Explore Chicago.

Discover Chicago through local stories and clues hidden in the places around you. Pick a walking adventure and explore at your own pace.

Chicago

What players say about Chicago

1 / 3

Selected five-star reviews with player photos. Original words and ratings.

A city walk. With a plot twist.

Don’t just visit Chicago. Play it.

Turn a walk into an adventure with the Questo app. Follow a story, explore real places and solve puzzles along the way.

Chicago
Real streets. Unexpected discoveries.

  • Find places worth noticing

    Look closer at landmarks and corners you might otherwise walk past.

  • Step into a story

    Uncover local stories or take on a fictional mission. You choose the adventure.

  • Solve it together

    Follow clues, connect the dots and share that “we got it!” moment.

Guided by the appPause when you likeYour own people
Back to quests

Places to discover in Chicago

Follow clues through real places and discover the stories behind them. Here’s a glimpse of Chicago.

See all 38 landmarks
Chicago8 quests. One pass.

City Exploration Pass

More of Chicago. More stories to take home.

Get 8 included quests in one pass. Discover places, follow stories and solve puzzles at your own pace.

Explore on footPlay your way through the city

One passUSD 39.99

Explore the Chicago pass
See included quests, access details and pricing before you buy.

The people behind the places

Your city has stories. Meet its storytellers.

Discover Chicago through the eyes of the people creating its quests. Their curiosity becomes your next adventure.

From an idea to a quest you can play
CreatedReviewedPlay-tested

Quests are reviewed and play-tested before they become paid experiences.

Your city. Your stories. Someone’s next adventure.

Know a corner of Chicago worth discovering? Build a quest, earn when people play, and help turn your city into a playground.

Become a creator

Questo City Stories Index

Chicago, measured on foot.

Explore its stories, places and walking data, and see how Chicago compares with other cities.

Keep exploring

Where next?

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

Oak Park

2 quests

Evanston

1 quest

Downers Grove

1 quest

Glen Ellyn

1 quest

Naperville

9 quests

Joliet

2 quests

A walk with a plot twist

Look up.
Lean in.
Play along.

Find a quest. Follow clues in the app. Discover the city as you play.

  1. 1

    Choose your quest

    Pick a city, a story and your language.

  2. 2

    Explore and solve

    Follow the app. Find clues in the streets.

  3. 3

    Go at your pace

    Stop for coffee. Pick up where you left off.

A taste of the challenge
01 / Word riddle

Name the creature.

I’m a majestic beast, swift and bold,
In fields of green, my tale unfolds.

A noble creature, with hooves that prance,
A symbol of freedom in every glance.

I can move swiftly, by day or night,
Chasing the wind, my spirit takes flight.

Though I may be pure, like snow, of course,
Can you guess what I am with my grace and force?

A sample game riddle. City exploration quests also reveal real places and local stories.

Before you head out

Your Chicago questions.

What can I do in Chicago with Questo?
Browse outdoor city games built around Chicago. Each quest has its own route and story: follow clues, solve puzzles, and discover the city as you play.
How many outdoor city games are available in Chicago?
Questo currently lists 22 outdoor city games in Chicago. Browse the collection to compare stories, routes, and access options.
Is there a murder mystery game in Chicago?
Yes. Questo has murder mystery quests set on the real streets of Chicago: follow the clues, question the evidence, and solve the case at your own pace. No actors, no booking, start whenever you like.
Is there a scavenger hunt in Chicago?
Yes. Questo's scavenger and treasure hunts take you across Chicago clue by clue, from famous landmarks to hidden corners. Play solo or as a team, starting whenever you like.
Do I need to book an activity in Chicago in advance?
Most Questo quests can be started when you are ready. Select a quest to check its route and access options before you play.
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.

About the destination

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.
Your Chicago story starts outside.Let’s explore.

Your next story starts outside.

Your next adventure is an app away.

Get the Questo app. Pick a quest, follow the clues and make the city your playground.

Download Questo on the App StoreGet Questo on Google Play