Chicago

COFFEE 

Limitless Coffee : different latte choices you don’t see everywhere / great drip dark brew & great avocado toast
Heritage Bike & Coffee : awesome lavender latte 
Elaine’s Coffee Call
Goddess baker
Big Shoulder Coffee : Cute and TINY shop. Great place for a grab and go coffee or just to sit for a little while. seating is limited outside. Their iced latte is terrific and people rave about their Marshmellow Latte
CCferns Chicago
Our fairgrounds : they have a Brew Bar where you can pick three for a flight, or get a full cup of your favorite coffee 
Sawada coffee

FOOD 

*Breatrix : have to go for brunch!! My recommendation is the Cauliflower Grits & Eggs or Quinoa Cakes W/ Poached Eggs
Gino’s East : deep dish pizza
*Lou Malnati's Pizzeria : deep dish pizza (the best in my opinion )
Giordano’s : deep dish pizza
Uno’s Pizzeria & Grill :  Chicago's first deep dish pizza restaurant 
Portillo’s : famous for the Italian beef / hotdogs
Uptown Pho : it was a cold day and we were craving soup. some of the best Pho I have had
Eataly
*Jeni’s : best ice cream in the world / dairy free options
Cindy’s rooftop: great restaurant, brunch + view of the bean
Food by Fare
Farmhouse Chicago 
Emma
Federales : Mexican / order a shot in a ice shot glass then throw it at the wall
Wrigleyville : bar scene around wrigley field
Stan’s Donuts
Little Beet Table
Pacific Standard Time​
Honey Butter Fried Chicken 
Hampton
Café Babareeba

BARS 

Bub City : awesome live music / have food as well
Fados
The Laurel Room : Coastal California fare meets Chicago summertime
Blue Chicago : fantastic jazz music
Happy camper
Parlor pizza
​Offshore 
Three dots and a Dash

ACTIVITIES 

Buckingham Fountain
Drinks/brunch at Cindy’s on the rooftop overlooking the bean
Millenium park : the famous Chicago bean is located here
Bar hoping around wrigleyville
Take the L (CTA train) at least once for a full Chicago experience
The Lincoln Park zoo : completely free
Navy Pier
Willis tower sky deck: views of the entire city
Revolution Brewery
Goose Island Brewery
Architecture boat tour 
Walk down Michigan Ave : shopping along the way
Take a water taxi on the river
Riverwalk : walk along the river for awesome views! 
City Winery Chicago on the Riverwalk : sit outside and enjoy a bottle of wine while people watching
Lakefront bike trail : run, walk or rent a bike