It’s been called “New York done right,” but most locals would argue Chicago, the third largest city in the United States, can stand on its own as a distinct metropolis.
Make your date guffaw and check out world-famous The Second City or i O Chicago Theater.
The Old Town School of Folk Music has an open house on the first Friday of every month.
Bring your date and an instrument (or dancing shoes) or just sip drinks while taking in the sounds of the community.
Guide to Dating in Chicago: Get Artsy Learning is sexy.
Picnic at the 57-acre Museum Campus in Grant Park, then wander through one of the three museums on the property: the Adler Planetarium, the Shedd Aquarium or the Field Museum of Natural History.