A Picture-Perfect Proposal at the Chicago Riverwalk


Proposing to the love of your life is a moment you’ll never forget, and the Chicago Riverwalk provides one of the most breathtaking and romantic settings for a proposal in the city. Whether it’s sunrise, golden hour, or under the city lights at night, this location never disappoints.


Getting to the Chicago Riverwalk

One of the biggest challenges with planning a proposal at the Riverwalk is getting there. Here are my best tips for making the journey smooth:

  • Public Transit: Taking the CTA is the easiest way to arrive stress-free. The closest L stops are Clark/Lake (Blue/Green/Orange/Pink/Brown) or State/Lake (Red Line).
  • Parking: If you’re driving, use SpotHero to reserve a parking spot ahead of time. Traffic can be unpredictable, so I always recommend arriving 30-40 minutes before your proposal time.
  • Travel Light: The Riverwalk has limited public restrooms and no convenient storage areas, so carrying minimal gear is key.
  • Accessibility: There are many stairs along the Riverwalk, making some areas less wheelchair-friendly.


Finding the Perfect Proposal Spot

With 1.25 miles of stunning waterfront views, the hardest part about proposing here is picking the perfect location! Here are my top recommendations:

  1. The Confluence (Lake Street area) – This section offers views of where the three branches of the Chicago River meet. A more private spot for an intimate proposal.
  2. The Arcade (Franklin to State Street) – This stretch features some of the most famous architecture, including reflections from the Marina Towers.
  3. The Civic (State Street to Michigan Avenue) – One of the most popular proposal spots! You’ll have the iconic Wrigley Building and Trump Tower in the background.
  4. The Esplanade (Michigan Avenue to Lakefront) – The most scenic and open part of the Riverwalk, with gorgeous water reflections and cityscape views.
  5. Under the DuSable Bridge (Michigan Ave Bridge) – A stunning spot with old-world charm, offering dramatic bridge and skyline views.


Proposal Tips for a Flawless Moment

  • Pick the Right Time: Early mornings have soft, glowing light and fewer crowds, while evenings have a romantic, twinkling cityscape.
  • Consider Hiring a Photographer: As a Chicago proposal photographer, I can capture your moment in a discreet and authentic way.
  • Plan a Walk Afterward: The Riverwalk offers endless opportunities for romantic post-proposal photos.
  • Don’t Overthink It! The Riverwalk is such a naturally beautiful setting that your proposal will look amazing no matter what.


Nearby Photo Locations

After you pop the question, you’ll want to celebrate with some stunning photos. Here are the best nearby spots for engagement pictures:

  • Goddess and The Baker – Stop by this adorable café for candid coffee shop photos.
  • The Wrigley Building – One of the most iconic backdrops in Chicago!
  • The Chicago Theatre – A short walk away, this landmark provides an unforgettable engagement photo.
  • Millennium Park & Cloud Gate (The Bean) – Only a few blocks away for another classic Chicago look.
  • Michigan Avenue Bridge – For epic river and skyline shots.


Final Thoughts

A proposal at the Chicago Riverwalk is always magical. No matter the time of day or season, the backdrop of the Chicago skyline and river reflections creates an unforgettable scene. If you’re planning to propose and want a professional to capture it perfectly and discreetly, let’s connect! I’d love to help you plan and document your special moment.

📍 Free to the public | Hours: 6 AM - 11 PM

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.