Weekend in the Windy City

We have an itch for traveling. One that can never be satisfied.

When the opportunity arose to take a spontaneous trip to wherever our hearts desired (within the continental U.S.), we had quite a time choosing where to go. Deciding against somewhere on the west coast, we knew it had to be close enough to take advantage of a long weekend. We remembered how much fun it was when we were younger and surprised our cousins when we arrived at their doorstep unannounced. So, we decided to surprise one of our dearest friends. We made a quick call to her mother, to see if she was going to be in the city that weekend (She is quite the world traveler as well), and then booked our flights!

We took the redeye from San Francisco, leaving the lovely 70 degree weather we were having and landed in Chicago, for what was forecasted to be a typical February Chicago weekend. (It turned out lovely). 

Operation Surprise M.

Once we landed in Chicago, We drove straight to M's office for the big surprise. She had NO idea we were coming so when the office receptionist asked her to come to the lobby, she thought she was in big trouble. Surprising people is one of our favorite things and seeing M's face was priceless! 

Afterwards, we let M recover from the surprise and we headed to our abode for the weekend in the Gold Coast. 

Once we freshened up from our long journey, we knew our first stop had to be....Lou Malnati's 

A Chicago icon, Lou's has served up deliciously food-coma inducing deep dish pizza since the 1940's. Eve lived in Chicago for 6 months back in 2014 and developed quite the affinity for "The Lou" which features: Spinach mix, mushrooms and sliced tomatoes, all covered with mozzarella, romano, and cheddar cheese. YUM!

Naturally, to start off the mini-holiday on the right foot, we washed it down with a bottle of bubbly!

To walk off the pizza pounds, we wandered down Rush Street to window shop and make our way to Michigan Avenue.  

Michigan Ave. (The Magnificant Mile) is the shopping and tourist mecca of Chicago. There is literally every store imaginable on this 13 block stretch. 

Our top picks are: 

  • Uniqlo- Great basics and the Starbucks on the 6th floor has AWESOME views of Michigan Ave. (pictured above)
  • Topshop- Can't get enough of this UK brand
  • Garrett Popcorn- Get the Cheddar/Caramel combo
  • American Girl Place-To live out your childhood dreams

After M got off work, we met up for more bubbles before heading off to celebrate a friend's birthday. 

Day two, began with brunch at the Pump Room, in the Public Hotel. Without a doubt, this is our favorite place for the casual yet glam pre- dinner drink. Eve's usual is the Passion Chili cocktail and Truffle Flat Bread. In Chicago's golden years, this was the spot to see or be seen (check out all the photos as you venture to powder your nose in the Ladies). 

We naturally started with mimosas. After a long debate over what delicious dishes to order, we decided on the Challah French Toast and Whole Wheat Wild Mushroom and Farm Egg Flatbread. We were NOT disappointed. Cheers!!

Afterwards, it was straight to pedicures at Polish and Pour! This spot is perfect for a bit of girlfriend pampering. With a full bar and Sex and the City playing continuously, there is no way you can't enjoy yourself! 


Post pampering, we transported ourselves to the wonderful land of Eataly. This two floor Italian food market has LITERALLY everything Italian under the sun. We ogled at the cheese shop, marveled at the Nutella bar, but settled ourselves down for some oysters and a fresh burrata cheese plater. This burrata is made in-house daily and WOW, can you taste it! 

Once home, we rested before heading out for drinks at the newly renovated Chicago Athletic Association. A Former 1890's men's club, this place is THE spot for downtown night life. We headed straight for the Game Room which features billiards, bocce ball, shuffleboard, and more. M had one of their Highballs and we started off with their cava. 

Next up was the library-esque lobby lounge for some more refined French sparkling wine while we waited for our friends K and J to arrive. This was our favorite place at the CAA as it was quieter and gave off a sophisticated yet laid-back vibe. Once we were all together, we headed to Cindy's the rooftop restaurant and bar for more bubbles, cocktails, and a fabulous view of the Bean and its surroundings. 


Day three, we recovered from our slight over-indulgences with naturally, MORE food and drinks! Eve's favorite brunch spot, Bub City is a Country Western restaurant and bar featuring live music on Sundays and an out of this world Bloody Mary bar. Ten bucks gives you a poker chip which you cash in for a visit to the Bloody Mary bar. These babies can be a meal in themselves if you know how to make them right (Yes, that is a grilled cheese with an American Flag). 

We had one last stop before heading home, Sprinkles ATM. Open 24/7 it spits out the most delicious cupcakes in America. We snagged a Red Velvet and Salted Caramel for the road. Best idea ever!

After rolling ourselves home, we packed up, said our goodbyes, and headed home after a fun filled weekend in the Windy City!


Ivy & Eve