The 10 Most Romantic Spots in Chicago

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Chicago, a city known for its rugged neighborhoods, deep-dish pizza and of course, brutal 50-mph winds… doesn’t lack in character or culture. However, there’s a softer side to Chicago that they don’t show you on the big screen. Whether you’re looking to surprise your significant other on an anniversary or want to impress a first-date, these are 10 of the most romantic spots in the Chicago area.

Dîner en Blanc

Dîner en Blanc is an immersive experience that turns some of Chicago’s most beautiful public spaces into a chic rendezvous for over 1,000 invited guests. Head-to-toe in all white garb, the Dîner En Blanc attendees can enjoy their dinner, mingle with the eclectic crowd and reminisce on the prestige of high French society. This is a date-night for the books.

Chicago River Walk

Whether you take on the river walk by boat or foot, you will feel the true magic and energy of the city. This romantic escape from the hustle and bustle of downtown is all you need on a crisp Chicago evening.


Most date nights include a stop at the local cocktail bar. But what if hangovers aren’t really your thing? Head to Tropikava and try a relaxing, non-alcoholic, non-addictive elixir by the name of Kava. This drink derives from the Kava root and has long been used socially and ceremonially in the South Pacific. Kava is said to induce clarity, relief from anxiety, and a calm sense of euphoria. Elevate to another state and relax with your partner at this innovative juice bar.

 Millenium Park

You’ve seen the iconic images of Millennium Park and its prominent artwork on TV shows, movies and popular Instagram feeds. But this expansive civic center has much more to offer than meets the eye. Watch a movie under the stars, buy tickets to one of the colorful concert series or sneak away for a private picnic.

 Franklin Park Conservatory & Botanical Gardens

Nothing says romance like a walk through vivid displays of flora and fauna. You’ll find captivating experiences at the conservatory that stretch far beyond the flowers. Sign up for one of the conservatory’s cooking classes and fall in love with the art of creating culinary classics from scratch. Make pasta, collect herbs, perfect Chinese recipes or even learn how to make holiday jams. Just make sure you make it out in time to see the sunset over the conservatory’s greenhouse.

 Promontory Point

Most travelers overlook this breathtaking lookout point, which makes it the ideal spot for those who are willing to venture off the beaten path. Grab your loved one, pack a light lunch and take a stroll along this peninsula of Lake Michigan.

 The Signature Lounge at the 96th

Enjoy a cocktail above the clouds as the Chicago cityscape leaves you completely bewildered. The Signature Room at 96th is placed 96 floors above the ground and offers a slew of perfectly crafted cocktails from a team of world-class mixologists. Watch the sunset, order a few small-bites for the table and enjoy the timeless ambiance.

 The Chicago Theatre

The emblematic lights in the windy city do not shine any brighter than when you’re underneath the marquee at the Chicago Theatre. Catch a show and marvel at the French Baroque-style architecture that was designed in 1921. It is the essence of sentimental charm.

 North Pond

North Pond was originally built as a warming shelter for ice skaters back in 1912. Since then this spot has evolved into a wholesome restaurant with seasonal, locally sourced products and at atmosphere that is true to the culture of arts and crafts. Located in Lincoln Park, this restaurant is adorned with floor to ceiling glass windows that are especially dazzling at dusk.

 Green Mill Cocktail Lounge

Nothing sets the mood quite like the melodic tones of live music. The Green Mill was frequented by legendary popular figures and continues to amaze crowds looking to kick-back and unwind with an ongoing jazz soundtrack.


  As a Las Vegas native with an affinity for global excursions, Perri left the United States for love, self-discovery, and amazing European pastries. This lucky girl hasn’t stopped traveling since. You can check her out her latest adventures at her Instagram @princeandthepear. 


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