Outdoor Things to Do in Chicago

Explore at your own pace with app-guided clues, puzzles, and hidden stories.

4.6775 reviews in ChicagoTrusted by 1M+ explorersSelf-guided · no booking · play offline

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Upcoming Events in Chicago

Limited-time adventures, book before they're gone

Dorothy’s Quest: The Trials of Oz in Chicago
Limited-Time EventEarly Bird

Dorothy’s Quest: The Trials of Oz in Chicago

June 6, 2026$29.99From $21.99
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How it works

1

Pick a Quest

Find an adventure that sparks your curiosity.

2

Get the App

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3

Start & Play

Go to the start point and have fun!

What people have to say about quests in Chicago?

4.6

Based on 775+ Local Reviews

Dominic Brooks's quest photo

Dominic Brooks

Chicago Highlights: Story of a Gangster

the landmark to the pope states totally yours not truly yours

Verified Player
aileen velasquez's quest photo

aileen velasquez

Eastside Chicago: The Art Heist Walking Tour & Escape Game

first time! highly recommend

Verified Player
Pepe García Salamanca's quest photo

Pepe García Salamanca

Kid Quest: Solve the case of the lost senses in Chicago

algo diferente para hacer con nuestras hijas.

Verified Player
Jonathon McIlwain Sr.'s quest photo

Jonathon McIlwain Sr.

Chicago Highlights: Story of a Gangster

fun adventure for the family to learn more about the city

Verified Player
Mz Val D's quest photo

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.

Verified Player
Davida M's quest photo

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.

Verified Player

Ditch the Boring Dates: 3 Unforgettable Missions in Chicago for Couples

Skip the repetitive coffee dates. Solve clues together and explore the city.

Murder Mystery: Death in the Shadows in Lincoln Park, Chicago
4.69

Murder Mystery: Death in the Shadows in Lincoln Park, Chicago

Chicago Chinatown: Quest for the Dragon Kings
4.5

Chicago Chinatown: Quest for the Dragon Kings

Eastside Chicago: The Art Heist Walking Tour & Escape Game
4.73

Eastside Chicago: The Art Heist Walking Tour & Escape Game

Ways to explore Chicago with Questo

One app, one type of quest — different ways to play it.

As a scavenger hunt

Solve clues and puzzles at real Chicago landmarks. Race against the clock or take it at your own pace — and bring a group to compete for a spot on the leaderboard.

See all Chicago scavenger hunts

As a self-guided walking tour

A GPS-guided walking route with stories along the way. Play on your own schedule, stop and resume anytime — and once you've downloaded a quest, it works fully offline.

See Chicago walking tours

For a spooky twist

Prefer chills over clues? Some Chicago quests lean into haunted history and dark legends after dusk.

See Chicago ghost tours

As a murder mystery

Play detective — investigate suspects, follow the evidence, and crack the case as you explore Chicago.

See Chicago murder mysteries

Cities nearby Chicago

Find a city nearby to play with your family and friends.

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Frequently asked questions

How do self-guided walking tours in Chicago work?
Download the Questo app, pick a walking tour in Chicago, and start walking. The app guides you with GPS to each stop, where you solve a clue or puzzle before moving on. Most tours take 60-120 minutes. No booking needed, start anytime.
How many walking tours are available in Chicago?
Questo currently offers 21 self-guided walking tours in Chicago. Prices start from $5.25 per person.
Do I need to book a walking tour in Chicago in advance?
No, Questo walking tours are self-guided and available anytime. There is no booking, no fixed time, and no guide to meet. Just open the app when you are ready and start exploring Chicago at your own pace.
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

Questo turns Chicago into a self-guided outdoor escape game you play on your phone. You follow a story, solve clues, and let the puzzles steer you block by block, from the lakefront and the Loop out to the neighborhoods, all at whatever pace suits your day.

The quests cover a real range of moods. Some are art-heist capers and escape-game mysteries, some are after-dark ghost hunts around Lincoln Park, and others dig into Chicago's gangster past or spin local folklore through Chinatown and Lincoln Square. Along the way you pass landmarks that locals and visitors both love, like Cloud Gate (the Bean) and Crown Fountain in Millennium Park, the Chicago Riverwalk, Tribune Tower, Buckingham Fountain, and Chinatown Square.

A few local notes worth knowing. Chicagoans will tell you the everyday pizza here is thin tavern-style cut into squares, not the deep-dish tourists expect, so try a square slice at a neighborhood spot. And for the postcard skyline view without a ticket, walk out to the lakefront path by the Adler Planetarium, where the whole downtown lines up across the water.

Questo's Chicago quests are rated 4.61★ across 198 player reviews. They work well for couples after a different kind of date, families keeping kids curious, friends who want a bit of friendly competition, or anyone exploring solo.

Start whenever you like, stop for a coffee or that square of pizza when you need a break, and pick the story back up when you are ready. Open a quest and start playing your way through Chicago.