10 favorite things to do / chicago

my friend mary kate has been everywhere. i met her on my london study abroad, she lived in florence and russia for a time, and has the coolest stories. she also did an internship in chicago- which is currently (especially after this post) on the top of my list of cities to visit. i can't believe i haven't been yet. check out her recommendations!


A few years ago I was lucky enough to find a job in Chicago with a VC firm.  I moved to the city into a tiny one room apartment with beautiful view.  Though I spent the majority of my time in the office, I took every spare second to enjoy/explore the city.  Here are the top 10 most interesting parts of the city:

1.     The Art Institute 

This museum is very nearly my favorite in the US.  The collections are incredible.  My favorite thing in the museum is a collection of tiny busts done by Honoré-Victorin Daumier.  There is nothing better than a snarky political Frenchman expressing himself through sculpture.  I couldn’t choose a favorite painting but I guarantee you will love them all! (I remember being able to get some sort of discount if you go late in the afternoon/evening but can’t see it on the website so maybe ask about it when you are there.  If that is not available admission is free Thursday from 5-8pm.) 

2. Take an architectural boat tour 

The architecture in Chicago is incredible.  It is rare to be able to sit on a boat and look at/ learn about some of the most fabulous architecture out there.  Chicago is unusual because it has a river running through the center of the city.  The rides are a fun way to get a feel for the city.

3. Bandera 

Chicago is a city for food.  The extreme temperatures are great at driving people into restaurants.   My favorite is called Banderas and is conveniently located right on Michigan Ave but is a bit tricky to find.  Look for a big sign on the second story above a Citibank, enter through the door to the left of the bank that is for a fur shop or something Russian like that, take the escalator up and it is on your left.  The food is to die for! You can’t go wrong ordering but I would make sure to order both desserts even if you are alone.  House-made Oreo Ice Cream Sandwiches and Banana Cream Pie with Carmel and Chocolate.  

4. Michigan Ave 

Michigan Ave is the main shopping street in Chicago it is nicknamed “The Magnificent Mile.” It is an easy street to stroll down while looking at blocks and blocks of shops.  My favorite places to drop in on include the appropriately punk British brand All-Saints, the America classic NIKE, and the random Fourth Presbyterian Church with an incredible courtyard tucked away between the hundreds of stores and towering buildings.


5. Rush Street

If you were looking for somewhere a little less crowded I would recommend Rush St.  Rush runs parallel to Michigan and in my opinion has better shopping; more little boutiques, the better major department stores/designers, and it is where many of the showrooms for my favorite sports cars reside.

6.The BEAN

The Bean is a must for anyone visiting Chi Town.  It is so odd/incredible you just can’t miss it.  It is located at the entrance to Millennial Park which is also pretty sweet.  If you look online beforehand, you can almost always find something free going on, a concert, an extreme yo-yoing competition, a yoga class, etc.  Awesome.

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7. Navy Pier

May be the most touristy thing to do in Chicago but it is also kind of fun.  There are rides, games, carnies and much more.  As an added bonus there is a firework show twice a week during the summer.  

8. Armatige Ave

The last of the shopping streets mentioned in this top 10 is Armatige Ave.  This street is a little more off the beaten path but is fun because it gives you a chance to see some of the charming Chicago neighborhoods.  Again this is a street where you will find more funky shops and delicious gelato. 

9. Willis Tower

Previously known as Sear Tower, was the tallest building in the world until 1973.  Now it is the 8th tallest.  I never actually went to the Tower, for whatever reason I wasn’t into it.  But, I did have many friends who were into it and they loved it.  Whether you choose Willis(Sears) or not you definitely need to find somewhere to get a view of the city from on high.  

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10. The Donut Vault

Of course we have to end with something sweet so I will tell you about the secret treat the locals die for…The Donut Vault.  It is basically this tiny closet of a bakery with a line that wraps around the block but boy are those donuts good.  If you get there around 8am you are usually good.   They open at 8:30 and stay open until they sell out which is fast.  Glazed Chestnut is my fave but since you are already there and awake you should probably get an assorted box just so you can try them all.  400 N Franklin St, Chicago 60654

That’s it for the top 10.  Here are two bonus stops that didn’t make the list because they can be a bit sketchy but if you are looking for more to do and are feeling brave, give them a go.  The old meatpacking neighborhood (where I used to office) is the up and coming hot spot in Chicago.  It has some awesome restaurants (Wishbone), and shops.  Greek town also has great food, but don’t forget yo mace!

Happy Travels!