Some say romance is a matter of perspective, though it never hurts to use inspiration. With Chicago’s wealth of scenery, street festivals, fine dining and quiet, corner hideaways, it’s a city perfect for kindling romance—new and old alike.


Whether you’re planning an evening, a day or a weekend of romance in the Second City, a good place to start is with an activity. Simple works best; nothing assuming or demanding. The iO Theater in Wrigleyville often has different improv shows, sketch comedies and one-man shows that can work as a good way to break the ice. Alternately, the Chicago Opera Theater can provide some timeless and sentimental entertainment. There’s always the Shedd Aquarium, on the lake, which can be both mesmerizing and contemplative.

Perhaps more important than the entertainment is the food. Certain quieter neighborhoods, such as Lincoln Park, Lincoln Square, or the West Loop have restaurants and lounges that cater to the starry-eyed. A restaurant like Prairie Fire in the West Loop provides mid-range comfort food that won’t weigh on your stomach, and they have an excellent wine menu to boot. A BYOB place, such as Pizza Art in Lincoln Square, pairs a more frugal option with inimitable Italian-style pizza and pasta.

During the warmer months, you might also want to take a lakeside cruise with the services offered by companies such as Spirit of Chicago. You can also take a ride on the Ferris wheel on Navy Pier and look at the city lights at night (nothing beats a view like that).

If you’re on a romantic getaway to Chicago, a few nights at the Drake Hotel, or the Palmer House will be memorable. Many of these hotels are filled with history, and rather than just acting as a background piece, they can become part of your story.