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Chicago Urban Adventures

  • Work together to solve fun challenges & puzzling clues Perfectly balanced & location-based.
  • Guided by clues sent to your phones Messages sent to you and your team's phones.
  • Explore Chicago's historic landmarks and hidden gems Our speciality, discovering and showing off amazing places!
  • Discover top-rated pubs, bars and cafes - all optional Optional breaks to catch a rest along the way.
  • Compete Set the fastest time and see you ranking on your end certificate. for top spot on the Chicago leaderboard
Talk to us about team building options
Full money back guarantee

Don't have a great time?
Simply let us know why and we'll refund you in full.

Next Steps

1. Select your game, pick a trail of your choice and receive your welcome email.
2. Rally your team and enter a team name and phone number(s) into the system.
3. Receive your welcome text, then head to the start location on a day and time of your choice.
4. Text START to receive the first in a series of cryptic directions. Solve the puzzles to unravel your mystery.
5. Discover unique places, the secret and hidden of your city - and great independant pubs/cafes!

Gift an Experience

Choose from over 125 top-rated experiences across 40 cities, or choose a gift balance for ultimate flexibility. We're happy to switch should your recipient wish to change!

Chicago Experiences

Each trail takes place in a different area of the city - click each tile to learn more!

Lost in the Loop

Lost in the Loop

Architectural giants and secret treasures of the North Loop… more

There are no start time restrictions, start whenever, although we do recommend some daylight!
2 - 3 hours across 4.8 km / 3.0 miles
Pritzker Park to Washington Metro
$20
per person
Chicago Chinatown Hunt
  • Coming soon, get notified

Chicago Chinatown Hunt

A hunt to hit all the senses… more

Start at any time!
1.5 to 2 hours across 3.0 km / 1.9 miles
Fully flexible booking Alter your booking freely;
change the date, time, number of people or game.
$20
per person
Chicago Old Town
  • Coming soon, get notified

Chicago Old Town

Hunt back in time at the 'Cabbage patch'… more

Start at any time!
1.5 to 2 hours across 3.0 km / 1.9 miles
Fully flexible booking Alter your booking freely;
change the date, time, number of people or game.
$20
per person
Magnificent Mile
  • Coming soon, get notified

Magnificent Mile

A magnificent mile at the heart of Chicago… more

Start at any time.
2 hours on average across 3.0 km / 1.9 miles
Fully flexible booking Alter your booking freely;
change the date, time, number of people or game.
$20
per person

Action-packed Urban Adventure Hunts in Chicago

How the Chicago days out work

Discover Chicago's secret places

Experience Chicago's unique places and share stories in independent pubs & cafes, curated for each Chicago Urban Adventure Hunt.

Fun challenges

Engaging puzzles and captivating stories reveal Chicago in a new light.

Play together or competitively

Work as a team or compete head-to-head to set the fastest time on our Chicago leaderboard.

Fully flexible bookings

Alter your booking freely; change the date, time, number of people or chosen Chicago Urban Adventure Hunt. Even stop and start once you've begun.
How it works

Fun activity for all groups

Corporate Treasure Hunts
Work together with friends & family
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Chicago Urban Adventure Hunt Reviews

The great things you say about CityDays Urban Adventure Hunts

Read all our customer reviews

Ready? Book your Urban Adventure Hunt today

How It Works

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