When I planned a romantic escape in the Windy City, I was surprised by just how easy it was to find those unforgettable moments. These attractions in Chicago gave us everything from jaw-dropping skyline views to quiet strolls by the lake—and plenty of cozy spots in between. Whether we were watching the sunset or sharing a candlelit dinner, the city made it all feel extra special.
Highlights:
- Watch the sunset from the Skydeck or 360 Chicago – The views made us feel like we were on top of the world.
- Stroll hand-in-hand along the Riverwalk or Lakefront Trail – Perfect for soaking in the city without the rush.
- Dine at intimate restaurants with skyline views – We found the kind of spots where the atmosphere is as good as the food.
- Take a romantic architecture boat cruise – Floating past historic buildings while the sun set was pure magic.
- Explore the Art Institute or Garfield Park Conservatory – Whether it was art or nature, these peaceful escapes gave us plenty to talk about.
Unique Romantic Activities and Attractions in Chicago:
Breathe in Botanical Beauty at Garfield Park Conservatory - Wander through lush glasshouses and vibrant gardens in one of the country’s largest conservatories
Shop, Dine, and Stroll the Magnificent Mile - Luxury brands, skyline views, and Chicago’s premier stretch of retail energy
See the City Differently with Chicago Architecture Foundation Tours - Hop on a river cruise or walking tour to uncover the stories behind the skyline
Soar Above the City at 360 Chicago - Dare to “Tilt” and take in panoramic lake and city views from 94 floors up
Experience Local Flavor in Andersonville - Historic Swedish roots, indie shops, and LGBTQ+ pride meet in this welcoming neighborhood
Step Out on The Ledge at The Skydeck - Glass boxes and heart-racing views from the top of Willis Tower—103 stories high
Taste the World at the Chicago French Market - From crepes to ramen, this gourmet food hall is a sensory journey you can snack through
Dive Into Discovery at Shedd Aquarium - Meet belugas, jellyfish, and reef sharks in one of the world’s leading aquariums
In Summary...
(and if you want to revisit my photo journey)- • Breathe in Botanical Beauty at Garfield Park Conservatory
- • Shop, Dine, and Stroll the Magnificent Mile
- • See the City Differently with Chicago Architecture Foundation Tours
- • Soar Above the City at 360 Chicago
- • Experience Local Flavor in Andersonville
- • Step Out on The Ledge at The Skydeck
- • Taste the World at the Chicago French Market
- • Dive Into Discovery at Shedd Aquarium