Chicago 

EAT

Cindy’s Rooftop: located in the Chicago Athletic Association Hotel, this is a must, ideal for a nice sunny day but the views of the "bean” will be good regardless, great for brunch, make reservations if you can, otherwise get there early!

Monteverde: great Italian food, so many fresh made pastas, good ambience with some great artwork. I would have happily eaten here every night if we had discovered it sooner.

Au Cheval: the spot for burgers, upscale diner, unassuming location but the food was unreal, be prepared to wait but there are lots of nearby spots for drinks.

Girl & the Goat: dinner spot, definitely need reservations, don’t miss this one! Executive chef (and co-owner) Stephanie Izard was the first female to win Top Chef. She has two other restaurants that I’m sure are worth checking out… Little Goat and Duck Duck Goat.

Fulton Market Kitchen: dinner spot, located in an old warehouse, very unique space.

DRINKS

Three Dots and a Dash: by far my favourite spot for drinks, this tiki bar has the best drink list full of creative cocktails all served in unique glasses.

Cerise Rooftop Bar: at the Virgin Hotel, rooftop bar with views of the cityscape.

DO

Chicago Cubs: go see a game at the famous Wrigley Field, it’s a short train ride away from downtown, great atmosphere at and around the field, all of the nearby homes turn into little parties and get togethers of people watching from their patios and rooftops.

Architectural River Tour: about 90 minutes long, they take you along the rivers and you get to see most of the famous buildings, really unique perspective seeing such big/tall buildings from the water, it can get quite hot out on the deck if it’s sunny.

Cloud Gate (the “bean”): stop by and see the bean! We were lucky enough to show up just after a thunderstorm and the whole area was blocked off so we got an unobstructed view.