Fancy bar and lounge with a mixed menu and killer cocktails.

RL – Ralph Lauren’s restaurant, if you like that kind of thing! 


Violet Hour. A secret bar opposite Big Star in Wicker Park. Cocktails ‘n’ stuff.

Maude’s, West Loop. Quirky and cool bar with good bar snacks.

Soho House, West Loop. More choice.

The Betty, West Loop. Nice bar and friendly staff.

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