Chicago’s reputation as a city of architecture, music, and storytelling makes it a fantastic place for exploring through guided tours. Whether you’re interested in the glamour of historic theaters, the spooky stories lurking in city shadows, or discovering hidden corners with a smartphone app, Chicago offers something for every curiosity. Among the options, we especially love the Chicago Theatre Tour Experience for its behind-the-scenes look at a landmark venue, and Ghosts & Hauntings for those who thrill at ghost stories and spooky legends. These tours provide a closer look at the city’s soul—whether through grand architecture or ghostly tales.
Ready to explore? Below, you’ll find a quick overview of the best tours in Chicago, each with its own unique flavor, from theatrical history to haunted mysteries and interactive city walks.
1. The Chicago Theatre Tour Experience
At number one, the Chicago Theatre Tour Experience takes you inside one of Chicago’s most iconic landmarks. For $26 per person, this one-hour tour offers an intimate look at the grandeur of what’s called the “Wonder Theatre of the World.” The tour includes a walk through the magnificent six-story marquee, detailed explanations of the beautifully preserved architecture, and a chance to marvel at historic murals.
What truly makes this tour stand out is the opportunity to step onto the stage and imagine what it’s like to perform in front of thousands, along with meeting a Rockettes-style dancer—adding a touch of Hollywood glitz. The reviews consistently praise the professionalism and friendliness of the guides, as well as the chance to see behind the scenes of a place where countless stars have performed. For theater lovers or anyone interested in Chicago’s entertainment scene, this tour offers a rich, visual history.
Bottom line: For an affordable peek into Chicago’s theatrical past and a chance to stand where legends once performed, this tour hits the sweet spot—especially given its high rating of 4.7/5 from nearly 90 reviews.
2. Chicago: Ghosts & Hauntings of the Windy City Walking Tour
Next, the Ghosts & Hauntings of the Windy City Walking Tour offers a different kind of Chicago experience—one filled with spooky stories and haunted lore. For $27, this one-hour tour by US Ghost Adventures walks you through Lincoln Park, revealing ghostly tales of gangsters, serial killers, and the restless spirits believed to haunt the neighborhood. You’ll also explore beneath the park to learn about the forgotten burial grounds, and catch glimpses of the Victorian woman in white near Lincoln Park Zoo.
What makes this tour appealing is the combination of history and storytelling, delivered by a guide praised for her engaging style. Guests mention that the spooky stories are well told and that the tour feels personal, making it an ideal choice for those fascinated by Chicago’s darker side. The tour’s reviews highlight its balance of fun, fright, and factual storytelling, making it a memorable way to see a different side of the city.
Bottom line: If ghost stories and the macabre intrigue you, this tour offers a lively, spooky walk with a knowledgeable guide at a reasonable price, earning a solid 4.4/5.
3. Michigan Avenue Rendezvous Walking Tour with Smartphone App
For those who prefer a flexible, tech-savvy approach, the Michigan Avenue Rendezvous Walking Tour with Smartphone App provides an interactive experience. Priced at $18, it allows you to explore the famed Magnificent Mile at your own pace, guided by a location-based scavenger hunt delivered through your mobile device.
This tour is best suited for travelers who enjoy discovering hidden corners and landmarks without rigid schedules. The app includes clues and fun facts that lead you through Chicago’s shopping districts, public art, historic buildings, and lesser-known sights. Since it’s self-directed, it’s perfect for small groups or families who want to mix sightseeing with a bit of adventure.
However, with only three reviews for now, the experience might lack the detail of guided tours, but the interactive element is a good fit for tech-minded explorers. It’s a cost-effective way to get your bearings and discover Chicago’s streets on your terms.
Bottom line: Ideal for independent travelers who want an engaging, flexible city experience, especially if you have a smartphone and an adventurous spirit.
How to Choose the Best Tour for You
When deciding between these options, consider your interests and how much time you want to spend. If you love history and architecture, the Chicago Theatre Tour offers an inside look at a grand venue. For thrill-seekers or those intrigued by Chicago’s darker stories, the haunted Ghosts & Hauntings Tour delivers spine-tingling tales. Meanwhile, if you prefer a customizable experience or are short on time, the Smartphone App Tour lets you explore at your own pace with interactive features.
Budget-minded travelers will appreciate the affordability of the theater and ghost tours, both under $30, while those seeking a more personalized or flexible experience might prefer the app-based walk. Book early, especially for popular tours, and check availability to ensure the times align with your schedule.
Final Thoughts
Chicago offers a wide range of tours that reveal its architectural splendors, haunted secrets, and lively streets. For a glimpse into its theatrical past, the Chicago Theatre Tour Experience provides a beautifully curated backstage pass. For a darker twist, the Ghosts & Hauntings Tour brings ghost stories to life amid historical sites. And for those who love exploring independently, the Michigan Avenue Smartphone Tour offers a fun, interactive way to uncover the city’s hidden corners.
Whether you’re a history buff, a thrill-seeker, or a tech explorer, these tours help you see Chicago through different lenses. To make the most of your trip, consider your interests and schedule, and book early—some tours fill up quickly during peak season. With so many options, your Chicago adventure will be full of memorable stories and discoveries.