Make Your “Yes!” Moment Unforgettable in the Heart of the City

Proposing to the love of your life? You want it to be iconic. And there’s no better place to pop the question than the Chicago Riverwalk—a stunning, romantic backdrop that shows off the very best of the city. Whether it’s during sunrise, golden hour, or under the shimmering lights at night, this spot delivers every. single. time.


Getting to the Chicago Riverwalk

Let’s be real: Chicago traffic is no joke, and you don’t want to be sprinting in dress shoes or heels. Here's how to get there with minimal stress:

  • CTA (Highly Recommended): Hop on the train and skip the parking drama. The Clark/Lake (Blue/Green/Orange/Pink/Brown Lines) or State/Lake (Red Line) stations drop you within walking distance.
  • Driving? Use SpotHero: Book a parking spot in advance. Seriously—don’t gamble on street parking. Aim to arrive 30–40 minutes early to buffer against delays.
  • Pack Light: There are limited public restrooms and basically zero storage, so leave the extra stuff at home.
  • Accessibility Note: While some parts of the Riverwalk are wheelchair-friendly, there are stairs in many areas. Plan accordingly!



Best Proposal Spots on the Riverwalk

With 1.25 miles of stunning waterfront, you’ve got options. Here are my top picks based on vibe, privacy, and photo potential:

  • The Confluence (Lake Street): Quiet and tucked away, where all three branches of the river meet. Intimate, low-key, and totally romantic.
  • The Arcade (Franklin to State): You’ll get iconic architecture like Marina Towers reflected on the water. Modern, urban, and unmistakably Chicago.
  • The Civic (State to Michigan): A fan favorite. Wrigley Building? Check. Trump Tower? Check. Ultimate city skyline vibes.
  • The Esplanade (Michigan to Lakefront): Open, airy, and full of golden light. Think serene river scenes with big city energy.
  • Under the DuSable Bridge (Michigan Ave): Old-world charm meets dramatic skyline views. A killer combo for timeless photos.



Tips for a Flawless Proposal

Want your big moment to go off without a hitch? Here’s the playbook:

  • Time It Right:
  • Morning: Soft light, quiet atmosphere, fewer photobombers.
  • Evening: Glowing city lights, super romantic, a little more buzz in the air.
  • Hire a Photographer (Hint: Me!): I’ll discreetly capture every moment so you can stay present—and look amazing doing it.
  • Plan a Stroll After: The Riverwalk is made for hand-in-hand, just-engaged walks with dreamy photo ops at every turn.
  • Keep It Chill: Don’t overthink it. This spot is naturally gorgeous. Even if you're nervous (which is normal), it’ll be perfect.



Bonus Photo Locations Nearby

Once the “Yes!” is locked in, take advantage of being in one of the most photogenic parts of Chicago:

  • Goddess and The Baker: Grab a latte and snap some cozy, candid pics.
  • The Wrigley Building: Glamorous, historic, and absolutely iconic.
  • The Chicago Theatre: That glowing marquee? Chef’s kiss for engagement photos.
  • Millennium Park & Cloud Gate (The Bean): Classic Chicago. Enough said.
  • Michigan Avenue Bridge: Killer river views and skyscrapers galore.



Final Thoughts

A proposal on the Chicago Riverwalk? Unforgettable. With the river glistening beside you and the city rising behind you, it’s got all the makings of a legendary love story. Whether you’re planning something big or keeping it sweet and simple, this spot sets the stage perfectly.

Want me there to capture the moment? I got you. Let’s make it magical—without missing a single second.

📍 Open to the Public | Hours: 6 AM – 11 PM

Chicago Riverwalk

FAQ : Proposing at the Chicago Riverwalk

When is the best time of day to propose at the Chicago Riverwalk?

Golden hour (right before sunset) is super popular for that soft, glowing light. But if you want privacy, early morning is clutch—calm, quiet, and fewer people around. Nighttime proposals can also be magical with all the city lights.

Do I need a permit to propose at the Riverwalk?

Nope! The Chicago Riverwalk is open to the public and doesn’t require a permit for personal proposals or photography. But if you’re bringing props or doing anything elaborate, you might want to double-check with the city.

How crowded does it get?

It depends on the time and weather. Weekends and evenings can get pretty packed—especially in summer. For more privacy, go early in the day or on a weekday.

Is the Riverwalk open year-round?

Yes! The Riverwalk is open daily from 6 AM to 11 PM, even in winter. Just be prepared—cold months can get icy, and some areas may be closed for snow or maintenance.

What happens if it rains on the day I plan to propose?

Chicago weather is wild, so always have a Plan B—like under the DuSable Bridge or rescheduling with your photographer. A little drizzle can be romantic, though, if you're up for it!

Can I hire a professional photographer for my proposal?

Absolutely—and you should! A pro (👋 hi, that’s me!) can capture the big moment discreetly and help guide you to the best lighting and locations.

What should I wear for a Riverwalk proposal?

Dress up a little—it’s a big moment! Choose something comfortable but elevated (and photo-friendly!). Also, wear shoes you can walk in, especially if you're exploring after.

Is the Chicago Riverwalk wheelchair accessible?

Some sections are, yes—but many parts include stairs. If accessibility is a priority, scope out your exact location ahead of time or message a local photographer for help choosing the right spot.

Can I bring props like flowers or signs?

Small props? Yes. Just keep it low-key and portable—there’s no storage and security may step in if it looks like a commercial setup. Less is more here!

What are good places to celebrate afterward nearby?

So many! Try Goddess and the Baker for coffee, RPM Italian for a romantic dinner, or LondonHouse rooftop for celebratory cocktails with a view.

A sightseeing boat passes under a red bridge on the Chicago River with Marina City towers in the background.
A couple stands in winter on a snowy riverwalk beneath a red iron bridge in downtown Chicago.
A snow-covered riverwalk in Chicago with people viewing the skyline and iconic red bridge on a winter day.
Winter scene on Chicago Riverwalk with snow covered walkway and red bridge crossing river with skyscrapers in background.
A couple in winter coats and beanies embrace while standing on an icy walkway with urban architecture in the background.
Two people stand on a snowy riverwalk with Chicago's skyline and a red bridge in the background on a winter day.
A person in a warm coat and beanie hat plays in the snow on urban steps during winter while being photographed.
Two people shovel snow off outdoor concrete steps on a winter day.
Couple in warm winter coats holding hands and smiling while walking together outdoors on a city street.
Two people stand on a snowy pedestrian bridge in Chicago with the iconic red bridge and skyscrapers in the background.
Two people stand on a snowy walkway near Lake Street Bridge in downtown Chicago during winter.
Two people share a moment on a snowy wooden walkway with a red bridge and Chicago skyline in the background.
Two people stand on a snow-covered walkway beneath a red bridge with Chicago skyscrapers in the background.
Two people embrace near a snowy riverwalk with Chicago's skyline and a red bridge in the background.
A person proposes on a snow-covered bridge deck with Chicago's downtown skyscrapers rising in the background.