Self-Guided Walking Tours in Chicago
Explore at your own pace with app-guided clues, puzzles, and hidden stories.
Walk through Chicago with Questo's self-guided walking tours. Follow clues along the Riverwalk, through the Loop's canyon of skyscrapers, and into the jazz clubs and speakeasies of the neighbourhood streets. Architecture, crime, and hidden history — all on your phone, no booking needed.
Upcoming Events in Chicago
Limited-time adventures — book before they're gone
Coming to Chicago
Dorothy’s Quest: The Trials of Oz in Chicago
Solve puzzles from the characters of the Emerald City. A real-world adventure through your city’s streets.
All quests in Chicago
Eastside Chicago: The Art Heist Walking Tour & Escape Game
3.4 km | Avg. time: 95 min
4.73 (179 reviews)Ghosts of Chicago: Haunted Lincoln Park Walking Tour & Escape Game
2.7 km | Avg. time: 80 min
4.67 (173 reviews)The Oz Escape in Chicago
2.4 km | Avg. time: 90 min
4.54 (153 reviews)Chicago Loop Highlights: Battle the Supernatural
3.4 km | Avg. time: 42 min
4.36 (11 reviews)Chicago Lincoln Square: The Alchemist’s Spell Quest
3.2 km | Avg. time: 125 min
4.61 (38 reviews)Murder Mystery: Death in the Shadows in Lincoln Park, Chicago
2.4 km | Avg. time: 90 min
4.69 (65 reviews)
What people have to say about quests in Chicago?
Based on 757+ Local Reviews
Dominic Brooks
Chicago Highlights: Story of a Gangster
the landmark to the pope states totally yours not truly yours
aileen velasquez
Eastside Chicago: The Art Heist Walking Tour & Escape Game
first time! highly recommend
Pepe García Salamanca
Kid Quest: Solve the case of the lost senses in Chicago
algo diferente para hacer con nuestras hijas.
Jonathon McIlwain Sr.
Chicago Highlights: Story of a Gangster
fun adventure for the family to learn more about the city
Mz Val D
Murder Mystery: Death in the Shadows in Lincoln Park, Chicago
This was really awesome. We enjoyed ourselves. It was fun and it gave us great exercise and it was nice to get the opportunity to solve some things together and work together.
Davida M
Chicago Chinatown: Quest for the Dragon Kings
I don't think the tips to get where you were going was confusing, but typing the answers in could be, especially when words were spaced in the clue but there was no spaces when entering your answer (like the artist's name for the last puzzle). If you do not know Mandarin, you may not know what the issue is. Also wish it wasn't so much back and forth walking, it could be a little more in a complete circle to save people like me who were already tired from walking elsewhere. Overall nice to learn about Chinatown this way though! I liked learned the facts and seeing the beautiful architecture through this lense instead of just going to look on my own.
Ditch the Boring Dates: 3 Unforgettable Missions in Chicago for Couples
Skip the repetitive coffee dates. Solve clues together and explore the city.
How to join a quest?
1. Pick Your Quest.
Find an adventure that sparks your curiosity.
2. Get the App.
Download & sign up in seconds.
3. Start & Have Fun.
Go to the start point and play!
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Frequently asked questions
How do self-guided walking tours in Chicago work?
How many walking tours are available in Chicago?
Do I need to book a walking tour in Chicago in advance?
What makes a Questo quest different from a regular Chicago tour?
nstead of following a guide with a flag, you explore Chicago at your own pace through an interactive story. Quests take you past landmarks like Millennium Park, the Chicago River, and hidden corners of the Loop—while you solve puzzles and uncover stories along the way. It feels like sightseeing and a game all at once.
I’m a local—are there fun things to do in Chicago this weekend with Questo?
Yes! Even if you’ve lived here your whole life, Questo gives you a reason to rediscover the city. The Chicago Murder Mystery: Death in the Shadows is perfect for an evening with friends or as a weekend date idea. You’ll chase down clues through familiar neighborhoods while solving a case that’s equal parts challenge and fun.
What’s a good Chicago quest for tourists?
For first-time visitors, two quests stand out:
- Eastside Chicago: The Art Heist Walking Tour & Escape Game — Explore Millennium Park, Cloud Gate (“The Bean”), and the city’s art scene while unraveling a thrilling heist storyline
- Chicago Highlights: Story of a Gangster — Walk the streets once ruled by Al Capone and uncover Chicago’s Prohibition-era history. It’s like stepping into a living gangster tale while touring the city’s most iconic spots.
What’s a fun thing to do with kids in Chicago?
Families love Kid Quest: The Day the Senses Went Silent, designed for younger kids (ages 4–8). It turns sightseeing into a playful adventure where children solve puzzles and restore lost “senses” as they explore. It’s one of the best things to do in Chicago with kids because it keeps them entertained while you all discover the city together.
Is Questo a good date idea in Chicago?
Definitely. The Murder Mystery quest is one of the most creative date ideas in Chicago. Couples team up to follow a mysterious storyline, solve clues, and explore the city in a way that’s far more memorable than dinner and a movie. Evening play makes it even more atmospheric.
Can groups of friends play together?
Yes! Quests are designed for collaboration, so they’re great for small groups. Whether you’re celebrating a birthday, looking for weekend plans, or just want something more exciting than another night at the bar, Questo turns Chicago into your own escape game.
Do I need to book a specific time?
Nope—you play on your schedule. Start in the morning, after work, or on the weekend whenever you’re ready. The app guides you, so you can pause for coffee, pizza, or photos and pick back up whenever you want.
Walk through Chicago with Questo's self-guided walking tours. Follow clues along the Riverwalk, through the Loop's canyon of skyscrapers, and into the jazz clubs and speakeasies of the neighbourhood streets. Architecture, crime, and hidden history — all on your phone, no booking needed.
About Chicago
From a murder mystery in Chicago’s historic streets to clue-chasing adventures in Millennium Park, every quest is a mix of sightseeing, storytelling, and problem-solving. You’ll stroll past Cloud Gate (“The Bean”), the Chicago Riverwalk, the Old Water Tower, and charming neighborhoods like Lincoln Square—all while playing at your own pace.
Perfect for couples looking for a date idea, families with kids, groups of friends, or solo explorers, Questo quests turn “things to do in Chicago” into a fun, interactive game. Start anytime, pause for a deep-dish pizza, and see Chicago’s history, culture, and secrets come to life in a way you’ll never forget.