Chicago & Milwaukee

One-day, surprise, self-guided road trips now available in Illinois and Wisconsin!

Now Available!

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How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

  • Select your trip style.

    Select a day trip based on your location, interests, and travel preferences OR take our quiz to help narrow down options.

  • Get your package.

    Choose between receiving a beautifully crafted package in the mail OR a PDF (digital version) of the trip which gets sent right to your inbox.

  • Pack your car.

    Each package includes a ‘Before You Go’ booklet that will give you just enough information without spoiling the surprise destinations on your road trip.