Travel Diary: Chicago


I spent Labor Day Weekend in the Windy City, and naturally ate and drank my way through town! Read on for some of my favorite restaurants & activities!!

Millennium Park

A trip to Millennium Park is obligatory when in Chicago! The Buckingham Fountains and the famous “Bean” are must-dos every time I’m in Chicago, and are always worth it for the amazing photo ops!


The Signature Room at the top of the Hancock Tower

Love the Signature Lounge, because it’s free to get to the top of the Hancock! Instead of paying $20 to go to the observatory deck, you can go to the bar level and spend that money on delicious mojitos and snacks!! Eat and drink while enjoying breathtaking views of the city.


The Purple Pig

This place is wine / cheese / cold cut heaven! It took us two hours to get a table for seven (beware: the restaurant doesn’t accept reservations!). There’s a cute patio where you can wait, so be prepared to grab a bottle of wine and enjoy the ambience!



Eataly is a combination of Costco and Italy. If you’ve ever been to Italy, you walk into Eataly and realize that it’s a much cleaner, more organized version of every Italian street market! There are various restaurants, shops, and wine / cheese / meat stations throughout the two-story Costco-like warehouse. Basically, it’s the best place ever!! (DOUBLE BONUSES – It’s just down the street from TopShop ANDDDD you can finish your night at the Nutella station!!!) 


The RIver Boat Tours

We did the Architectural River Boat Tour, which is a 75 minute tour on the river that explains the history of Chicago through it’s impressive architecture! No matter the time of day, it’s lovely to sit atop the boat, sip some vino, and enjoy the sunshine and the breezes of Lake Michigan!


Wrigley Field

Historic Wrigley Field is worth a visit, even if you can’t get tickets to a game! We sat outside at a bar across the street and cheered with the stands every time there was a homer!! Such a fun part of town, it’s hard NOT to be a bandwagon Cubs fan!


Pequod’s Deep Dish Pizza

You can’t leave Chicago without eating deep dish (at least a few times!). Pequod’s is the best because they — GASP — never wash their skillets. That’s right, they wipe their pans down but they never wash them! This creates a deliciously sweet caramelized layer on the crust.  The sweet + savory combo is unreal and way too delicious.


Suffice it to say that my trip to Chicago was a foodie experience. When combined with lots of vino and my very best friends, the city has become one of my favorites! (Just don’t bring this Cali girl there in the Winter, PLEASE!!).

What sites did I miss in the Windy City??! Share below!