Chicago Area Mystery Day Road Trip

Chicago, Illinois

Chicago Area Mystery Day Road Trip

Chicago, Illinois

Duration: 8 hours

Package: PDF Digital Version

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

Discover Chicago’s hidden gems with this mystery day trip! Perfect for locals and visitors, this self-guided adventure reveals scenic vistas, historic neighborhoods, cozy cafés, and unique landmarks—one surprise stop at a time.
Start by selecting a theme that suits your interests—art, food, history, or nature—and receive a trip kit with sealed envelopes for each destination and a “Before You Go” guide packed with tips and essentials.
At each stop, open an envelope to reveal curated recommendations, insider tips, and fun facts. Ideal for couples, families, or friends, it’s a fun and surprising way to explore Chicago!
Choose from a variety of themed day trips departing from the Chicago area, each designed to cater to different interests and preferences. Here are the available trips:

Eerie Escapes: Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home. This trip is dog-friendly, accessible, and can be done in winter.
A Riverside Ramble: Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up! This trip is accessible, kid-friendly, and can depart from the Chicago or Milwaukee areas.
All Things Charming: From serene lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group. This trip is kid-friendly and can depart from the Chicago or Milwaukee areas.
Falls, Forests & Fables: Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring! This trip is dog-friendly, kid-friendly, and can depart from the Chicago area.
Lakeshore Views & Brews: Stroll along a breathtaking boardwalk, dip your toes in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city. This trip is kid-friendly, accessible, and can depart from the Chicago area.
Cinema & Scenery: Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm. This trip is kid-friendly, accessible, and can depart from the Chicago or Milwaukee areas.

Eerie Escapes: Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home. This trip is dog-friendly, accessible, and can be done in winter.
A Riverside Ramble: Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up! This trip is accessible, kid-friendly, and can depart from the Chicago or Milwaukee areas.
All Things Charming: From serene lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group. This trip is kid-friendly and can depart from the Chicago or Milwaukee areas.
Falls, Forests & Fables: Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring! This trip is dog-friendly, kid-friendly, and can depart from the Chicago area.
Lakeshore Views & Brews: Stroll along a breathtaking boardwalk, dip your toes in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city. This trip is kid-friendly, accessible, and can depart from the Chicago area.
Cinema & Scenery: Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm. This trip is kid-friendly, accessible, and can depart from the Chicago or Milwaukee areas.

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

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

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.
Please note: The printed booklet is currently unavailable, but the PDF version is available and will be delivered via email once booking is confirmed.
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 (15 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.

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.
Please note: The printed booklet is currently unavailable, but the PDF version is available and will be delivered via email once booking is confirmed.
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 (15 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.

What is a Mystery Road Trip?
A mystery road trip is a self-guided, one-day adventure that eliminates the hassle of planning. Each trip is crafted around a unique theme, offering hints about the day's journey while keeping the exact destinations a delightful mystery. Expect to discover hidden gems, charming towns, unique cafes, and more along the way.
How Will I Know Where I’m Going?
While the trips are designed to keep you guessing, you’ll have ways to prepare:

Trip Map: Check the general area where the trip ends to ensure it suits your preferences.
FAQs: Each trip page includes FAQs with details like approximate driving distances.
Personalized Help: Reach out for tailored suggestions based on your starting location and interests.
What’s Included in the Package?
Every trip package includes a curated itinerary highlighting small businesses, local attractions, and scenic stops. Costs for food, drinks, gas, and admissions are not included, so you can choose what fits your style.
Can I Bring a Group?
Absolutely! One package covers your entire group. If you’re traveling in multiple cars, consider getting one itinerary per vehicle for convenience.
How Long Are the Trips?
Each trip typically lasts 6-8 hours, including travel and stops. Recommendations for start times are provided to make the most of your day.
Can I Turn This Into an Overnight Trip?
Yes! While designed as single-day adventures, they can easily be extended. Your confirmation email will include hotel suggestions at the final destination.
What Should I Do to Prepare?
The "Before You Go" guide contains all the tips and essentials to ensure you’re ready for the day. Check for updates before you head out to ensure everything runs smoothly.
Do the Trips Expire?
Trips are best enjoyed within six months of purchase to ensure the most up-to-date recommendations. They can still be used later, but some details may change over time.
Are Weekday Trips Possible?
Yes, though many trips are better suited for weekends when more attractions are open. If planning a weekday trip, check for availability at specific stops.
Are the Trips Kid-Friendly?
Most trips are family-friendly, with shorter driving distances recommended for younger travelers. Options for children are available even on trips featuring adult-oriented stops.
Can I Bring My Dog?
Many trips are dog-friendly, with stops that welcome pets. However, some locations like cafes and shops may not allow dogs indoors.
Can I Gift a Road Trip?
Absolutely! These trips make great gifts for anyone who loves discovering new places!

Trip Map: Check the general area where the trip ends to ensure it suits your preferences.
FAQs: Each trip page includes FAQs with details like approximate driving distances.
Personalized Help: Reach out for tailored suggestions based on your starting location and interests.
What’s Included in the Package?
Every trip package includes a curated itinerary highlighting small businesses, local attractions, and scenic stops. Costs for food, drinks, gas, and admissions are not included, so you can choose what fits your style.
Can I Bring a Group?
Absolutely! One package covers your entire group. If you’re traveling in multiple cars, consider getting one itinerary per vehicle for convenience.
How Long Are the Trips?
Each trip typically lasts 6-8 hours, including travel and stops. Recommendations for start times are provided to make the most of your day.
Can I Turn This Into an Overnight Trip?
Yes! While designed as single-day adventures, they can easily be extended. Your confirmation email will include hotel suggestions at the final destination.
What Should I Do to Prepare?
The "Before You Go" guide contains all the tips and essentials to ensure you’re ready for the day. Check for updates before you head out to ensure everything runs smoothly.
Do the Trips Expire?
Trips are best enjoyed within six months of purchase to ensure the most up-to-date recommendations. They can still be used later, but some details may change over time.
Are Weekday Trips Possible?
Yes, though many trips are better suited for weekends when more attractions are open. If planning a weekday trip, check for availability at specific stops.
Are the Trips Kid-Friendly?
Most trips are family-friendly, with shorter driving distances recommended for younger travelers. Options for children are available even on trips featuring adult-oriented stops.
Can I Bring My Dog?
Many trips are dog-friendly, with stops that welcome pets. However, some locations like cafes and shops may not allow dogs indoors.
Can I Gift a Road Trip?
Absolutely! These trips make great gifts for anyone who loves discovering new places!

Unused Experience Vouchers can be returned within 15 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.

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

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