7 Romantic Things to Do in Chicago

With fall on the way, now is the time to plan a romantic getaway with your sweetheart—the weather will be perfect for evening cuddling in soft sweaters or walking hand in hand in the crisp autumn air. Believe it or not, Chicago is a surprisingly romantic place for lovebirds, despite the hustle and bustle of the Windy City. It’s full of luxurious hotels and charming bed & breakfasts, as well as intimate restaurants to share an elegant meal. Plus, you’ll make unforgettable memories while experiencing the multitude of attractions Chicago offers. Picture yourself cozying up to your mate as you take in the spectacular Chicago skyline while the sun sets. If that’s not romantic, what is?

Need some help thinking of romantic things to do in Chicago? Here are 7 suggestions for you and your loved one to enjoy.

1. Ferris Wheel at Navy Pier

Ferris Wheel at Navy Pier

There will be plenty of snuggling opportunities at the top!

This 15-story Ferris wheel is located at one of the most visited attractions in Chicago, the Navy Pier. From the top of the famous Ferris wheel, you and your partner will escape the crowd for a few minutes for some alone time with the scenic skyline and Lake Michigan views. After you depart the Ferris wheel, Navy Pier is a lakeside wonderland to explore. You’ll find romantic restaurants, shops, and other top-class attractions as you stroll along with your loved one.

2. Skydeck Chicago (top of Willis Tower)

Looking out from the observation deck at the top of the Willis Tower (formerly Sears Tower) is one of the most romantic things to do in Chicago. You’ll enjoy 360-degree views from the tallest tower in the northern hemisphere, literally taking your love to new heights. For the most romantic view, head to the Skydeck observation tower at sunset or after dark when the city lights are glowing.

3. Horse Drawn Carriage Tour

This one’s for the lovebirds looking for classic old-fashioned romance. One of the most unique and memorable ways to see Chicago is by horse-drawn carriage. Many of the carriage rides in Chicago will take you right along the lovely shores of Lake Michigan. There are quite a few carriage companies in Chicago to choose from, some of which even offer antique carriages and vintage-dressed drivers. Most carriage rides are also offered in all four seasons.

4. Buckingham Fountain in Grant Park

Buckingham Fountain in Grant Park

It even looks romantic in black and white.

One of the largest fountains in the world, this centerpiece in Grant Park shoots out 1.5 million gallons of water from 134 jets. The fountain features choreographed displays of water, music, and mystical lights that take place every hour on the hour, lasting about 20 minutes. The show is certainly a sight to behold. End a romantic evening walk through Grant Park with this one-of-a-kind finale.

5. The Signature Lounge, 96th Floor, John Hancock Center

Located atop the well-known John Hancock Center you’ll find the romantic restaurant and cocktail bar known as The Signature Lounge. The view from the 96th floor is phenomenal (to say the least), and the food and drink are equally exquisite. This is the perfect spot to wind down after a busy day or get geared up for a romantic evening out.

6. The Art Institute of Chicago

The Art Institute of Chicago

Art gazing is one of the top things to do on a date.

Whether you and your mate are into art or not, the Art Institute of Chicago is a must-see attractions for everyone. Not only is it one of the top art museums in the world, you’ll get lost in a daze of romance and mystique as you wander through the endless hallways containing works of art from around the world that span centuries. To up the romance factor, avoid busy, touristy times, and opt to visit the museum on a weekday in late afternoon.

7. Cruise on Lake Michigan

There may be no activity more romantic than a cruise along the dazzling waters of Lake Michigan while you eye celebrated architecture and the extraordinary Chicago skyline. Cruise companies offer options for everyone, whether you’re looking for an intimate dinner cruise, an enlightening historic tour, or a brisk brunch sail. No matter what you decide on, Chicago lake cruises are a guaranteed good time.


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