6 Romantic Chicago Date Ideas

In Step With Barack and Michelle in Hyde Park

The love story of Barack and Michelle Obama started in Chicago's Hyde Park neighborhood and grew all the way to the White House. Gain inspiration for your own romance by walking through the neighborhood where the two-term president dreamed of goals that led him to the Oval Office and the woman who became his First Lady. You'll walk by the places Obama lived, his barber shop and the couple's home on the tour. Afterward, have lunch at Medici on 57th, a casual place where the couple and their girls dined out in the years before they moved to the nation's capital.

Sail Away With Me on a Chicago Boat Tour

Getting a new perspective is always good for a healthy relationship—and for sightseeing. Aboard a Lake Michigan cruise ship, you'll see Chicago from a new angle. It's a good excuse for a little refresher on love, too, with a glass of champagne, a beautiful meal and music playing in the background. The Odyssey and the Mystic Blue cruise ships depart from and return to Navy Pier with several sailings a day. Choose a brunch, lunch or dinner cruise to suit your mood and leave you ample time to spend together on your escape to Chicagoland.

Hand Holding in Maggie Daley Park

You can't get more romantic than a walk in the park with a breeze in your hair and a special someone to kiss. Chicago's scenic lakefront parks are perfect for your outing, but if you slip away to the northern most part of the vast greenway you'll find the Cancer Survivor's Garden in Maggie Daley Park. The beautifully manicured garden with its pavilion and granite columns has become one of the city's top spots for outdoor weddings, so you know that romance is in the air. Nearby, in the more public part of the park, you can ice skate with your sweetheart in the winter and play mini golf and picnic in the summer.

A 360 View of Chicago at the Signature Room

If you want to skip the long lines of tourists waiting to get to the observation deck at the 360 Chicago building, just walk right into the building and take the elevator to the Signature Room and Lounge. You'll save on the ticket, but that's offset by the price of the drinks and menu items. You'll also be one floor higher than the observation room and the Lounge is far less crowded, so you'll be able to whisper sweet nothings to your partner and be heard. Time your visit so you can get seats on the west side of the building to watch the sun set and the lights come on all across the city.

Chicago's Carriage Ride Charm

The gentle sway of a horse-drawn carriage and the clip clop of hooves seem to invite snuggling. When it comes to romantic things to do in Chicago, this is one of the finest, particularly when it's paired with seeing some of the most beautiful sites the city has to offer. Both Chicago Horse & Carriage and Great Lakes Horse & Carriage offer rides through the parks and historic neighborhoods. The drivers can accommodate various times, and pick-up and drop-off sites for your convenience. Just don't plan on riding between 4 and 6 p.m. on Monday through Friday, as the horses are kept off the streets then to avoid rush hour traffic.