When Friendship Turns Into Love in the Heart of Chicago
Sometimes, the best love stories begin unexpectedly through the connections we least expect. Shane and Taylor’s story is a perfect example. Introduced by their mutual best friend Ryan Walker-who shares a deep bond with both of them-Shane and Taylor quickly found a connection that blossomed into love. Ryan and Taylor grew up together, and Shane and Ryan became fraternity brothers in college. One visit from Taylor to Ryan’s place led to that fateful introduction, and the rest, as they say, is history.
As a destination Chicago wedding photographer, capturing Shane and Taylor’s engagement session in downtown Chicago was a true pleasure. Their love story, set against the iconic cityscape, reflects the vibrant energy and timeless romance that Chicago offers couples from near and far.
Why Choose Downtown Chicago for Your Engagement Session?
Chicago’s downtown is a dynamic blend of historic architecture, modern skyscrapers, and urban charm. It’s a playground for photographers and couples alike, offering a variety of stunning backdrops that tell your unique story.
Iconic Engagement Locations in Downtown Chicago
- Chicago Board of Trade
141 W Jackson Blvd, Chicago, IL 60604
With its dramatic beaux-arts columns and iconic clock façade, this historic building provides a timeless, elegant backdrop perfect for editorial engagement photos. - Chicago Theatre
175 N State St, Chicago, IL 60601
The famous marquee and vibrant urban energy make this a must-visit for couples wanting bold, memorable images. - Michigan Avenue & The Magnificent Mile
Michigan Ave, Chicago, IL 60604
Capture the heartbeat of Chicago with shots along this bustling avenue, featuring stunning architecture and city life. - Navy Pier
600 E Grand Ave, Chicago, IL 60611
From the iconic Ferris Wheel to the Crystal Gardens, Navy Pier offers whimsical and romantic spots for engagement photos. - Chicago Riverwalk
Chicago Riverwalk, Chicago, IL 60601
Murals, unique shops, and river views create endless opportunities for candid and editorial portraits. - Wrigley Building
400 Michigan Ave, Chicago, IL 60611
A favorite for its striking facade and river views, perfect for classic and sophisticated engagement photos.





The Session: Urban Romance and Authentic Connection
Shane and Taylor’s session was a beautiful mix of candid moments and editorial portraits. We explored the vibrant streets and iconic landmarks of downtown Chicago, capturing their chemistry against the city’s stunning backdrops. Their laughter, affection, and ease in front of the camera made every shot feel natural and heartfelt.
Indoor Engagement Session Options for Chicago Couples
Chicago’s weather can be unpredictable, but the city offers incredible indoor locations to complement your engagement session:
Salvage One
1840 W Hubbard St, Chicago, IL 60622
Vintage décor and eclectic spaces for unique, creative portraits.
Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603
Elegant indoor gardens and classic architecture provide timeless settings.
Chicago Cultural Center
78 E Washington St, Chicago, IL 60602
Home to the stunning Tiffany dome, perfect for dramatic, indoor portraits.
Garfield Park Conservatory
300 N Central Park Ave, Chicago, IL 60624
A tropical oasis with year-round greenery and natural light.
Lincoln Park Conservatory
2391 N Stockton Dr, Chicago, IL 60614
Lush themed plantings and beautiful glasshouses.







Planning Your Chicago Engagement Session: Tips for Success
- Timing: Early mornings and golden hour evenings offer the best light and fewer crowds.
- Wardrobe: Dress stylishly but comfortably; layers work well for changing weather.
- Permits: Some locations require photography permits-plan ahead to secure them.
- Personal Touches: Bring props or meaningful items to make your session unique.
- Trust Your Photographer: I’ll guide you through poses and locations to make your session fun and stress-free.
Why Choose Me as Your Chicago Engagement Photographer?
As a Chicago photographer, I combine editorial style with documentary storytelling to create timeless images that capture your authentic love story. My deep knowledge of Chicago’s best locations and seasons ensures your engagement session is not only beautiful but also seamless and memorable.



Recommended Chicago Wedding Vendors
Planners:
Florists:
Frequently Asked Questions
Q: Can we combine multiple locations in one session?
A: Yes! Many couples love mixing iconic outdoor spots with cozy indoor venues.
Q: How do you handle weather changes?
A: I always have backup locations and flexible scheduling to ensure beautiful photos regardless of weather.
Q: Do you offer both photography and videography?
A: Yes! I provide both services to capture your story fully.
Ready to Book Your Downtown Chicago Engagement Session?
If you’re searching for a destination Chicago wedding photographer, Chicago engagement photographer, or Chicago photographer who will tell your love story with artistry and heart, contact Stills by Hernan | Stills the Studio today.
Let’s create timeless images that celebrate your unique journey together in the heart of Chicago.
These are great pictures! They capture the love with all the smiles 🙂