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Chicago

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  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 USD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • CYCLE FRIENDLY
    A Riverside Ramble

    A Riverside Ramble

    $39 USD
    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!
    • Accessible
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • GREAT FOR FAMILIES
    A person standing by a body of water, taking a photograph with a camera, surrounded by trees with autumn leaves.

    All Things Charming

    $39 USD
    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.
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • Dog-Friendly Trip!
    A scenic view of a waterfall surrounded by rocks and greenery, likely taken during a day trip in a forested area.

    Falls, Forests & Fables

    $39 USD
    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!
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Chicago Area
  • BEST DONE SPRING-FALL
    Lakeshore Views & Brews

    Lakeshore Views & Brews

    $39 USD
    Stroll along a breathtaking boardwalk, dip your does 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.
    • Kid-Friendly
    • Accessible
    Can depart from: Chicago Area
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $39 USD
    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.
    • Dog-Friendly
    • Accessible
    Can depart from: Chicago Area
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $39 USD
    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.
    • Kid-Friendly
    • Accessible
    Can depart from: Chicago Area, Milwaukee Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!