Chicago Quests: Explore with Treasure Hunts & Self-Guided Tours

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.

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.

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.

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.

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.

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.

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.