Bridge over the Chicago River
The Chicago River is the only river in the world that flows backwards (the engineers reversed it in 1900). Stand on a bridge over the river and take a group photo with the water and the skyline behind you.
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Architecture pose
Chicago is the birthplace of the modern skyscraper. Find an impressive building or a striking facade, line the team up at its base and take a photo where everyone is mimicking the shape or angles of the building.
Checkpoint: Chicago Riverwalk
Navigate to the Chicago Riverwalk along the Chicago River. Check in once you can see boats passing under one of the bridges.
Checkpoint: Cloud Gate
Navigate to Cloud Gate, the giant mirrored sculpture better known as The Bean, in Millennium Park. Check in once your team can see itself reflected.
Checkpoint: Navy Pier
Navigate to Navy Pier on Lake Michigan. Check in once you can see the Ferris wheel reaching for the sky.
Checkpoint: Willis Tower
Navigate to the foot of Willis Tower (you may know it as Sears Tower). Check in once the whole team is craning their necks upward.
Chicago local guide
Convince a real Chicagoan to share one favourite neighbourhood, hidden gem or strong opinion. Take a photo with your impromptu city guide and remember the tip.
Deep dish challenge
Chicago invented deep dish pizza. Find a slice (or a whole pie) at any pizzeria, share it with the team and take a photo where everyone takes a bite at the same time. The cheesier the pull, the better.
Group finale in Chicago
The final challenge! Find a beautiful Chicago spot (the river, the lakefront, in front of The Bean) and take an amazing group photo with the whole team in shot. A photo for the ages, well done everyone!
L-train spotting
The Chicago "L" trains thunder right between the buildings of the Loop. Find a stretch of elevated track and take a group photo with a train passing overhead, or with the steel structure behind you.
Lake Michigan team shot
Navy Pier puts the whole team right next to Lake Michigan. Find a good viewpoint and take a group photo with the lake stretching to the horizon behind you.
Lakeside cheers
Find a spot with Lake Michigan, the river or the Chicago skyline behind you, grab a drink and take a group toast photo. To the Windy City!
Magnificent Mile shot
The Magnificent Mile on Michigan Avenue is the shopping spine of Chicago. Find a stretch of the avenue, take a group photo with the historic Wrigley Building or the skyline behind you and pose like a millionaire on a casual stroll.
Reflection in The Bean
Cloud Gate gives you the best free mirror in the world. Take a group photo where the entire team is visible in the curved reflection of The Bean. Get creative with poses.
Skydeck pose
At the foot of Willis Tower, take a group photo where everyone leans backwards trying to fit the entire tower in the shot. Bonus points if you all pretend to dangle from the famous glass Skydeck ledge.
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?
Trivia: Willis Tower height
The Willis Tower has 110 floors and was once the tallest building in the world. How tall is it in feet (rounded)?
Windy City kick-off
The hunt begins! Find a typical Chicago backdrop (the river, an L-train track, a steel skyscraper) and take a group photo where everyone jumps in the air. Everyone off the ground or it does not count.