Romantic Things To Do in Chicago

Believe it or not, Chicago has been a low-key mecca of romance for generations now. Just think about it: some of the most romantic modern classic films are set here. Who could forget the amazing skyline backdrops in About Last Night? Chicago is practically its own character in My Best Friend’s Wedding. And let’s not forget pretty much every teenage, heartthrob-laden John Hughes movie is set somewhere in the Chicago suburbs (shoutout Highland Park). 

Chicago has something for the romantic in all of us – art, music, and history swirl around the city’s sparkling skyline, amazing restaurants, and beautiful gardens. 

Whether you’re visiting or you call Chicago home, if you’re looking for something to do with your sweetheart in ChiTown, check out the following list for a bunch of great spots to hold hands, cuddle up, and maybe steal a smooch.

Romantic Date Ideas & Things To Do In Chicago

1. The Art Institute of Chicago

This world-renowned museum has one of the country’s most celebrated collections of historic and contemporary fine art, including famous works like Edward Hopper’s “Nighthawks,” Seurat’s “A Sunday Afternoon…” and about 300,000 more.

Why this is a romantic thing to do: When the weather is too hot, too cold, too rainy or windy, spend your romantic day among the masters and hold your significant other close while exploring stunning art.

Go to the Art Institute’s website to learn about special exhibitions and to buy tickets or memberships.

2. The Chicago Symphony Orchestra

Often hailed as one of the best symphony orchestras in the world, the Chicago Symphony performs nearly 100 concerts annually. During the year, they perform downtown at the Symphony Center, but in the summer season they move to the North Shore for the Ravinia Festival.

Why this is a romantic thing to do: There’s nothing more romantic than listening to some of the greatest music ever composed with your boo, but it’s not all Beethoven and Brahms – they often feature live performances of movie scores like Star Wars, The Princess Bride, and Harry Potter. 

Check their calendar for upcoming events and to get your tickets.

3. The Magnificent Mile

The most famous stretch of road in Chicago, the Magnificent Mile is 13 blocks on North Michigan Avenue, filled with world-class shopping, dining, museums, and entertainment venues.

Why this is a romantic thing to do: Even if you’re just out for a walk, you and your squeeze will be treated to the city’s most stunning historic architecture. Even if you live in Chicago, the Mile is home to a cadre of luxury hotels, perfect for a romantic staycation.

4. CloudBar at 360 CHICAGO

If Chicago at street level isn’t romantic enough for you, try elevating your expectations with a visit to the new CloudBar at 360 CHICAGO Observation Deck. This is the coolest new bar in town, with views from 1,000 feet up. Enjoy a cocktail, a cold drink and small plates that are inspired by Chicago's vibrant neighborhood flavors. 

Why this is a romantic thing to do: Panoramic sunset and evening views, and one great cocktail will be the date that you and you partner remember for a lifetime. Stay a while, walk around the deck, or for that more adventurous couple, try out TILT - The highest thrill ride in the world! 

Access the Cloudbar with a 360 CHICAGO general admission ticket here. 

5. The Lincoln Park Zoo

Home to more than 200 species of animals, the Lincoln Park Zoo is one of the last free admission zoos in the country. Built in 1868, it’s also one of the oldest. Beyond the amazing exhibits, the summer months are filled with special events like picnics, block parties, and wine tastings.

Why this is a romantic thing to do: Escape the hustle and bustle of everyday life and connect with your significant other while exploring the wildlife and share your love for animals.

Check out the site to see what’s happening for you and your loved one to enjoy together.

6. The Navy Pier

It wouldn’t be a romantic day in Chicago without a walk out on the famous Navy Pier. Boasting some of the best views of the Chicago Skyline.

Why this is a romantic thing to do: Some outdoor couples fun. There are always fun things to do at the Pier like free concerts, dinner cruises on Lake Michigan, or an evening at the Chicago Shakespeare Theatre. And you and your boo definitely don’t want to miss the fireworks all summer long! 

Check out their calendar to see what’s happening.

7. Chicago Food Tours

One thing is for sure – Chicagoans know how to eat well. The best way to experience a local’s knowledge of the city’s best cuisine is to sign up you and your partner up for a food tour. There are a bunch to choose from, including a great food tour of the trendy West Loop restaurant row and any number of great Chicago pizza tours.

Why this is a romantic thing to do: You and your ride-or-die can experience an amazing introduction to Chicago's incredible cuisine and explore the city from a culinary perspective.

8. ChiTown Drive-In

Movie lovers! Featuring modern classics like The Breakfast Club, Spider-Man: No Way Home, and Nightmare on Elm Street, a drive-in movie is a great way to spend a romantic evening together with your significant other. It's a fun, affordable way to enjoy a movie, and it can be a lot more intimate than going to a traditional movie theater.

Why this is a romantic thing to do: there’s nothing more romantic than parking with your significant other and taking in a great movie. And if you’ve already seen it, it’s a good excuse to steam up the windows a little – in a PG kinda way, of course. 

Check their site for showtimes!

9. Morton Arboretum

Take a walk with your sweetheart through this stunning nature preserve in suburban Lisle where you’ll encounter more than 4,000 cataloged species of plantlife. Until March 2023, wander among the towering sculptures of the popular outdoor Human + Nature art exhibition.

Why this is a romantic thing to do: The Arboretum also hosts romantic events like special dinners, Aerial Tree Yoga, and more.

Reserve your tickets here for timed admission or special exhibits and events.

Photo Credit: Alanscottwalker

10. Maggie Daley Park Skating Ribbon

In the winter months, the gradually sloping quarter-mile Ribbon is home to the city’s coolest ice skating rink, complete with skate rentals. In the summer, strap on your rollerblades and enjoy the nice weather.

Why this is a romantic thing to do: Alone time, holding hands, and a fun atmosphere to take in the skyline as you go around the winding path.

If you want to hit the ice this winter, you’ll have to make reservations ahead of time.

11. Promontory Point

This man-made lakeside peninsula in Hyde Park’s Burnham Park is a lovely spot to take a scenic walk with your sweetie. If things are serious between you two, the stunning skyline is a perfect backdrop to pop the question!

Why this is a romantic thing to do: this gem features an intimate view of the city's skyline with seating to relax and enjoy the lakefront.

Photo Credit: Michael Christensen

12. Garden of the Phoenix in Jackson Park

This Japanese walking garden in Jackson Park’s Wooded Island is a beautiful place to take a stroll with the one you love, especially in the spring when the cherry blossoms are blooming.

Why this is a romantic thing to do: Surprising that special flower lover with a wander through heaven. The flowers are at their peak in late April and May, and you can check on their bloom status here. The Japanese even have a name for the act of enjoying the flowers: hanami.

trendy restaurant with dim lighting

13. A Romantic Dinner In The City

A list of romantic things to do in Chicago wouldn't be complete without first mentioning all the intimate dining options this great city has to offer. From cozy bistros to elegant fine dining establishments, Chicago has a vibrant culinary scene with excellent restaurants for couples interested in a romantic dining experience. No matter what your taste, you're sure to find something to your liking in Chicago.

Why this is a romantic thing to do: an intimate dinner in a beautiful setting is a classic date night idea that you can always fall back on. Plus, with Chicago's incredibly diverse cuisines and world-class restaurants, you're sure to find something you'll both love.

14. The Garfield Park Conservatory

Great for a romantic day together all year round, this 4.5 acre botanical garden is often referred to as “landscape art under glass.” Home to thousands of plant species from all over the world, showcased in eight unique display gardens, the conservancy also features regular special events like art classes, guided walks, and concerts. Reservations are free and required for entry.  

Don’t wait, lovebirds! Now’s the time to get out into the city and kindle that flame between you. If you’re looking for more romantic things to do in Chicago, have a look at how we recommend you spend a day on the Magnificent Mile. If the summertime weather is calling your names, check out our comprehensive Guide to Chicago Summer Events. But whatever you do, make sure you do it with the one you love!

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