Where to Propose in Chicago in 2025: 12 Best Spots for an Unforgettable “Yes”
If you’ve been looking for the best spot where to ask the largest question of your existence, then here are the top 12 picks that we recommend during your visit to Chicago in 2025. Each spot has valuable tips we’ve acquired guiding couples to plan their dream proposal here.
Millennium Park (Cloud Gate & South Garden)
No proposal list for Chicago is complete without Millennium Park. Most couples head straight to Cloud Gate — “The Bean” — for that classic reflection shot. If that’s your vision, aim for early morning on a weekday before the crowds roll in.
Just steps away, though, is the South Garden — a peaceful, shaded escape that’s often overlooked. It’s one of our favorite hidden spots for couples who want a more intimate, greenery-filled backdrop without losing the city vibe.
Whether you choose the buzz of The Bean or the calm of the garden, we always suggest including a professional photography package. A discreet photographer captures every raw, emotional second — the moment you drop to one knee, the smile, the surprise, the yes. Then, we can grab a few portraits after with Chicago’s skyline glowing around you.
LondonHouse Chicago Rooftop & Cupola
If skyline drama is what you’re after, few places rival the rooftop of LondonHouse. The Cupola — perched high above the Chicago River — is a true hidden gem, offering panoramic views of the skyline in every direction. Proposals here always feel cinematic, especially as the city lights begin to glow at sunset.
For couples wanting to go all-in on the moment, this space pairs beautifully with a romantic setup: “Marry Me” marquee letters, scattered rose petals, and soft candlelight create just the right mix of grandeur and intimacy. The architecture does the rest. It’s one of those rare spots where everything — the view, the lighting, the energy — works in your favor.
Ambassador Hotel Rooftop
If historic charm is your style combined with some privacy, the best spot is the Ambassador Hotel’s roof. While some other terraces are more lively, this is a quiet, timeless spot that is perfect if you want something classy yet doesn’t need to be flashy. We can also provide a beautiful Flower Arch to complete the setup.
Here’s the tip – this rooftop is popular so pricey if you need something more affordable and less mainstream we can you covered!
North Avenue Beach
For that iconic Chicago skyline paired with the sound of waves, North Avenue Beach is as romantic as it gets. It’s especially stunning at golden hour, when the city lights begin to glow and Lake Michigan becomes your backdrop.
Depending on your vision, we can tailor the experience:
Some couples opt for a cozy picnic setup — complete with a blanket, champagne, and fresh roses nestled in the sand. Others go bigger with a full Flower Arch Installation, like a heart-shaped design framed by soft candlelight and florals leading down to the water.
Whether you lean casual or elegant, this setting can be shaped into a moment that feels just right for the two of you.
Chicago Riverwalk (near Wrigley Building & bridges)
The Riverwalk is perhaps the most photogenic proposal spot in Chicago, notably around the Wrigley Building and DuSable Bridge. Water mirrors the city lights, bridges curve overhead — it’s movie-esque.
Pro tip: do it at dusk, when the city’s alight but the sky still has hue. We typically stand photographers on the other side of the river so the skyline is behind the couple. It’s the kind of place that’s like something out of a movie. Add a photographer or our Romantic Flower and Candle Heart setup to make the moment even more magical.
Lincoln Park Honeycomb Pavilion & Nature Boardwalk
If your taste is the skyline minus the crowds around Millennium Park, the Lincoln Park Honeycomb Pavilion is the ultimate compromise. The wooden construction organizes the city skyline behind you automatically, and the Nature Boardwalk incorporates foliage, lakes, and wildlife.
This location is stellar during the spring and autumn seasons, where the colors are the best they come alive, as the crowds are smaller. If your photography style is artistic, then this place is among the most diverse backdrops in the country.
It’s also a beautiful place to capture your proposal on video — our professional videographer can discreetly record the moment and create a cinematic keepsake that captures both your emotions and the incredible scenery.
Alfred Caldwell Lily Pool
Hid away in Lincoln Park, this is the ultimate hidden gem. Stepping into the Lily Pool is like entering a secret garden — serpentine stone paths, little bridges, summer water lilies.
It’s also among the most private outdoor locations in the city to propose. We do recommend checking the hours, as the gates do close at sunset. Propose just before closing time for the most quiet time possible.
To make it even more special, you can surprise your partner with a cozy picnic setup featuring champagne and elegant décor, creating a romantic moment that feels effortless and deeply personal.
Promontory Point (Hyde Park)
If lakefront romance with smaller crowds is your goal, skip the crowds south to Promontory Point, Hyde Park. It offers expansive open vistas of the skyline over the lake, as well as a serene park environment.
It’s especially lovely at sunset, where the sun drops behind the city. It’s also a wonderful option if you’d like to arrange candles, lanterns, or even a little picnic. It’s open space that lends itself to some wonderful makeshift arrangement without disruption.
Milton Lee Olive Park
It’s also one of our personal proposal favorites because it combines rare privacy with a jaw-dropping view of the Chicago skyline. The park juts out into the lake, creating a quiet, secluded corner with completely unobstructed city views.
The best time to be there is early morning — just after sunrise — when the lake is calm, the light is soft, and the city begins to glow behind you. It’s peaceful, romantic, and feels like your own secret slice of Chicago.
For couples who want to make the moment feel even more intentional, this location pairs beautifully with a Romantic Flower Arch setup, complete with soft candlelight and rose petals. The structure frames the skyline perfectly while keeping the focus on the two of you — an elegant touch that transforms a quiet park into something unforgettable.
Garfield Park Conservatory
Winters in Chicago can be unforgiving, yet Garfield Park Conservatory is the ultimate year-round escape. It’s a tropical-paradise-feeling place, complete with plants, waterfalls, and foliage galore.
It’s among the best proposal spots inside, come cold winter. Even the humidity is a plus, as it provides a natural glow effect. We would recommend posing around the Fern Room or the Palm House, where the most complimenting backdrops are. Our professional photographer can also capture your proposal among the ferns or under the towering palms
The Rookery Building Light Court
It’s a dream venue for architectural- and history-loving couples. Frank Lloyd Wright designed the Light Court, where there are flying glass ceilings and the most exquisite details that any proposal will be majestic-looking.
Since it’s also a weather-proof spot, being inside, it’s also a safe-bet option. However, do keep this in mind that sometimes permission would need to be arranged ahead of time — something we always do for our clients. It might be challenging to set up a decor so we recommend to opt for professional photographer or videographer to capture the moment!
Chicago Cultural Center
Not many know just how stunning the Chicago Cultural Center is. It’s richly decorated mosaics and the globe’s largest Tiffany glass dome make it feel as if entering an actual European palace.
It’s an ideal pick for a nontraditional indoor proposal. It’s particularly attention-grabbing if your partner’s an art, history, or architecture buff. Propose beneath the dome, then head outside for photos with Millennium Park, just next door.
All Set to Plan Your Proposal?
If any of these Chicago locations suits your dream, we can assist you in making it a reality. From obtaining permits to arranging flowers to concealing a photographer just where they cannot be seen, our role is to enable all that is important for you to think about your love of your life and those four enchanting words.
Want a unique proposal moment? Merge picnic, rooftop, fountain, or limo, and reach out to Paparazzi Proposals to make your special moment magical for you.
