With love in the air and Valentine’s Day around the corner, some Chicagoans might be getting ready to pop the big question. Lincoln Park photographer Amy Boyle identified some of the best spots in the city for every type of proposal.
Most Low-Effort
- An L Ride to or from your favorite station ( or for maximum effort, charter your own train for $3,000)
- Millennium Park
- Lakefront picnic

A more creative spot for Cubs fans to get engaged! (Courtesy of Amy Boyle)
Best Public Display
- While jumbotrons are overrated, outdoor space around the ballparks are more unique.

The Garfield Park Conservatory is perfect for engagements, wedding photos, and more! (Courtesy of Amy Boyle)
Best Private Spot
- Caldwell Lily Pond in Lincoln Park
- Garfield Park Conservatory
- Rose Garden at Grant Park

There’s a reason tourists flock to this observation deck on the Near North Side. (Courtesy of Amy Boyle)
Best Views
- 360 Chicago Observation Deck at the John Hancock
- 31st Street Beach
- Montrose Beach

Appreciate art and architecture? Art on the Mart might be the perfect spot for the big Q. (Courtesy of Amy Boyle)
Most Chicago
- Art on the Mart along the Riverwalk
- Jackson Park Lagoon or Japanese Garden
- The Art Institute of Chicago
- Beneath the Tiffany Dome at the Chicago Cultural Center

Getting proposed in the middle of an ice skating date screams sappy rom-com 😍 (Courtesy of Amy Boyle)
Most Unexpected
- Ice skating at Millenium Park
- Original Potbelly’s on Lincoln Avenue

The city does look especially romantic from this restaurant in the Loop. (Courtesy of Amy Boyle)
Best Restaurant
- Cindy’s Rooftop, but Chicago is world-class for restaurants, and there IS a romantic restaurant for everyone’s taste and budget.



