For a memorable weekend that makes it easy remember all the reasons you fell in love with your spouse or ignite a simmering new connection, plan a whimsical few days in a nearby big city. An easy drive for folks in the Midwest, Chicago is chock-full of glamorous hotels, unexpected entertainment, great food and adventurous things to do.
Here are five of my favorite offbeat date ideas in Chicago:
Fly through the Night
Whether you live in Chicago, visit for fun or are planning an inaugural trip, there may be no better way to see the city with your sweetheart than by air — alone. Take a half-hour helicopter ride over the Windy City at night and get a whole new view of its most famous landmarks, including Wrigley Field and Navy Pier. You’ll feel like you’re on The Bachelor when you snuggle up and enjoy this memorable private tour of Chicago. Expect your pilot to point out hotspots and give you the inside scoop on the city. Several operators offer sunset and evening helicopter rides, including options that depart from Chicago Midway Airport. Consult your trusted travel resources and find a company that meets your needs.
Paddle the River
Few things are more romantic than embarking on an outdoor adventure with someone special and taking in an iconic vista that few others experience. That’s why it’s so great to get away from the crowds of Chicago and enjoy a few hours alone with your date on the Chicago River. Rent a tandem kayak from Urban Kayaks and take a self-guided trip down the Chicago River. You can board the kayak in Chinatown and paddle to the downtown location for a one-way experience or commit yourself to the full round trip. Kayaking in the middle of the city will provide great fodder for stories to share in the years to come.
Explore Local Foods
Avoid the where-should-we-eat stress and just go enjoy the Gold Coast & Old Town Food Tour by Chicago Food Planet Food Tours. This well-loved three-hour walking tour gives you a chance to sample signature dishes and drinks from off-the-beaten-path local restaurants in these popular Near North neighborhoods. You’ll also get insider information on the history, architecture, attractions and other offerings of Chicago’s most famous communities. Chicago Food Planet also offers a Chinatown Food Tour and a Bucktown & Wicker Park Tour. All three tours are available daily from 11 a.m. until early afternoon from March through November.
Laughter and humor is a timeless antidote to stress, boredom and conflict. And there may be no better place in all of Chicago to laugh than The Second City, an iconic Old Town comedy club specializing in sketch comedy and improv. Find a show on any night of the week; late-night shows begin at 11 p.m. on Fridays and Saturdays. For a total experience, book a Dinner/Show package through The Second City Box office at 312-337-3992; this package offers a special menu and pricing at one of the theater’s partner restaurants as well as preferred seating at the show. If you decide to forego the dinner package, don’t worry; full bar service and appetizers are also available at the theater throughout the show.
Chill with the Blues
Does anything say romance more than a crowded dive blues bar that oozes character and world-class music talent? Exactly. Chicago is the birthplace of what’s known as urban blues, a spin on classic blues that’s infused with jazz and deep bass. Muddy Waters and Buddy Guy are well known for performing this type of music, and The New York Times named Rosa’s Lounge the best blues bar in Chicago. You’re practically obliged to check it out when you’re in the city, so it’s a good thing that the place features live Chicago blues music every night of the week. Rosa’s is located on Chicago’s near Northside.