Chicago’s Gold Coast: Fig & Olive and More Cupcakes


Chicago’s Gold Coast neighborhood is known for its historic houses around Astor Street, the legendary Pump Room in the Public Chicago hotel (formerly the Ambassador East) and designer shops on Oak Street.  Speaking of Oak Street, there is a swanky, new restaurant called Fig & Olive which is tucked away on the north side of the street, near Dolce & Gabbana and Christian Louboutin.  Earlier this week, I stopped in there for a lovely lunch.


Fig & Olive


Fig & Olive is located

3 blocks south and 4 blocks east of the Clark/Division ‘L’ stop, along the CTA Red Line.  The #3 King Drive bus which runs along Michigan Avenue/the Magnificent Mile also stops nearby.




After exiting the elevator at 104 E. Oak St., I stepped into the sleek, pretty space of Fig & Olive. There is a stunning bar with a tree growing in the center of it.  Very cool!  You can choose to sit and eat there or at one of the very comfy tables in the main space.  I chose the latter.


The bar at Fig & Olive in Chicago

Fig & Olive on Oak Street


Fig & Olive has a menu which is focused on Mediterranean fare with nods toward Italy, France and Spain.  All of the food is cooked or finished with various olive oils from those countries.  No butter is used in any of the dishes.  Olive oil has always played an important role in my life.  It keeps me healthy on the inside and glowing on the outside.  Seriously, I often use it on my skin rather than lotion 🙂  Anyone else?

For lunch, I began with this complimentary olive oil trio and rosemary olive oil fougasse bread.  The first oil was fruity, the second was herbaceous and the third (my least favorite) was a bit grassy. Needless to say, I consumed all of it.  Don’t judge.  It’s cold outside and I must take care of myself 😉


Olive oils at Fig & Olive

Complimentary olive oil trio with rosemary olive oil fougasse bread


Since I have not eaten pasta in a good while, I decided to order this wonderful penne sauteed with cremini and truffle mushrooms, scallions, Parmesan cheese and a generous amount of white truffle oil.  At first, I found the flavors quite nice, although not as bold as I had expected.  Then, I thought better to give this dish a good toss to more evenly distribute the abundant white truffle oil against the other ingredients and the steam from the pasta.  Perfetto!  I ate it all.  It was a very light dish considering the amount of penne.  If you are looking for a pasta that will not leave you feeling blown up, this is the dish for you!


Pasta at Fig & Olive

Penne with cremin and truffle mushrooms, scallions, Parmesan and white truffle oil


I washed it all down with a lovely glass of Spanish Cava.  After all, I was a lady who was lunching 😉


Cocktails at Fig & Olive

A glass of Cava to wash it all down


Fig & Olive is a great place to come with a few friends, so you can sample several of the flights from the crostini bar, some crudo and other shareable plates.  Even if you can’t afford to drop some cash in the shops along Oak Street, Fig & Olive is lovely splurge.

I want to give a shout out to my wonderful server, Joe.  He was super nice, attentive and very knowledgeable about the menu.  I will be back soon.

On my way home, I decided to stop in at another decadent spot, More Cupcakes, on the corner of State and Delaware Streets.  


More cupcakes in Chicago


Chicago has no shortage of yummy and interesting cupcakes shops but this one has the very best ingredients.  The cakes themselves are the lightest I have had to date.  It’s difficult to choose among the many flavor options.  However, I love all things lemon.  So, I had to have this beautiful lemon meringue cupcake.  



Sooo lemony!


The cake was filled with the most tart and lemony cream and it was topped with perfectly stiff and slightly crispy meringue peaks.  I should have ordered another one.  Regrets are a bitch!


Lemon meringue cupcake at More


I also tried this Grand Marnier cupcake.  Although the liquor flavor in this cupcake was much more subtle than the lemon in the lemon meringue cupcake, I was still really impressed with how light, moist and beautiful it was.  The thick frosting was really delicious.


Grand Marnier cupcake at More Cupcakes

Grand Marnier cupcake


Grand Marnier cupcake

Grand Marnier cupcake


The next time you are looking for some decadent spots in Chicago’s Gold Coast, check out Fig & Olive and More Cupcakes.

Fig & Olive is located at 104 E. Oak St.  It is open for lunch and dinner 7 days a week.  Click here for more information. 

More Cupcakes is located at 1 E. Delaware St.  It is open 7 days a week from 10am – 8pm.  Click here for more information.

In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and take the CTA Red Line or the #3 bus to Fig & Olive and More Cupcakes.  Save on gas.  Avoid traffic, road rage and parking.  Reduce pollution. Don’t drink and drive!