Chicago Photo Contest Winners Announcement!

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


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

Book a chicago event

Let’s Connect!