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Chicago Photo Contest Winners Announcement!

By Amanda on February 2, 2012


February marks the beginning of our new Good Times Historic Bar Tour, which we are offering for the month of February, so we thought we would reflect on the photo contest we offered with the Grand Prize of a Private Bar Tour for the winner and 12 friends. The stipulation for the contest was to submit “your idea of a good time in Chicago.”

We received quite an interesting variety of photos! Submissions included the following subjects, among many others: various festivals, babies in various locations, lighting fixtures, beach volleyball, Christkindlmarket, the Picasso sculpture, people at parties, a variety of skylines, Paul McCartney with the Cubs, and Benny the Bull (which I had to look up, showing you how much I know of Chicago Sports).

While you can view the four winners here, which we posted last week, we appreciate how everyone who submitted a photo shared their vision of Chicago with us, and most importantly — their idea of a good time in Chicago. We thought it would be fun to make up some fictional contests where these winners would have triumphed.

The Most Colorful Photo Contest

Colors of Chicago

“Flower Market” by Becci Ray

I love this photo! What a moment to capture.

The Most Photoshopped Photo Contest

Chicago Skyline

“Summertime at Buckingham Fountain”

by Carolyn Beland

A candy color skyline view. We like it!

The Most Expressive of a Bad Time in Chicago Photo Contest

Cold Chicago Winter Activity

“Snow Day” by Joshua Covell

While I didn’t judge the photo contest, I certainly watched the images come in, and this one to me was hands-down the most striking with that color peeking out of the blanket of white. Could you imagine being there? The wind chill surely must have made it felt below zero. For this reason I’m sure many of you would agree that the frigid moment captured in this stunning photo expresses more a bad time than a good time!

Most Unique Angle Photo Contest

Chicago Detours Photo Contest

“Squirrel in the Backyard”

by Shiloh Aderhold

There’s a squirrel in here somewhere, though it’s a “Where’s Waldo” to spot him, and I believe he must be having a good time. Most submissions were shot head-on or with a slight upward or downward tilt, and this is the only top-down shot (or at least from the second floor window we think). It isn’t the most visually stimulating photo, but gets an A+ for the creative angle!

Most Scary Photo of Chicago Contest

Chicago View from Tour

“Watching the Storm” by Scott Baker

Wow! Looks like the gates of hell opened up in the sky. Was Blago back in town for this picture?

What an incredible view.

Most Delicious Good Time of Chicago Photo ContestIce Cream Fun in Chicago

“Bobtail Ice Cream” by Amber Gibson

This probably needs no explanation. The photographer says that it’s Bobtail Ice Cream. Looks like someone had a good day in downtown Chicago. You can see Buckingham Fountain in the background.

Most Representative of the Good Times Historic Bar Tour Photo Contest

Off the Beaten Path in Chicago

Ok, this really wasn’t a submission to the contest. It’s a picture from the Good Times Historic Bar Tour. It’s already selling out, so make sure to purchase your tickets soon if you are planning on joining us on this walking tour, which we are offering only in February for now. We stay indoors 90% of the time, visit three historic bars, share iPads with historic photos, and indulge in light appetizers while learning about Chicago’s party and entertainment history. It’s part architecture tour, part history tour, part having drinks with new friends. And it’s great as a private tour for birthday parties, corporate events, special parties, and family reunions. Feel free to email or call if you’d like to be put on a wait-list for any sold-out dates.

Again, thanks to all who submitted to our Photo Contest!

— Amanda Scotese, Chicago Detours Executive Director


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


Call: 312.350.1131
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