Chicago Highlights: Story of a Gangster image 1

Chicago Highlights: Story of a Gangster

🔒 Instant Access: Book now and start immediately. No need to wait for a guide.

⏱️ Total Flexibility: Start, pause, and resume whenever you want.

🧩 Gamified Discovery: Solve 10 location-based puzzles to unlock hidden stories and secret spots.

📍 Starting Point: Exchequer Restaurant & Pub, 226 S Wabash Ave, Chicago, IL 60604, USA

🛡️ Free Cancellation: Cancel up to 24 hours before your planned start for a full refund.

🌐 Verfügbar in: 🇬🇧 English

Orte, die du besuchen wirst

10

Es wird dich nehmen

57-87 mins

Du wirst gehen

5250 Schritte

Gesamtdistanz

4 km

Route, die du erkunden wirst

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Startpunkt Exchequer Restaurant & Pub
226 S Wabash Ave, Chicago, IL 60604, USA
Zielpunkt Holy Name Cathedral Rectory
730 N Wabash Ave, Chicago, IL 60611, USA

Über dieses Abenteuer

A historic walk that tells the story of Chicago's emergence from the ashes of the Great Chicago Fire.  Your stroll takes you from the heart of downtown north across the river.  

You'll see world-famous landmarks while learning answers to the city's most compelling questions:  Where was the world's first skyscraper?  Why are there two Wacker Drives stacked on top of one another?  

What's the real reason it's called "The Windy City"?  And lest we forget – GANGSTERS!!

What to Expect

This self-guided walking tour in Chicago combines exploration, storytelling, and puzzle-solving into one unique experience. As you navigate through the city, you will discover 10 carefully selected locations, each revealing a piece of the story.

The entire quest takes approximately 4320 minutes to complete and covers 4km on foot. You will move at your own pace, with the freedom to pause whenever you want to take photos, grab a coffee, or simply soak in the atmosphere.

Each location features a challenge or puzzle that unlocks the next chapter of your story. These challenges are designed to be fun and engaging while teaching you about the history, culture, and hidden gems of Chicago.

No tour guide needed – your smartphone becomes your guide. The Questo app provides directions, shares stories, and presents challenges along the way.

Höhepunkte

  • Take in the most interesting sights of the biggest city in America's heartland

  • Hear the story of the most infamous of Chicago sons, Al Capone

  • Starting in the the city's famed Loop, you'll visit iconic sights like the Tribune Tower and the Chicago River

  • Take in the Magnificent Mile and end up in a place where you can still see bullet holes from the city's violent past

Die Mission: Deine Geschichte in Chicago

It’s 1930. Things been tough for your family for the last year, just as it has been for most Americans during the Great Depression.

 ince your father died unexpectedly, it’s up to you to support your family. You heard that Al Capone’s criminal “business” is always looking for help. 
You decide to give it a shot.
  • Not for kids
  • Don’t enter the places, not part of the experience

Tips & Recommendations

👟

Wear Comfortable Shoes

You will be walking throughout the city, so comfortable footwear is essential for enjoying the experience.

🔋

Charge Your Phone

Make sure your smartphone is fully charged. The quest runs through the Questo app, and you will be using it throughout.

🌤️

Check the Weather

This is an outdoor activity. Bring an umbrella or sunscreen depending on the forecast.

📸

Bring a Camera

You will discover photogenic locations and hidden gems perfect for capturing memories.

💧

Stay Hydrated

Bring water, especially during warmer months or longer quests.

👥

Play with Friends

While you can play solo, quests are more fun with friends or family. One ticket works for a group.

Important Information

⏱️

Duration

Approximately 4320 minutes

🚶

Distance

4km walking

👥

Group Size

Unlimited

💪

Difficulty

Easy to Moderate

Accessibility

Not wheelchair accessible (stairs and uneven surfaces)

🔄

Cancellation Policy

Free cancellation up to 24 hours before your scheduled start time

ℹ️

Need to Know Before Booking

  • You will need the Questo app on your smartphone (iOS or Android)
  • Each ticket can be used by a group (share one device or play separately)
  • Internet connection required to download the quest initially
  • Once downloaded, you can play offline if needed

Bewertungen und Rezensionen

4.38

45 Bewertungen

5 Sterne
49%
4 Sterne
42%
3 Sterne
7%
2 Sterne
2%
1 Stern
0%
Bewertungen
Sortiere nach

Dominic Brooks

08 Nov 2025
the landmark to the pope states totally yours not truly yours

Rocio

31 Aug 2025

Jonathon McIlwain Sr.

16 Jun 2025
fun adventure for the family to learn more about the city

Nathalie

07 Jun 2025

FCF

07 Jun 2025

Schlag die Besten: Top-Chicago-Entdecker

KelansauntRookie
3100 XP
FCFSeeker
3100 XP
CHRISTOPHER SURGEN
CHRISTOPHER SURGENSeeker
3100 XP

Questo vs. Geführte Stadtspaziergänge im Vergleich

FeatureGeführte TourenQuesto
Flexibilität
Feste Zeiten, kein Pausieren
Jederzeit starten, pausieren und fortsetzen
Privatsphäre
Bis zu 30 Fremde in der Gruppe
Privates Erlebnis nur für Ihre Gruppe
Preis
$30-$40 pro Person
Günstige Preise pro Gruppe
Verfügbarkeit
Vorabbuchung nötig
Sofortiger Zugang 24/7/365
Erlebnis
Passives Zuhören beim Guide
Aktive Gamification; Sie lösen das Rätsel

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