What kind of experience are you looking for?
And which city?
ChangeSpot a Chicago Marina City corncob
Find Marina City's twin corncob towers from the river or city. Photograph the round towers.
Spot a Chicago Navy Pier Ferris wheel
Find Navy Pier with its Centennial Wheel. Photograph the wheel.
Spot a Chicago Polish or German bakery
Find a Polish (paczki) or German (pretzel) bakery in Chicago (Avondale, Lincoln Square). Photograph the storefront.
Spot a Chicago skyline view
Find a view of the Chicago skyline from the river, Lake Michigan or a viewpoint. Photograph the silhouette.
Spot a Cubs or White Sox kit
Find a Cubs (red C, blue) or White Sox (black) jersey on someone or in a shop. Photograph the kit.
Spot a Garrett popcorn bag
Find a Garrett Popcorn shop or souvenir bag with the iconic caramel-cheese mix. Photograph the orange bag.
Spot a Magnificent Mile flagship
Walk Michigan Avenue and find a Magnificent Mile flagship store (Apple, Nike, Disney). Photograph the storefront.
Spot a Wicker Park mural
Walk into Wicker Park and find a mural on Damen Avenue or a side street. Photograph the wall.
Spot an American flag in Chicago
Find a US flag on a Chicago building. Photograph it.
Spot an Italian beef sandwich
Find an Italian beef sandwich (Al's, Portillo's, Mr. Beef). Photograph the dipped roll.
Spot Buckingham Fountain
Walk to Grant Park and find Buckingham Fountain with the central jet. Photograph the spray.
Spot the Chicago city flag
Find the Chicago flag (white with two blue bars and four red stars). Photograph it.
Spot the Chicago River green (St. Patrick's only) or normal blue
Find a vantage of the Chicago River. Bonus points if it's St. Patrick's Day and the river is dyed green. Photograph the water.
Spot the Chicago Riverwalk
Walk along the Chicago Riverwalk and find a vantage with bridges and skyscrapers. Photograph the river.
Spot the Chicago Theatre marquee
Find the Chicago Theatre marquee on State Street (the giant red CHICAGO sign). Photograph the marquee.
Spot the Cloud Gate (the Bean)
Walk to Millennium Park and find Anish Kapoor's Cloud Gate. Photograph the team reflected in the silver bean.
Spot the Crown Fountain video face
In Millennium Park find the Crown Fountain with a video face spitting water. Photograph the face.
Spot the Picasso (Untitled) sculpture
Find Picasso's untitled sculpture on Daley Plaza. Photograph the bronze figure.
Spot the Tribune Tower stone embed
At the Tribune Tower on Michigan Avenue find an embedded stone from a famous building (Acropolis, Great Wall). Photograph one.
Spot the Willis Tower (Sears)
Find a view of the Willis Tower (the former Sears Tower) skyscraper. Photograph the silhouette.
Spot Wrigley Field facade
Find Wrigley Field exterior, with the marquee saying "Wrigley Field Home of Chicago Cubs". Photograph the marquee.
Trivia: Deep dish year
Deep dish pizza was invented in Chicago. In what decade did it first appear (just the decade, e.g. 1950s)?
Trivia: Great Chicago Fire
In what year did the Great Chicago Fire destroy most of the city?
Trivia: The Bean artist
Cloud Gate, the Bean, was sculpted by which famous British-Indian artist?