Romantic Things to Do in Chicago, IL

Serene gardens filled with diverse plants create a beautiful escape. Its free entry and romantic atmosphere make it a perfect spot for couples.

Second City Works Inc

Open until 6pm

Timelessness defines this iconic venue, where legendary comedians began their journeys, making it a must-visit for laughter and entertainment.

Navy Pier

Open until 12am

3.5

Endless options for fun await at Navy Pier, where I can savor waterfront dining, enjoy iconic rides, and take in stunning views of the city.

Hopemark Health Millennium Park

Open until 5pm

Captivating art installations and scenic city views invite leisurely strolls with my partner, making it a perfect spot for romance.

Tortazo - Willis Tower

Open until 7pm

Stunning views define the Skydeck at Willis Tower, especially from the glass Ledge—a thrilling spot perfect for unforgettable photos.

AIRE Ancient Baths - Chicago

Open until 11pm

Enchanting and tranquil, AIRE features candlelit thermal baths in a stunning restored factory, creating a memorable escape for couples.

Cindys Rooftop

Open until 11:59pm

Breathtakingly positioned, Cindy's Rooftop offers panoramic views of Millennium Park and Lake Michigan, perfect for unforgettable romantic moments.

Penguin Foot Pottery

Open until 9pm

Creative workshops here allow couples to bond while learning pottery skills, making for a memorable hands-on experience in Logan Square.

The Aviary

Opens at 5pm

Exquisite combinations of drinks and dining await at The Aviary, where adventurous couples can savor innovative, interactive cocktails together.

Music Box Theatre

Open until 12am

Charming is the Music Box Theatre, offering a historic ambiance along with indie films, themed events, and a cozy cocktail lounge experience.

Chicago Cultural Center

Open until 5pm

Remarkable features like the shimmering Tiffany Dome and free, dynamic art events make the Chicago Cultural Center a cultural gem worth visiting.

Soundings at Shedd Aquarium

Open until 4:30pm

3.5

Diverse marine life like belugas and stingrays create an immersive experience at Soundings, perfect for sharing joyful moments together.

360 Chicago

Open until 11pm

Elevating views from the 94th floor, the TILT ride offers an unmatched experience of the Chicago skyline while enjoying a drink at CloudBar.

City Winery Chicago

Opens at 4pm

3.5

Whimsical nights await at City Winery Chicago, where I enjoy wine-pairing dinners, live music, and guided tours in an urban winery setting.

Performance Bar, AKA David's Bar. Open Mon - Sat at 5:00 P.M. and Sunday afternoon.

Chicago Magic Lounge

Opens at 5pm

Uncommon performances set the Chicago Magic Lounge apart, where hidden wonders behind a laundromat facade enchant audiences in a speakeasy setting.

Maggie Daley Park

Open until 9pm

Delightful vibes fill Maggie Daley Park, with its unique skating ribbon and countless fun activities like mini-golf and climbing year-round.

Museum of Contemporary Art - Chicago

Open until 5pm

Vibrant exhibits and innovative architecture make this museum a must-visit for experiencing modern art in a dynamic setting.

Lincoln Park Conservatory

Open until 5pm

Refreshing greenery and exotic species like orchids create a peaceful escape, ideal for couples seeking a cozy, low-key date in winter.

Bobby's Bike Hike

Open until 6:30pm