Art & Design

A survey of art, architecture and design in the Windy City.

Photo Challenges

Every one of these challenges is either a clue for, or a description of, photos you can take in Chicago.
Each clue can be interpreted creatively – so dare to conceive your own answer to each challenge. Don't aim to do it won't get finished until September.

Pick a worthy challenge for yourself, and aim to complete it.

Always aim for more than a snapshot. Aim to compose and capture a compelling image.  Look at the previews of the shots you take – look for distractions –  then reshoot to get a more dynamic image.

After we get back home, we’ll post and compare our image sets. We’ll vote on the most impressive image sets.

— and you can thank Aaron Landry for coming up with some of the best of these.

The Top Ten | The Second Twenty | The Third Thirty | The One | Complexities

Architectural Samples | Architectural Documentation

Top 10

These are easy...but not entirely. They are the essentials. If you don't capture these, then you're not observing much (so...why did you come?).

  • Truly Chicago windows
  • Less is more Miesian
  • Beside Picasso
  • My Pritzker performance
  • Tiffany at Macy’s
  • Meet Big John
  • Ant’s Eye View:  From the bottom, look up. Capture the intense, receding perspective of vertical architecture.
  • Petting the Lion
  • Skyline from the Shedd
  • A Bean Skyline: capture the city in a  Cloud Gate reflection — get lotsa buildings & few people in the shot.

The Second Twenty

These are not too bad...but you'll have to be more alert to catch them.

  • The Spire’s footprint 
  • Sullivan’s signoff at CPS
  • Rookery rooks
  • Washington’s Winter Garden
  • The goddess Ceres
  • Chunks’o Fort Sumter, Bunker Hill, the Parthenon & the Moon. (at one address)
  • Mannequins at Work
  • Persian Bull Staredown
  • Inner city corncobs
  • Buffeting duBuffet
  • Big Fish at the Shedd
  • Spiraling in the Contemporary
  • Seasonal Chagall
  • Union Station wait space
  • Swinging the biggest bat
  • Downing a Chicago dog
  • Walking the BP Snake
  • Sunrise across Lake Michigan
  • Dancing* with the Flamingo (* choreographing enthusiastically)
  • Irresistibles:  capture pastry or candy in a display case that is really, really hard to resist.

The Third Thirty

Some of these are a bit tougher still...and some are not.
How many can you get? You'll likely go past most of these. A few involve taking the right tour or turn. Some involve some time to plan and shoot. Pick out a few and try to work them out. Compare notes with others — see if you can work together to fill your photo portfolio.

  • Fort Dearborn relief
  • Street Performers in action.
  • Dynamic Type & Signage
  • The 3000 year old El
  • The house that banished Wright
  • Sunrise or Sunset from Navy Pier.
  • Streetcraft:  A piece of Chicago-native street art. (Graffiti, Wall or Feature Painting), or a temporary public art installation.
  • Peking in Chicago
  • Gargoyles and Creatures:  A gargoyle of any sort.
  • Down on the River, explore what's underneath Chicago’s great bridges.  (?can you capture a raised bridge from the bottom?)
  • Ad Infinitum:  Explore repeating features or elements – tessellations, details, fenestration, colonnades
  • Chicago Ants — aerial view of people.
  • You’re not in Searcy anymore:  Find an interesting place to eat that is nothing like back home. Or, maybe a shot of whatever that bizarre dish that you just ordered.
  • Chicago Politics:  somebody or group campaigning or advocating an issue on the street.


  • Explore dynamic shadows in Chicago’s canyons.
  • Yesterday’s News: Find some old painted building advertisements.
  • Observing the Observer: someone interesting at the Art Institute — secretly capture their fascination.
  • In your eye: the skyline in someone’s sunglasses?
  • Lincoln Park Beasties. 
  • Chicago Fire Survivor
  • Nighttime skyline
  • Riverview from the L
  • A Windy City Apple
  • A Rock of Gibraltar
  • The world’s tallest church. 
  • Gothic Quad 
  • Top of the Navy Ferris
  • Roving the Robie
  • Underground Chicago 
  • Dead Sea Scroll fragment
  • ...and a few sticky spares…

    • Ten hanging stories
    • Modern entry to Tartarus
    • You and You Alone:  get a self-portrait-reflection with you and only you…but as much city as possible.
    • A Rex named Sue
    • If you spot President Obama checking out his old hood, yeah, it's a good idea to snap a shot before the guys in dark glasses grab you.

The One

  1. Mixed Beans:  Get the whole group of us in one Cloud Gate reflection.

  2. (think about it…how would you set  it up?  What part of the Bean would you use?  What time of day might the sun be best?  Propose your best concept…sketch it out…take some trial shots.  Then talk us into trying it your way!)

Five Complexities

These shots, or sets of shots, involve some planning, negotiating or time — they’ll involve collecting imagery while in Chicago, and then editing and assembling at HU.  Conceive a unique concept, then create a way to do it—then do it!

  • Mimic or reinvent an artwork you discovered in the Art Institute.  (any medium)
  • Chicago Panorama.  Plan a tall or a wide panoramic image made of many images arranged as one finished work. This can be a rough photo collage, ala David Hockney, a painting/drawing, or a carefully digitally stitched panorama (using Photoshop or Hugin).
  • Urban Monet:  create a series of images of changing colors and reflections in a single scene.  You might  even explore varied light, shadow and weather conditions through reflections on a single building.
  • At the Speed of Light: create a series of images that capture lights in motion; try shots out of focus or with extended exposures.
  • Composition of Chicago Trip detritus: Collateral, Tickets, Passes, Receipts, Brochures, Maps, Wrappers, Notes, Sketches, Etc...

Architectural Sites and Samples

A few of these are challenges.  Most are architectural sites, details or styles to look for.

  1. A Wright neighborhood
  2. Rusticated arches
  3. Paladian Windows
  4. Stick Style
  5. Queen Anne digs
  6. Gothic Tracery (e.g. Tribune Tower detailing/entrances, etc.)
  7. Gothic Quadrangle
  8. Seville Cathedral’s ascending descendant (the tower on the

Architectural Documentary

Pick one of these architectural themes —  then explore just how many different ways a particular architectural form can be expressed.  

Complete your documentation:
a) Take tight shots for detail, as well as
b) wide shots for context. 
c) Make notes on the address/location of your shots. 

Look hard for as many variations as possible.  Find out what theme your friends are looking for, and help each other find examples.

  • Classical Orders:  Ionic Colonnade ; Doric colonnade; Corinthian colonnade
    (can you capture them all in one photo?) (look for variants, both in columns and in pilasters)
  • Clocks & clock towers
  • Windows, windows, windows
  • Doorways, Gates & Entrances
  • Stairways & Stairwells
  • Skylights and domes
  • Railings & Balustrades
  • Elevators, inside & out
  • Cornices and rooflines
  • Bridges and elevated walkways
  • Survey of Styles:  Richardsonian Romanesque, Gothic, Beaux Arts, Prairie Style, Stick Style, Queen Anne, International Style, Modernism, Post-Modernism…
    (either pick one style and document it well or create a survey of all of these styles. You might give your images some common structure or composition.)


One of two lion's framing the main, Michigan Ave. entrance to the Art Institute. By Edward Kerneys. 1893. (affectionately modified for local loyalties).
Anish Kapoor's Cloud Gate (a.k.a. The Bean) In Millennium Park on Michigan Ave. a block north of the Art Institute.


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