5 Great Chicago-Themed Holiday Gift Ideas

Each year holiday shopping gets more and more grueling and, quite frankly, more and more obnoxiously overwhelming. So why not make things a little less crazy by avoiding the brutal throngs of gift buying wack jobs and buy locally with these great Chicago holiday gift ideas from great local businesses.

Of course, you can always just buy tickets for our annual Holiday Tour of Drinks, Daleys and Dead Guys if you’d like an active Christmas gift experience.

1. Chicago-themed Holiday Cards

No matter what holiday you are celebrating this season, some pretty awesome holiday cards may fit your personality. Some of my favorite Chicago-themed holiday cards this year are from Rhymeswithtwee, including this Chicago Bean holiday card and, for the more hard-core Chicagoan, a Malort-themed holiday card. These cards start at $4 for a single and $12 for a set.

chicago holiday card christmas bean
Photo Credit: Courtesy of rhymeswithtwee Etsy shop
chicago holiday christmas card gift malort
Photo Credit: Courtesy of rhymeswithtwee Etsy shop

And for those celebrating Hanukkah, studioLISTED has designed this classic Chicago-inspired at $2.95 per card.

chicago holiday gift card hanukkah
Photo Credit: Courtesy of studioLIFTED Etsy shop

2. Chicago Neighborhood Art

Chicago pride is all about ‘hood. This deconstructed “map” of Chicago neighborhoods cleverly orders each from smallest to largest and creates a print that looks like a cool eye chart. This $35 holiday gift, designed by BlueIsTheLand, is perfect for any Chicago resident with neighborhood pride.

chicago gift idea neighborhood art
Photo Credit: Courtesy of BlueIsTheLand

3. Jo Snow Syrups

How about some local flavor this holiday season? Jo Snow Syrups is a great gift idea for Chicago foodies that love supporting local small businesses. Our favorite product is Jo’s Fig Vanilla Black Pepper Jam. My brother-in-law freaked out about the root beer syrup. This artisan outfit specializes in flavored syrups for anything from cocktails and coffee to even snow cones! And you can get a cute gift bag of three 5oz. syrups of your choice for only $24, perfect for any Chicago fun food lover.

jo snow chicago food holiday gift bag
Photo Credit: Courtesy of Jo Snow website

4. Whimsical Candy

chicago whimsical candy
Photo Credit: Courtesy of Whimsical Candy website

Or for your sweet-toothed friends and family, perhaps some La Dee Dah’s, Nifty Nougats or the peanut buttery goodness of a WowBar! from Whimsical Candy for a holiday gift. Candies range in price, which is great for any size holiday gift budget. If any of you have joined us for our Loop Interior Architecture Walking Tour or our Historic Chicago Walking Bar Tour, you may have had a chance to taste one of Whimsical Candy’s oh-so-yummy caramels. In addition to these being just totally delicious, they are handmade right in downtown Chicago.


5. Chicago Detours’ Ornaments – new this year!

Photo credit: Amanda Scotese

We launched our new online shop this holiday season and are featuring beautifully crafted holiday ornaments. This special gift is a hand-cast architectural detail from the 1920s made by Decorator’s Supply Corporation, which has been crafting beautiful moldings, corbels and the like since 1883. We transformed them into ornaments by hand-painting gold accents and adding the ribbon. Each comes with a tag that shares the historic background of Decorators Supply. Plus, this hand-crafted piece of history won’t break the bank at only $12!

Happy Holidays!

–Chicago Detours Staff


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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

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