Romantic Things to Do in Chicago

January 22, 2013 by

Things to Do

Chicago, like most major cities, offers a wealth of options for things to do, whether you’re traveling with kids or looking to spend time with someone special. If you’re looking for romantic things to do in the Windy City, you’ll have your pick of great activities to suit a range of styles, budgets, and interests. To get you started, check out these romantic things to do in Chicago.

Drinks with a view

There are dozens of great rooftop bars in Chicago (most located on top of hotels) but there’s no better place for taking in the view than the Signature Lounge on the 96th floor of the John Hancock Building. There’s no admission fee (though the lines can be long on weekends and summer nights) so for the cost of a cocktail you can watch the sun set or the stars shine through floor to ceiling windows 96 floors above  the city.

View from the Hancock photo courtesy of rebecca anne on Flickr

View from the Hancock photo courtesy of rebecca anne on Flickr

Romantic dinners

Chicago is a foodie paradise with plenty of great restaurants that specialize in serving amazing food in a romantic atmosphere. Tru, Alinea, Les Nomads and L2O are among the most notable, but there are options for just about any budget or appetite. Tango Sur, HB, and Mon Ami Gabi offer excellent food and candlelit ambiance at a lower price point.

Getting around in style

For a romantic ride around the city, head to Michigan Avenue and hop in a horse-drawn carriage. Rides are available all year round (with blankets provided for winter rides) and start at around $50 for a 30-minute ride down quiet side streets where the only sound will be the clip-clop of the horses’ hooves on the pavement.

In warmer months, you can cruise Lake Michigan on a sunset, dinner, brunch, or lunch cruise. Many offer live music and dancing and all offer spectacular views of the city skyline from the water. Or for a real splurge, see Chicago from the air on a private helicopter tour high over the city.

Check out Lake Michigan cruises in Chicago or helicopter tours over Chicago 

Picnic in the park

Relax in some of Chicago’s green spaces. Pack a picnic and head to Lincoln Park and Millennium Park, find a spot away from the crowds, and enjoy. There are also 26 miles of shoreline in Chicago, so if you’re visit falls in summer, you can opt for a day at the beach instead.

Listen to live music 

Venues all around Chicago offer live music and you can find a jazz or blues performance scheduled for just about any night of the week. One of the city’s most iconic clubs is the Green Mill, which has been offering nightly live jazz since the 1930′s. Other options include Kingston Mines and Buddy Guy’s.

Learn more on a blues tour of Chicago

- Katie Hammel

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