City Cast Chicago logo

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

00:00:00

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.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

The latest in Chicago

Chicago, ExplainedAugust 21

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.

A man in a cubs uniform bracing for a man in a white sox stealing a base
Keep It LocalAugust 20

How Transit Tees Turns Chicago’s Quirks Into Board Games

From board games about the city’s history to puzzles of iconic maps to card decks featuring local wildlife, Transit Tees’ teams of creato...

A person writing on a gridded paper that says "Chicago 1893" There's also a board game with an assortment of different houses for the board game on it. There is also A bowl of popcorn and a soda on the table
Keep It LocalAugust 20

Your Guide to Chicago’s Toy Stores

From vintage toys to a workshop series for aspiring toy inventors, Here's a list of places that’ll help you spoil the kids in your life a...

A table with an assortment of different stuffed animals
Keep It LocalAugust 13

Your Guide to Chicago’s Stationery Stores

Whether you’re actually going back to school soon or you just love analog hobbies, these local shops will help you find all kinds of stat...

A large group of people inside a store. They are looking at an assortment of items
Food & DrinkAugust 13

5 New Spots to Dine and Drink

Chicago is hot AF right now — and so is the dining scene. These recent openings have caught our eye.

A room with velvet drapes on every wall. On the ceiling there are chandeliers and people are sitting at a booth
Keep It LocalAugust 13

Family-Run Atlas Stationers Has Supplied Chicago’s Pens For Decades

For decades, the family-run shop delivered office supplies in bulk to offices in the Loop.

The outside of a brick building, the sign says "Atlas Stationers Inc"
Keep It LocalAugust 6

Your Guide to Dog-Friendly Patios

Want to enjoy patio weather, but hate leaving your pup at home? Check out our guide on the best dog-friendly patios in Chicago.

A curly-haired golden doodle wearing a harness steps into a small blue kiddie pool filled with colorful beach balls at a dog-friendly outdoor patio, with diners seated under blue and white striped umbrellas in the background.
Keep It LocalJuly 30

Why Creatives Love Epiphany Center for the Arts

Five years ago, a group of artists transformed a shuttered, historic church at 201 S. Ashland Ave. into Epiphany Center for the Arts. Sin...

An indoor space with hanging lights and a wood floor. The walls are short but the roof is very tall. There are small remnants of a church left like the windows