Transit Tees Holiday Gift Guide: Chicago Gifts Under 20 Dollars

Holiday Gift Guide 2025 for Chicago Fans and Local Shoppers

If you're looking for affordable Chicago themed holiday gifts, you have found the right place. This curated collection from Transit Tees highlights some of the most popular Chicago gifts under 20 dollars. Each item captures a piece of the city’s architecture, transit, culture, or humor. All products are available online and in our Wicker Park and Andersonville stores. Place your order by Wednesday, December 17, 2025 to ensure Christmas delivery.

Top Chicago Architecture Gifts Under 20 Dollars

Chicago Architecture Coloring Book This coloring book features 54 iconic Chicago buildings and landmarks. The illustrations are detailed, relaxing to color, and printed on perforated pages. This makes it a perfect Chicago gift for artists, design lovers, or anyone who enjoys exploring the city’s architecture.

Chicago Architecture Playing Card Deck This unique deck of cards highlights 54 architectural landmarks and turns any card game into a mini tour of the city. It is a great gift for families, travelers, and Chicago enthusiasts who enjoy functional souvenirs.

Best Chicago Ornaments Under 20 Dollars

Mortal Bottle Blown Glass Ornament This hand painted ornament is a playful tribute to a classic local spirit. It adds color, humor, and Chicago character to any holiday tree.

Elevated Train Blown Glass Ornament This ornament captures the look and charm of Chicago’s elevated trains. It is a perfect Chicago ornament for transit fans or anyone decorating with local style.

Chicago Theatre Blown Glass Ornament Inspired by our city’s famous marquee sign, this ornament is a must have for theater lovers and collectors of Chicago memorabilia. 

Practical Chicago Gifts Under 20 Dollars

Chicago Skyline Dress Socks These dress socks feature five recognizable Chicago skyscrapers woven directly into the design. They are comfortable, stylish, and an easy stocking stuffer for anyone who loves the city.

Chicago Skyline Mug This 15 ounce ceramic mug showcases the Chicago skyline and makes a perfect daily coffee or tea companion. It is one of the most giftable Chicago mugs available under 20 dollars.

Wrigley Field Mug and Chicago Theatre Mug

Both of these mugs celebrate two of Chicago’s most beloved landmarks. They are ideal gifts for fans of baseball, performing arts, or classic Chicago imagery.

Shop Chicago Gifts Online or In Store

All of these Chicago gifts under 20 dollars are designed by Transit Tees and available both online and at our Andersonville and Wicker Park locations. Order by Wednesday, December 17, 2025 for Christmas delivery so your gifts arrive in time for the holiday.