Enjoy a cocktail at the bar where we had our first date.
Arguably our favorite restaurant in Chicago. Plan ahead - reservations need to be booked a month in advance & fill up very quickly.
A boat ride on the Chicago River & Lake Michigan learning about Chicago's renown architecture.
Amazing rooftop brunch with views of the Magnificent Mile.
The Art Institute of Chicago holds the largest collection of Monet's in the world outside of Paris.
The casual counterpart to Smyth. Fantastic burger.
An old school Italian restaurant that's a Chicago institution. Reservations are recommended as this restaurant is small. Stop at Richard's, the bar next door, for a blast from the past (warning: you will leave smelling like cigarette smoke).
Another Chicago institution - this breakfast spot marks the start of Route 66.
The site of one of our first dates. This museum is very manageable for a quick visit & it's right off the lakefront trail.
Rooftop bar and restaurant with unparalleled views of Millennium Park, Grant Park, and Lake Michigan. Very close to the Pendry & Chicago Cultural Center.
This is the place to go for traditional Chicago deep dish.
Good sushi. Fun vibes. Located in the heart of West Loop.
Grab an Italian beef at the restaurant that is the subject of the Emmy award-winning show, The Bear.
See a comedy show!