Posted Feb 9, 2015

Most Romantic Destinations in Chicago

Paris might be considered the City of Love, but Chicago can give it a run for its money. That’s right, the Windy City is ripe with romantic destinations, you just have to know where to look.

Most Romantic Destinations in Chicago

Us Chicagoans have experienced the charm of our city, from its stunning architecture to its parks, beaches and hidden nooks. So here’s some advice from a native on where to spend your weekend getaway or day trip with your significant other:

Millennium Park

While Grant Park has been around longer than Millennium Park, the newer locale has the ambiance of an established retreat. It’s also full of things to do and see. For instance, the outdoor concert hall regularly hosts shows you can attend with your loved one– my boyfriend and I saw an orchestra perform once. We got to sit on the lawn with a blanket and eat snacks out of our picnic basket. It was the quintessential cute day trip with the added bonus of live music.

Most Romantic Destinations in Chicago - Millennium Park

What’s more, Millennium Park transforms into a romantic haven come winter- that’s right, winter. What once was the site of an outdoor bar and grill during the warm months transforms into a skating rink when temperatures drop. You can rent ice skates and glide with your significant other’s hand in yours  (aww).

The famous statue Cloud Gate, called The Bean by locals, is on a platform that overlooks the ice. My boyfriend and I stood on the platform in the snow (you know, the big, pretty kind of flakes), watching other couples skate. The lights from nearby posts gave the whole park a soft glow– I’m getting giddy just picturing it!

Navy Pier

Navy Pier juts out into Lake Michigan and is full of attractions. The front end has plenty of restaurants where you and your honey can dine. You’ll also find a movie theater, a Children’s Museum, the Chicago Shakespeare Theater (they put on some seriously amazing work) and, of course, the famed Ferris wheel.

Most Romantic Destinations in Chicago - Navy Pier

I suggest seeing a play– avoid things like “Macbeth” and go for a romance like “Taming of the Shrew” instead – then hop on the Ferris wheel. While you’re peering at the lights of the Chicago skyline from high up, you’ll have the opportune moment to plant a smooch.

Carriage Rides

Want to see more of the city? Grab your loved one and hop on a carriage. Chicago Horse and Carriage offers love-struck couples a classic, romantic trip around the city via horse-drawn carriage. You’ll feel like Cinderella and her prince marching by Millennium Park, Buckingham or Lincoln Park.

Most Romantic Destinations in Chicago - Carriage Rides

Taking a ride is a great option after a meal when you want to make room for dessert. The two of you can cuddle up together and enjoy the Chicago view.

Chicago Botanic Garden

The Chicago Botanic Garden is north of the city, but it’s worth the drive or train ride to visit. With a multitude of gardens and plenty of ground to cover, you and your loved one can wind your way through flower beds galore.

Most Romantic Destinations in Chicago - Botanic Garden

My favorite area is the Japanese Garden– with beautiful cherry blossom trees and sand gardens, you’ll be in a tranquil environment while enjoying the company of your partner.

What’s more, the Chicago Botanical Garden is open for event rental and often hosts weddings– hint, hint. After using the garden as a romantic destination, you can come back for your I do’s.


Chicago is home to a ton of well-known museums, including the Adler Planetarium, the Field Museum, the Shedd Aquarium, the Chicago Art Institute and the Museum of Science and Industry. Each contain interesting and educational exhibits you can explore with your loved one in tow.

Full Moon Over Adler Planetarium

I love the Adler Planetarium. Every time I go, my mind is blown by the vastness and complexity of space. It’s even more fun to see with my boyfriend, who shares a similar interest in the topic. We can watch shows about the stars in the Definiti Space Theater, a domed room that projects a 180 degree view of the cosmos.

Improv Shows

Chicago is a big theater town, and it’s best known in the industry for its improv. From iO to ComedySportz, the city has plenty of well-known theaters where skilled comedians make up sketches on the spot. Second City, which tends to funnel many performers to “Saturday Night Live” is also downtown.

Most Romantic Destinations in Chicago - Improv Shows

If you and your significant other want to start your day trip with some good laughs, see an improv show. It’s the perfect way to get topics of conversation for a meal you’ll have afterward – “I can’t believe he did that!” Many improv theaters have bars, so you can enjoy a few cocktails while watching the show.

A word of advice from a Chicago native with an improv background– you’ll have more fun if you participate. Shout suggestions when the actors ask, and raise your hand if the performers want someone from the audience to join a skit.

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Most Romantic Destinations in Chicago

Photo Credit: Jo Ann DeasyJustin KernMr. NixterMarty GabelJanetandPhilChris SmithPat & Keri

Jen Jackowski


Jen Jackowski is a graduate of Illinois State University, where she studied theater and English. Her experiences in the theatrical arts left her with a love for storytelling that she breathes into her writing. She’s also passionate about art, gaming, sustainability and fashion. Her work has been published in the literary magazine, Euphemism.

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