Chicago Area Mystery Day Road Trip

Chicago, Illinois

Chicago Area Mystery Day Road Trip

Chicago, Illinois

Duration: 8 hours

Package: Road Trip Kit

Overview

Explore Chicago’s best-kept secrets with a self-guided trip through scenic landscapes, historic sites, and quirky attractions. Perfect for adventurers, this mystery itinerary reveals each destination as you go.

🗺️ Self-paced day trip through Chicago’s unexpected attractions

📍 Discover cultural sites, scenic views, and quirky neighborhoods

💌 Locations revealed as you go for an exciting, surprise-filled experience

🌍 Complete with an elegantly designed trip bundle and guidebook

🚗 Ideal for locals and visitors seeking a fresh look at Chicago

Availability

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily

Full description

Get ready to discover Chicago in a whole new way! This mystery day trip leads you through the city’s hidden gems and lesser-known sites, revealing each surprise destination one by one. Perfect for both locals and newcomers, this self-guided adventure uncovers Chicago’s less-traveled spots, from scenic urban vistas and historic neighborhoods to cozy cafés and unique landmarks.

Before you set off, you’ll select a theme based on your location, interests, and travel preferences—whether you’re drawn to art, food, history, or nature, there’s a Chicago adventure that’s just right for you. Once you’ve chosen, a beautifully crafted trip kit will be sent to your door. Inside, you’ll find sealed envelopes (one for each stop) and a “Before You Go” guide, filled with packing tips, essential info, and everything you need for a smooth day of exploring.

At each stop, open a new envelope to uncover carefully selected recommendations, insider tips, and fun facts that bring each location to life. Whether you’re visiting scenic lookouts, hidden art installations, or quaint local eateries, each destination showcases a unique side of Chicago’s vibrant personality. This trip is perfect for couples, families, or friends who want to explore the city together in a fun, surprising way.

Practical information

Any restrictions to participate?

Age: All age groups are welcome.
License: Participants must have a valid driver’s license and drive their own vehicle.
Experience level: This experience is suitable for all levels; no prior experience is required.

Who can you accommodate for?

Children: All participants must pay to participate, children included.
Individuals with disabilities: Accessibility varies by destination; please check in advance for specific accommodations.
Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

Duration: This self-guided experience lasts up to 8 hours, depending on the time spent at each stop.
What’s included: A well-curated itinerary and beautifully crafted booklet with directions, destination hints, and details on small businesses, hidden gems, and unique local spots.
Who will be present: This is a private experience exclusively for you and your group. It is entirely self-guided, allowing you to explore at your own pace without a tour guide.
Photo/ video: You’re welcome to take photos along the way to capture memories of your unique road trip.
Specific rules to follow: You must use your own vehicle and follow traffic and parking regulations.

How to prepare?

Weather dependency: This experience is not weather dependent; it runs rain or shine.
Arrival: Begin your trip at your convenience. Instructions will be provided ahead of time for a seamless start.
Parking: Parking availability varies by stop. Plan accordingly for any parking fees.
What to wear: Comfortable clothing and walking shoes are recommended; dress for expected weather conditions.
What to bring:
- Water, snacks, and any essentials for a day on the road
- Fully charged phone to access instructions and digital content
- Personal items and cash or card for any additional purchases along the route

Additional Information

What's not included: Fuel, parking fees, attraction entrance fees, food, and drinks are not included.
Shipping: Shipping is free (5-7 business days via expedited mail). Xpresspost shipping is available for $10 USD / $12 CAD, delivering in 2-5 business days.
Experience Provider: Detailed information about your Experience Provider will be provided in your booking confirmation email, ensuring peace of mind and quality throughout your trip.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

Once your booking is confirmed, it is final. Cancellations or rescheduling requests are not permitted. If you do not appear on your booked date, the value of your experience will be forfeited. However, if your tour is canceled due to inclement weather, you may reschedule directly with the experience provider.