Chicago is a city constantly filled with opportunities, but it’s those distinctive events and experiences that truly spark our excitement. If you’re currently in search of unique things to do in Chicago, we have you covered! Whether you’re immersing yourself in a real-life Quinceañera celebration through a play written by the renowned Broadway playwright or checking out the latest winter pop-up, there’s much to do in the city that’s a bit different. Keep reading for our top out-of-the-box experiences to enjoy in Chicago right now.
1. Visit this Tasty and Zelle® winter pop-up with delicious treats this weekend!
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Tasty and Zelle® have teamed up for a delectable adventure featuring a delicious bakery and speakeasy foodie experience that has popped up in the heart of Chicago! Enjoy two distinct spaces, including Plum Crumb, the coziest winter-themed bakery where visitors can enjoy spectacular desserts inspired by Tasty creator recipes. Hidden Crumb, is a not-to-be-missed winter disco-themed speakeasy with curated menus, delectable bites crafted in collaboration with creators like Gideon General, Rie McClenney, and Inga Lam, meet-and-greet opportunities, festive cocktails, and surprise entertainment. It’s a delightful family outing, perfect for friends seeking a culinary adventure, or great for foodies eager to explore unique flavors, but it’s only in town until December 10th!
The Plum Crumb bakery is open to all! To register for the speakeasy, Hidden Crumb on 12/8 and 12/9, click here.
📍Location: Ørkenoy at 1757 N Kimball Ave Floor 1, Chicago, IL 60647 in Humboldt Park
2. Secure your spot at Disney100: The Exhibition!
Disney100: The Exhibition is celebrating a century of the famous brand with an unmissable exhibit in Chicago opening on November 18th, a.k.a Mickey and Minnie’s birthday. Fans will have the opportunity to see the ‘Crown Jewels’ of The Walt Disney Archives, including over 250 works of art, artifacts, costumes, props and other memorabilia.
There’s something for every Disney lover, whether you’re a fan of the classics or the latest releases. Get a closer look at some of your favorite Disney films, from Snow White and the Seven Dwarfs (1937) to Encanto (2021), as well as the latest members of the Disney family, including Pixar, Star Wars, and MARVEL.
3. Feel like you’re at a real Quinceañera at Sweet 15, but with celebrities!
Don’t miss this unique Quinceañera experience! It combines comedy and immersive theater and was created by Rick Najera, a Broadway playwright and award-winning Hollywood screenwriter. He’s known for his work on shows like ‘In Living Color’ and ‘MAD TV’.
This exciting production is packed with laughter, delectable food, refreshing drinks, and a star-studded cast. Spot renowned Cuban-born actor René Lavan, celebrated for his role in Broadway’s ‘Latinologues,’ portraying Eddy. Bryanna Ciera Colón, known for her role in ‘Chicago Fire,’ takes on the character of daughter Sonora. Additionally, international multi-talented superstar Fernando Allende, recognized for his performances in ABC’s ‘The Streets of Los Angeles,’ ‘Murder in Three Acts,’ and NBC’s ‘The Alamo,’ plays the role of Fernando.
The heartwarming ‘Sweet 15’ storyline revolves around the Valderama family, whose patriarch was absent for seven years, beginning when his daughter Sonora celebrated her 15th birthday, essentially missing her traditional Quinceañera. Upon his return, he is determined to rebuild and reunite the family with one condition: they must allow him to plan and host a belated Quinceañera for his now 22-year-old daughter. And guess what? You’re invited!
📍Downtown Chicago
👸🏻💃🌹‘Sweet 15’ celebrates family and second chances—save a seat at the table!
4. Indulge in table-side S’mores at this hotel-lobby-turned-ski-lodge
The Fairmont Chicago has transformed into a cozy and festive winter ski lodge this season, resembling an Aspen chalet rather than a traditional lobby. The Lodge offers a sophisticated après-ski experience with handcrafted cocktails, delightful sweet and savory fondues, and table-side S’mores. Enjoy creative libations like the ‘Espresso Mintini’ and the ‘Fireside Old Fashioned,’ and experience the entertaining creation of the ‘Cinnamon Spice and Everything Nice.’
One of the highlights is making S’mores right at your table, adding a playful touch to the refined setting. Explore exclusive packages like The Spark, The Campfire, or The Hearth, each offering a unique combination of treats. Don’t miss live entertainment on Thursday, Friday, and Saturday nights. Step inside this distinctive winter retreat at The Fairmont Chicago this winter!
📍200 N Columbus Dr, Chicago, IL 60601
🍫🔥✨ Enjoy après ski retreat right here in Chicago
5. Check out the world-renowned photographer Steve McCurry’s ICONS exhibit
Steve McCurry, a highly influential photographer with a career spanning three decades, showcases his work at the limited-time ICONS exhibition in Loyola University Museum of Art (LUMA). Over 80 captivating photographs, including the iconic ‘Afghan Girl,’ which graced the National Geographic cover in 1985, are on display. This exhibition is a must-see for photography enthusiasts.
McCurry’s unique talent shines in his ability to capture the human element in diverse settings, whether among indigenous tribes, refugee camps, or war zones. Explore his iconic images from his extensive journeys across Afghanistan, Pakistan, India, China, and more.
📍Loyola University Museum of Art (LUMA) at 820 N Michigan Ave, Chicago, IL 60611
6. Illusion and art meet at Perceptual Experience
Perceptual artist Michael Murphy is renowned for his captivating, three-dimensional artworks that have left the art world mesmerized—and now, you have the extraordinary opportunity to experience the most extensive collection of Murphy’s creations in Chicago! See ‘Perceptual Experience: The Art Exhibition’ running until January 28th. It’s on our list of top unique things to do in Chicago because the art changes depending on the angle from which you view it.
Murphy’s important work covers a wide spectrum of topics, from whimsical pieces like the luminous ‘Electric Butterfly’ and crowd-pleaser ‘Wow,’ a fan favorite to photograph, to addressing pressing topics such as war and immigration with thought-provoking works such as ‘No War.’ On entry, Chicagoans are challenged to identify the 80 city icons that make up his newest work dedicated to the city.
📍The Shops at North Bridge, 540 N. Michigan Avenue
7-10. Enjoy a magical night of music under the glow of candlelight
For a unique and romantic experience, Candlelight Concerts offers a variety of performances throughout the city and suburbs. Prepare to be mesmerized by stunning renditions of musical genres ranging from jazz, pop, and rock to classical, featuring everything from holiday songs to ’90s alternative and grunge rock classics. All this in a beautiful setting illuminated by hundreds of candles, so be sure to add it to your must-do list!.
Here’s a few of our most highly-anticipated concert picks that are a bit different from how you’d normally hear your favorite singers!
- Candlelight: 1990s Unplugged: A Tribute to Nirvana and More on November 24th at Salvage One
- Candlelight: A Tribute to Coldplay on November 30th at Cafe Brauer
- Candlelight: A Tribute to Juan Gabriel on December 13th at Theater on the Lake
- Candlelight: Holiday Special featuring “Silent Night, “Jingle Bells,” and More with multiple December dates!
11. Step into the Whodunit ‘CLUE: A Walking Mystery’ Experience in downtown Chicago
If you’re looking for unique things to do in Chicago and like a bit of a mystery, see how good your investigation skills are at ‘Clue: A Walking Mystery’ Experience, bringing the classic board game to life for a limited time.
This peculiar experience transports guests into a thrilling adventure where they become detectives, navigating through a real-life setting to solve the perplexing homicide of Mr. Boddy. This interactive production blends storytelling, problem-solving, and teamwork, to create an experience you won’t soon forget!
📍Downtown Chicago
🕵️🚶♀️Snag your tickets here!
12. See a thrilling Broadway show
There’s no need to head to NYC for a vibrant theater scene because Chicago happens to have some of the best productions, musicals, and comedy shows as well. Some shows to put on your list to see this fall include the return of Lin-Manuel Miranda’s Hamilton, Beetlejuice, BOOP! The Musical, and more!
🎭 Find out more about upcoming productions!