Romantic Things to Do In Chicago

chicagokissChicago may not immediately appear to be a romantic city. It’s big, loud, and busy. El trains clatter on the overhead tracks, taxis sit in traffic, and workers rush and to and from offices and commuter trains. But amidst the hustle and bustle of the city, there are plenty of opportunities for romance. Here are some of the most romantic things to do in Chicago.

Drinks at the Signature Lounge at the Top of the Hancock Building
There’s no doubt that the secret is out when it comes to the Signature Lounge on the 96th floor of the John Hancock Building in downtown Chicago. On weekend nights from sunset through the evening, there are long lines for the elevator and at least a 20-minute wait for a table with a view. Despite the crowds, this is one of the city’s most romantic spots. Enjoy a cocktail and share an  appetizer with your loved one as you watch the sun set over Chicago or view the city’s twinkling skyline at night.

Just below the lounge, on the 95th floor, the Signature Room restaurant serves brunch, lunch and dinner, but like many restaurants of its kind, the views can be better than the food.

horseA Carriage Ride Down Michigan Avenue
A little cheesy? Maybe.  But a cuddling with your sweetie in a carriage as it gently rolls past the lights of Michigan Avenue is undeniably romantic. Rides take place all year round, in anything but extreme cold, heat, snow or rain and can last from 30-60 minutes and cost $45-$100 for up to four people. Rides can be pre-paid or arranged with one of the carriages that stop around Michigan Ave. and Chicago Ave.

An Unforgettable Meal
There’s no shortage of romantic restaurants in Chicago, many of which can cost a week’s salary. Restaurants like L2O, Tru, Alinea,  and Les Nomades are known across the country for their inventive cuisine, celebrity chefs, and luxurious ambiance. A reservation at one of these places is hard to get (you’ll need to plan several weeks in advance in some cases) but will ensure a meal you’ll never forget.

Luckily, there are some less-expensive options as well, thanks in part to Chicago’s BYOB law. Certain restaurants allow guests to bring a bottle or two of their own wine for a small corkage fee (usually $2-3 per bottle), which can help cut down on the overall cost. Many of these BYOB restaurants are more informal, but there are a few that marry upscale ambiance with the ability to bring your own booze. Bonsoiree, HB, and Schwa all feature haute cuisine, a romantic atmosphere and superb service, but allow guests to bring their own wine.

A Stroll Along the Lake or Through Lincoln Park

Chicago has no shortage of beautiful skyline views. One of the most romantic spots to see the city from is along the Lakefront path. During early evening you’ll be sharing the path with joggers, walkers, and bikers, but once the sun sets, you’ll find yourself virtually alone with your companion as the lights of the city’s buildings shine in the distance.

During the day and early evening, Lincoln Park is the perfect lover’s retreat. Wander through the free Lincoln Park Zoo, stroll around the North Pond (or dine at the locally-sourced American restaurant of the same name), shop for fresh produce at the summer Green City Farmers Market, or find a secluded spot to enjoy an outdoor picnic.

Spend a Day at the Museum
Chicago’s many museums may be filled with kids and families on weekends, but oftentimes during the week, they’ll be nearly empty. Discuss the meaning of art or the love-life of a famous painter and then steal kisses in empty exhibit halls. Downtown, choose from the Art Institute, the Shedd Aquarium, the Field Museum, the Adler Planetarium or the Museum of Science and Industry.

greenmillListen to Jazz
Chicago has a proud history of jazz and blues music, and there are multiple venues that offer live music several days a week. One of the most famous and popular is the Green Mill jazz club, located in Andersonville, about 20 minutes north of the Loop.

The Green Mill has been around for over 100 years, and has been offering nightly live jazz since the 1930’s. The place practically drips with history, and both the performers and the audience clearly love and appreciate the music. During sets the room goes silent except for the sultry jazz tunes so its an ideal place for those who would rather cuddle than chat. The Green Mill website lists the schedule of performances.

Photos by jill d; digging90650; rebecca ann