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August 16-18, 2024: Passionate Street & Urban Weekend Mentorship Workshop CHICAGO Edition with Steve Simon

Join Steve Simon for an Intensive & Transformational Shooting Experience one of the world's most photogenic cities, Chicago.

  • Dates:Aug 16-18, 2024
  • Genre: Street & Urban Photography
  • Group Size: Max 6 participants
  • Skill Levels: All
  • Includes: Critiques & Lectures, Welcome Dinner, Architectural Cruise, local transportation, teaching materials, snacks

This is a mentorship workshop where Steve meets with each participant prior to the start for a one-on-one Zoom meeting assessment of your portfolio and a tech check to discuss gear and best ways to use it regardless of your system brand. There is a pre-workshop group meeting & lecture as well as a post workshop Zoom class and post one-on-one Zoom meeting as part of the mentorship. Steve will be teaching you new and powerful street photography techniques guaranteed to push you from your comfort zone to new heights in your work and share his street-shooting philosophies gleaned from a lifetime of wandering urban places with his camera.

See All Steve Simon Passionate Photographer Workshops Here

Workshop Details 

Join award-winning street photographer Steve Simon for an unforgettable weekend of living and breathing photography in one of the world’s most visual cities, CHICAGO.

This is a mentorship workshop where Steve meets with each participant prior to the start for a one-on-one Zoom meeting assessment of your portfolio and a tech check to discuss gear and best ways to use it regardless of your system brand. We make tweaks to enhance your speed of response which might include back button autofocus, Auto ISO, Easy Exposure Compensation, frame rate and playback options along with other best practices all designed to simplify your process and build your muscle memory so the technical fades to the background and you increase you success rate. 

This will be an intimate 3-day weekend masterclass (limited to just 6 students) is designed to maximize both the learning experience and your ability to create a unique and powerful portfolio of imagery from Chicago. 

The pre-workshop personal zoom session and portfolio review insures each student is ready to maximize the shooting part of the workshop when we arrive on location. One more pre-workshop Zoom Group session and lecture and we are ready to maximize our workshop experience.

In Chicago, we begin with a meet, greet and lecture followed by an ice-breaking photo walk in the area close to the hotel. We then share a fabulous meal at one of Chicago's landmark pizza restaurants for authentic Chicago deep-dish and great conversation.

We wake up Saturday Morning with the much heralded Chicago Architectural Cruise to get great shots from this unique floating shooting position. 

    You will explore the vibrant, visually rich places and neighborhoods Chicago is famous for and shoot from great vantage points for capturing Chicago's architecture, urban landscapes, cityscapes and we will visit some hidden gems.

    Steve has scouted locations to work out a final detailed itinerary to balance the street and urban work we pursue. Though the schedule may seem packed, woven into the program is down time to relax, edit your work and percolate on your Chicago experience.

    Post Workshop Mentorship

    Our post-workshop Zoom session means we won't be rushing at the end to choose and process images for Sunday Critique, giving you time to look over your entire take for stronger submissions and a deeper discussion with will make for  a more productive final meetup.   


    We encourage flexibility and independence among participants and will attempt to personalize your experience whenever possible. If you fall in love with an area and want to continue working there–you are encouraged to do so.

    Limiting our workshop to six participants, allows me to tailor this workshop to meet the needs of each participant. Lectures and assignments will be personalized to get you out of your comfort zone and push you forward in your work.

    The city of Chicago is fairly easy to navigate but you will be doing a lot of walking so keep that in mind!

    Our Base:

    Our Base: The Sofitel Chicago - Magnificent Mile

    Our base, the perfectly located Sofitel Chicago : 20 E Chestnut St, Chicago, IL 60611, the ideal place and base for our workshop, a luxurious contrast and respite from the busy streets of Chicago.


    Aside from our base hotel, there are many great hotels and AirBNB options close to our downtown venue. 

    Street Philosophies

    “When I have a camera in my hand, I know no fear.” – Alfred Eisenstaedt

    Steve will be teaching new and powerful street photography techniques as well as best practices for capturing the amazing urban opportunities Chicago offers using your tripod and live view--guaranteed to push you to new heights in your work. Steve will further share his street-shooting philosophies gleaned from a lifetime of wandering urban places with his camera. 

    He will help you find your own unique vision and street style through assignments created to get you past photographic fears and cliches to capturing lyrical, poetic and decisive moments that communicate the energy of the city.

    But mostly you will be shooting the theatre and architecture that is the street; sometimes together, often on your own.

    All levels of photographic experience can benefit from this workshop. Passion is the requirement. 

    You’ll learn about the “rhythm of place” and we will discuss the laws and ethics of street photography as well as dealing with difficult situations that might pop up.

    You will define a strategy for capturing the rich daily life of people on the street; overcoming fears and shyness, approaching strangers, framing, juxtaposition, layering your compositions, letting the image come to you and whether color or black and white best suits your vision.

    And we will have so much fun!

    “I am a tourist.“ – Garry Winogrand


    Street Tech

    We will talk urban-tech with Steve giving you his minimalist view on gear along with simplified shooting processes to maximizing your response time to capture decisive moments.

    Steve’s street tools include Nikon mirrorless and DLSR cameras; along with a carefully curated selection of lenses. He is also familiar with a wide range of equipment to help you maximize your mirrorless, compact, rangefinder, DSLR or even your camera phone for compelling urban images.

    Though our focus is on vision more than gear, we will talk lenses, auto focus, zone focusing, shooting form the hip, using live view, flash, camera support and tripods and a host of other tips, tricks, distractions and ideas that will improve your work dramatically. Steve will go over his post-process workflow in Lightroom. 

    It’s a street and urban photography masterclass but the lessons learned here will benefit you in all genres of image-making.



    In class, we will examine a selection of your best or most interesting work from the previous day.

    These daily critiques are of crucial importance, where we share ideas and constructive criticism looking through each others’ images. Our workshop will be a “safe place” for group discussions with suggestions and new ideas put forward.

    Steve will help guide participants work into a cohesive portfolio of images, through careful culling. You will be encouraged to take on a theme over the week for your final portfolio. 

    “A picture is the expression of an impression. If the beautiful were not in us, how would we ever recognize it? “ – Ernst Haas


    We schedule our lecture/critique sessions to take advantage of the light for shooting. We will grab lunch and eat back at our venue to maximize our time, allowing a rest-break before the afternoon/evening shooting sessions. 

    You will explore some of the following neighborhoods and places in the city. 

    Street Locations

    • The Art Institute (good for a rainy day)
    • Wicker Park
    • Pilsen
    • Little Village
    • Ride the L Speed Shoot
    • Theater district
    • Rush Street
    • Michigan Ave
    • Chinatown

    Architectural/Urban Locations

    • University of Chicago
    • Millennium Park
    • Museum of Contemporary Art
    • Parking garages
    • Water Taxi or Chicago Architecture boat tour
    • 18th St Bridge (near Chinatown)
    • Palmer House
    • The Rookery