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Where to Get Engaged in Chicago

Posted on February 13, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

A couple embraces at Millennium Park

A couple embraces at Millennium Park. (Courtesy of Amy Boyle)

City Cast

ShotSpotter’s Future, Ballot Measures Explained, and Most Romantic Spots

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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

Silhouettes of a couple kissing by a Cubs sign

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.
A statue at the Garfield Park Conservatory

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
View from the 360 Chicago Observation Deck at the John Hancock

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
A couple smooches near Art on the Mart.

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
A person kneels in front of their partner at the Millennium Park ice skating rink

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
View from Cindy's Rooftop in the Loop

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.

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